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Bend Holiday Rentals

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    Travellers to Bend are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    All 132 Rentals in Bend
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    Tumalo Pines1 / 36
    (10)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Second Street Cottage-secluded downtown Bend, OR1 / 27
    (60)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Beautiful Riverfront home1 / 10
    (12)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Mt Bachelor Village -Top floor with 2 Queen beds +1 / 23
    (7)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Parking
    • DVD Player
    • Grill
    • Hot Tub
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 September 2016
    The condo was as advertised: nice place with ample room and great location❗️ Kitchen a bit small but good for stays of a week or less. The owners (Tim and Nicole) were very nice...
    Reviewed 28 August 2014
    I stayed with my partner and his two teenage boys for three nights. We found everything was just as described with the rental, and it was a good amount of space for four people...
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    About this property
    Exceptional value @ Mt Bachelor Village Resort this upstairs unit (no elevator) with 2 REAL queen beds. No sofabeds here but there are 2 queen beds and an additional small roll-away single bed. This is a tastefully updated and exceptionally clean unit in a resort setting. Much better than a...
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    Bend, Central Oregon 97702
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Private Garden
    • Secure Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Two bedroom, one bath apartment above a horse barn in Alfalfa. Alfalfa is Centrally located between Bend, Redmond, and Prineville. We are 20 min East of Bend, 35 min South East of Redmond and same for Prineville. Apartment has beautiful views of the Cascade Mountains as you sit on back porch on...
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    Bend, Central Oregon 97701
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Stroll the River or downtown from this Condo- In the heart of Bend1 / 15
    (5)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 days ago
    This unit is a peaceful setting in the treetops next to the gorgeous Deschutes river park and an easy walk or bike ride to town. It is beautifully decorated and the bed and...
    Reviewed 11 November 2017
    Besides some issues w heat, this was a nice unit and very good communication with the owner! Nicely decorated and good layout. Within a mile of downtown, perfect. There was...
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    About this property
    This place has it all, super convenient and accessible to all of the amenities you want when you visit Bend. A stone's throw from the Deschutes River and it's miles of walking trails, a 5 minute walk to downtown, quick access to the Bend Parkway, and adjacent to restful Pioneer Park and of...
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    Bend, Central Oregon 97701
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Mt.Bachelor Village Resort--Comfortable living1 / 14
    (7)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Balcony
    • Patio
    • Wi-Fi
    • DVD Player
    • Mountain Views
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 September 2017
    If you're looking for a quiet and out of the mainstream place, this is it!The surroundings are amazing.There are trails for walking and a short distance from water sports.I...
    Reviewed 6 July 2016
    This place was Nice. We enjoyed it. It had exactly what was needed.This place was clean and close to town.We had an enjoyable stay here and felt safe. The only drawback I...
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    About this property
    Located on Bend's westside, a short walk along the Deschutes to the Old Mill district and off the Cascade lakes road to Mt.Bachelor, this cozy, recently upgraded condo in Mount Bachelor Village is a convenient base for any recreation or vacation plans. Features a full kitchen with stainless steel...
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    Bend, Central Oregon 97702
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Three Rivers Retreat near Sunriver1 / 22
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Hot Tub
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 May 2014
    We really enjoyed our stay. Great location right on the river. We had a blast with the kayaks and the jacuzzi. The fire pit was great. The beds were comfortable, cabin was well...
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    About this property
    Enjoy the comfort and serenity waiting for you at this peaceful home with views to the Big Deschutes River. Watch ducks stirring the water or a heron standing nearby. Listen to geese pierce the calm as you absorb the tranquil beauty of this natural setting. With easy access to Mt. Bachelor, come...
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    Bend, Central Oregon 97707
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    7th Mountain Resort in Bend, Or1 / 21
    (2)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
    • Wi-Fi
    • DVD Player
    • Children's Pool
    • Air Conditioning
    • Sauna
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 July 2016
    Checking in was our first Summer Time Delight. My friend loved the Iced Tea and shared one with me. And yes it was indeed the best ice tea we ever had. Made just right not too...
    Reviewed 3 September 2015
    My adult daughter and I stayed at Karen's condo at Seventh Mountain for 2 nights and had a wonderful time. I have stayed at Seventh Mountain resort many times and in several...
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    About this property
    Very clean, light and comfortable, well furnished one bedroom two full baths/shower/tub. Sleeps 4 very comfortably. Includes all utilities, wifi, basic cable, land line and use of all amenities. Fireplace ( presto log only), balcony with Deschutes Forest views and of the Paulina's. On site you...
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    Bend, Central Oregon 97702
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Luxury and Comfort at Mount Bachelor Village Condo, Views, Mountains and Lakes!1 / 42
    (5)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 June 2017
    We were wowed by our initial first sight of the the condo and seeing the spectacular view of the mountains. The condo was newly renovated, immaculate, large and each bedroom...
    Reviewed 6 April 2017
    This vacation rental is amazing! I enjoyed breakfast every morning on the deck, watching the sunlight creep across the valley and the deer grazing on the hillside. The condo...
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    About this property
    Located in beautiful Mount Bachelor Village offering spectacular views of downtown Bend & Old Mill District. This Condo House is 2.0 miles from downtown Bend and 20 miles from the slopes of Mount Bachelor Ski Resort. Nearby activities include downhill & cross-country skiing, ice skating,...
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    Bend, Central Oregon 97702
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Downtown Riverfront Cottage1 / 8
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Cable/satellite TV
    • Grill
    • Outdoor Dining Area
    • Waterfront
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 October 2016
    My wife and I stayed at the Downtown Riverfront Cottage for a week and really enjoyed our time there. Great location to everything. Walking distance to downtown and the Old Mill...
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    About this property
    This house is right on the Deschutes River. You can walk one way to town (through Drake Park), and the other way also along the river to the Old Mill District. There really isn't a better location in Bend. One bedroom with queen bed and a really comfortable queen hide-a-bed. On the Deschutes...
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    Bend, Central Oregon 97701
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    GREAT SW Bend location near Old Mill district 5 BR1 / 16
    (1)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Washer
    • Grill
    • Mountain Views
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 August 2017
    The thing that pleased me the most was the leftover and staple food in the pantry and fridge. Thanks for being so fully stocked. I also borrowed a bicycle that was in the...
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    About this property
    This home is located on the desirable, southwest side of Bend in the heart of best recreation activities that Oregon has to offer. Easy access puts Mt. Bachelor skiing, fly fishing on remote lakes, mtn. biking, rafting, kayaking or the Old Mill District & Factory Outlet shopping, just minutes away....
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    Bend, Central Oregon 97201
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    The Whispering Pine Lodge near Sunriver, OR1 / 10
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    • Mountain Views
    • Internet Access
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 August 2017
    Our stay at Whispering Pine Lodge was one of the most peaceful and relaxing vacations we have had in a long time. The Cabin was beautiful and the location was quiet. We loved...
    Reviewed 10 January 2017
    Close to Sunriver, easily able to get where you want to go. Very comfortable and well kept. Would highly recommend!
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    About this property
    *FALL/WINTER/SPRING SPECIAL* Normally $150 a night now $125 a night. 4 night minimum. Not available with any other specials or Thanksgiving weekend or Christmas Break or Spring Break. Beautiful, built in 2006, 1800+ SqFt., Luxury 3 Bedroom lodge style vacation rental located 5 minutes from...
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    Bend, Central Oregon 97707
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Classic Downtown Cottage1 / 30
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Patio
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 August 2016
    This was a perfect house for our 2 families of 4. The four kids (cousins) stayed upstairs in the loft, and the 4 adults slept downstairs. The house was very clean and we...
    Reviewed 7 June 2016
    My family (me,wife,daughter,mother,sister,brother,brother's friend) all needed a place to stay for Memorial Day. We couldn't have found a better place. Big spacious rooms. Very...
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    About this property
    The Space This house is 2 bedrooms with a secluded loft. The master bedroom has a Queen sized bed, walk in closet, and a full sized bathroom. The second bedroom has a Queen sized bed and has access to the second bathroom. Both bathrooms have custom concrete counters and tiled walk in showers. The...
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    Bend, Central Oregon 97701
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    'Scent of Pine, Sound of the Wind' Forested Remodeled Log Cabin Near Sunriver1 / 26
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 July 2017
    This newly remodeled cabin worked perfectly for 3 adults and a dog and among the best places we have rented in our 20 years of vacation rentals. It is a little off the beaten...
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    About this property
    Classic log cabin charm meets industrial vintage style. Quality natural fibers and stone are used to update this space into a cozy log cabin experience you will soon not forget. Whether listening to the wind in the pine trees or enjoying a warm real log fireplace, the feel of the big city will be...
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    Location Information
    Bend, Central Oregon 97707
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1st Street Rapids1 / 12
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cute and cozy cottage on the west side of Bend. A short stroll to First Street Rapids foot bridge and the river trail. 10 minute walk to downtown Bend with an assortment of restaurants, night life, and activities throughout the year. Convenient access to the parkway for the old mill or the...
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    Bend, Central Oregon 97701
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Updated 1BR Condo close to Mt. Bachelor1 / 14
    (3)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Air Conditioning
    • Balcony
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 July 2017
    My comments are almost identical to the reviewer from a year ago - the owner Vern was accessible and responsive, the resort was in a beautiful setting with lots of amenities...
    Reviewed 29 July 2016
    We had an excellent stay here last week. The owner was very friendly and accessible with questions. The Seventh Mountain Resort is in a great location--only a few miles from...
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    About this property
    This beautiful family vacation resort is located near Mount Bachelor, a premier Oregon ski areas and a multitude of outdoor Oregon activities, including golf, rafting, hiking, and rock climbing. Seventh Mountain Resort offers unparalleled views of the Deschutes National Forest and Mt. Bachelor and...
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    Location Information
    Bend, Central Oregon 97702
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Mountain Views
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Available All of June 2017. Call for Month Special! Great getaway spot in the heart of Bend and close to all outdoor activities Skiing, Golf, River Rafting, Hiking and more. Front Second Floor Corner Unit with the Brickhouse Restaurant downstairs. In the heart of Downtown with restaurants,...
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    Bend, Central Oregon 97703
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Wi-Fi
    • Washer
    • Terrace
    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful home has undergone a major remodel and was recently completed in the Spring of 2015. The house features a comfortable open style with panoramic windows and fabulous views of the Big Deschutes River. There is access to one of our two large decks from the living room and master bedroom...
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    Location Information
    Bend, Central Oregon 97707
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Internet Access
    • Grill
    • Cable/satellite TV
    • Patio
    • Washer
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get ready to live like a local in this gorgeous Deschutes Landing townhome with a lovely interior and great views! Located in the middle of Bend's historic Old Mill District, enjoy Bend from its very heart and leave your worries behind you. Close to everything, with access to all the urban and...
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    Bend, Central Oregon 97702
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Private loft condo - Seventh Mountain Resort1 / 2
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Balcony
    • Grill
    • Wi-Fi
    • Parking
    • Sauna
    • Hot Tub
    • Children's Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 May 2015
    This was a great place to stay when going to a show at the amphitheater. It is an older place with a few older fixtures, but very comfortable and practical. Great value. Make...
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    About this property
    Bendgetaway is a privately owned 2 bed/2 bath loft condominium located within the Seventh Mountain Resort near the town of Bend in central Oregon. Central Oregon is known for it's nearly 300 days of sunshine per year!
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    Bend, Central Oregon 97702
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Patio
    • Mountain Views
    • Washer
    • Parking
    • Wi-Fi
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Blinn’s Landing Enjoyed and cherished by family and friends since 1951, this rustic log cabin, located at the confluence of Spring River and Deschutes River, adjacent to Sunriver Resort, offers a relaxing getaway with sparkling natural springs and picturesque mountain & river views. Book now and...
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    Bend, Central Oregon 97707
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Light-filled 5BR, gameroom, hottub, ski, bike,golf1 / 31
    (4)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Mountain Views
    • DVD Player
    • Washer
    • Air Conditioning
    • Hot Tub
    • Patio
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our corner home sits on a tree-lined block within a family neighborhood with two private parks and walking paths. While Snow-capped peaks can be enjoyed from our windows, the home is conveniently located in town on the desirable Westside. It felt like home when we walked through the door of this...
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    Location Information
    Bend, Central Oregon 97701
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Beautiful SW Bend Home1 / 19
    (1)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Air Conditioning
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fantastic location in a quiet residential neighborhood, close to river trail access point, minutes from The Old Mill with lots of shopping and restaurants. An easy bike ride to the Deschutes River and downtown Bend. On site management available for anything you need during your stay, concierge...
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    Location Information
    Bend, Central Oregon 97702
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Wi-Fi
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newer home on the West side of Bend, private side yard with mature foliage. This two story home in classic West side neighborhood boasts recent furnishings, lots of natural light and easy access to the river, downtown, the Old Mill and Mt Bachelor! An open floor plan seamlessly melds the kitchen...
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    Bend, Central Oregon 97701
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A premier location at the beautiful Pioneer Park Condominiums. Located moments from the river trail that meanders along the banks of the Deschutes. You can follow this trail through to beautiful Pioneer Park; and on to the downtown core to enjoy fine music, food and unique shopping. Great choices...
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    Location Information
    Bend, Central Oregon 97701
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Porch
    • Grill
    • Parking
    • Mountain Views
    • Washer
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our 3 bedroom 2 bath house, located right near the Old Mill district, is the perfect basecamp for your adventure in Central Oregon. You'll find comfort with 2 Queen beds, 1 California King, an open kitchen & living area, a garage and a fenced yard. Our home is great for kids and pets are...
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    Location Information
    Bend, Central Oregon 97702
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Skiing: Property Is In A Ski Resort
    • Terrace
    • Washer
    • Hot Tub
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This three bedroom, two bath with reversed living offers living/kitchen spaces upstairs, a master suite with hot tub, 800 square foot deck for outdoor living, and perfect accommodations for a family or couples sharing a vacation. Enjoy easy access to the Sunriver Village plus all access passes and...
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    Location Information
    Bend, Central Oregon 97707
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a gorgeous house, newly remodeled and beautifully furnished. Located one block from the river on the West side, it's a short, charming walk to the shops, galleries and restaurants of Bend's vibrant downtown. This home has a beautifully furnished King master bedroom and full bath, a sweet...
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    Location Information
    Bend, Central Oregon 97701
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Convenient Mt. Bachelor condo w/ shared hot tub & swimming pool1 / 25
    (8)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Cable/satellite TV
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 March 2015
    Great location and also great to be near the pool, office and tennis courts and playground. We had a total of 4 people and only 3 could fit comfortably in the living room. The...
    Reviewed 28 March 2015
    As I write this review there is a noise like an audible EMP coming through the walls, which is the only time we've been bothered by neighbors, There it stopped. lovely place...
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    About this property
    Plan a snowy holiday in this one-bedroom home with a loft and luxury resort attractions at Mt. Bachelor Village. The inviting space is perfect for six guests (four adults) wishing to explore Oregon by river or mountain top! This condo is surrounded by nature. The Deschutes River Trail is outside...
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    Bend, Central Oregon 97702
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    Bunk+Brew Historic Lucas House1 / 32
    (2)Excellent
    7 Bedrooms, 2 Bathrooms, Sleeps 24 Quick View
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    • Housekeeping Included
    • Patio
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 March 2017
    From the moment you walk in, Bunk + Brew lives up to its name! Whoever checks you in, Frankie or Jay, immediately gives you a tour of the wonderful historic building and offers...
    Reviewed 23 January 2017
    This place was awesome! The owners were super friendly and knowledgeable about activities to do in Bend. The house was cozy and clean. It was 1/4 mile from downtown and 35...
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    About this property
    The Bunk+Brew Historic Lucas House is the newest and only affordable downtown destination for the adventure traveler in Bend, Oregon. 2.5 blocks from downtown shops, restaurants, and breweries, the Lucas House (1910) is Bend’s first and oldest brick building and perfect place to relax with a local...
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    Location Information
    Bend, Central Oregon 97703
    Holiday Rental House - 7 Bedrooms, 2 Bathrooms, Sleeps 24
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Grill
    • Mountain Views
    • Parking
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy Central Oregon while enjoying the authentic charm of this Old Mill home with mountain views perched above the Old Mill District. You're within biking distance to all the shops, restaurants and theater in the Old Mill District. There are three well appointed bedrooms and...
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    Location Information
    Bend, Central Oregon 97701
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Beaver Drive 165391 / 23
    (12)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    About this property
    Located 7.5 miles southwest of Sunriver, this home naturally provides the peace and quiet you have been longing for. You will enjoy the splendid hardwood floors and expansive living space with log accents. The spacious living room provides plenty of room for your friends and family to get cozy and...
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    Location Information
    Bend, Central Oregon 97707
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    Nestled in the pines, located adjacent to beautiful Pioneer Park and a short 2 block walk to downtown! This condo is part of the Pioneer Park Condos that are located along the Deschutes River. This top floor unit is perfectly situated. A lovely river trail follows the Deschutes in both directions....
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    Location Information
    Bend, Central Oregon 97701
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    About this property
    Beautiful new home on Bend's Eastside. Close to Old Mill District shopping and fine dining. Minutes to downtown and access to major arteries. Enjoy real Bend living in this lovely, well appointed, home. Granite countertops throughout. A bright gourmet kitchen has a fully equipped kitchen--complete...
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    Bend, Central Oregon 97702
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • Cable/satellite TV
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    • Mountain Views
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is 'The Shed' at the Barnyard. The Shed is where Vintage meets farm life. We have cows,hen chickens, pigs and 2 goats. It is a true farm experience. You can tour the farm or just enjoy The Shed. We are 10 minutes east of Worthy Brewing, 15 minutes from downtown Bend and the Old Mill district...
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    Location Information
    Bend, Central Oregon 97701
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    About this property
    Relax into this comfortable 3 bedroom, 2 bath home on the Westside of Bend. Only one block from the river and a charming foot bridge across to downtown Bend's vibrant restaurants and shops. Only 4 blocks to 10 Barrel and Galveston Street with easy access to Century Drive and the Mountain! The...
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    Location Information
    Bend, Central Oregon 97701
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Excellent home for a large group. A newer house with tiled floor in the living room and dining room. Kitchen has open access to the living room keeping the cook with the company and family. Unless, of course, you prefer to grill outdoors on the propane BBQ. Master bedroom has a king bed, a back...
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    Location Information
    Bend, Central Oregon 97702
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in the pines, located adjacent to beautiful Pioneer Park and a short 2 block walk to downtown. This remodeled condo is part of the Pioneer Park Condos that are located along the Deschutes River. This second floor unit is perfectly situated. A lovely river trail follows the Deschutes in both...
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    Location Information
    Bend, Central Oregon 97701
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Heyburn 3 is a newly remodeled ground floor home that is beautifully furnished and has lots of privacy. A large flat screen TV and gas fireplace in the living room adds to it's charm. The open floor plan allows for an easy flow from the kitchen to the dining area with an additional bar stool...
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    Location Information
    Bend, Central Oregon 97702
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Fantastic balcony overlooking the green space at the coveted Pioneer Park Condominiums. Moments from a trail that follows along the banks of the Deschutes River; follow it to the beautiful Pioneer Park. Only a few blocks away you can find music, food and unique shopping in downtown Bend. If you...
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    Location Information
    Bend, Central Oregon 97701
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Note: We are new to Tripadvisor so we don't have any reviews yet. However, on one of the other big booking sites we are Superhosts and have hundreds of 5 star reviews. Here's a couple of examples: Megan - March 2017 We stayed here for our 5th anniversary and it was perfect! the cottage was really...
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    Location Information
    Bend, Central Oregon 97701
    Condo/Apartment - 1 Bathroom, Sleeps 3
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Internet Access
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • Hot Tub
    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy incredible views of the Deschutes River during your stay at 'River Glen Retreat,' a 3-bedroom, 2.5-bathroom vacation rental house in Bend! The 2,500-square-foot home is located on the banks of the river and has large windows which provide guests with unbeatable vistas and also allow sunshine...
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    Location Information
    Bend, Central Oregon 97701
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Hot Tub
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    Pet friendly
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    Smoking allowed
    About this property
    Historic Delaware is vintage Bend at it's best! Next to Downtown, it's a short charming walk to Bend's vibrant shops, restaurants, art galleries and breweries. Remodeled with high ceilings and gorgeous wood floors, the kitchen is beautifully appointed. A high fenced backyard ensures privacy while...
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    Location Information
    Bend, Central Oregon 97701
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
    About this property
    Newer home in Old Mill District with back yard trail down to the river. Private backyard with mature foliage. This one story home in Elkhorn Estates boasts high vaulted ceilings, lots of natural light and easy access to the river, downtown, the Old Mill and Mt Bachelor! An open floor plan...
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    Location Information
    Bend, Central Oregon 97702
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    This newly remodeled 1 bedroom/1 bath is ideally located close to St. Charles hospital, shops and restaurants. Perfect for long term stays. Professionally decorated, fully furnished and completely stocked. Complex has beautifully maintained green spaces, dog friendly stations, picnic areas and...
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    Bend, Central Oregon 97701
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • DVD Player
    • Balcony
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The go-to destination for dining, shopping, and entertainment, the Old Mill District is within walking distance of this 3BR/2BA Bend house. A mix of old and new, the district offers boutique shops, art galleries, restaurants, amphitheater, and even a fly fishing course. When the weather’s warm, try...
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    Location Information
    Bend, Central Oregon 97702
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
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    About this property
    Available as a monthly rental, this beautiful 3 bed/2.5 bath home has high ceilings with sky lights for great lighting throughout the grand entrance. Enjoy sitting outdoors with plenty of seating around the fireplace and bbq. This home has a spacious office room on the first floor with surrounding...
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    Location Information
    Bend, Central Oregon 97701
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Osprey open and bright! Right across from Tethrow and Phils Trail, wow!1 / 32
    (12)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Grill
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    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The perfect large family home that makes you all feel at home. Situated in one of the nicer west side neighborhoods, you will find the Osprey. Right by Phil's Trail and Tetherow is across the street, and just up the street is Widgi Golf course and spa. A hiking trail to downtown is just steps away....
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    Bend, Central Oregon 97702
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This newly remodeled 1 bedroom/1 bath is ideally located close to St. Charles hospital, shops and restaurants. Perfect for long term stays. Professionally decorated, fully furnished and completely stocked. Complex has beautifully maintained green spaces, dog friendly stations, picnic areas and...
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    Bend, Central Oregon 97701
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1
    Bend Holiday Rentals

    Surrounded by the stunning snowcapped peaks of the Cascade Mountains and the largest juniper forest in the western U.S., Bend is an outdoor recreation enthusiast’s paradise. Known for its cycling, hiking, kayaking, fishing and golfing, Bend, in the central part of the state, gets your adrenaline flowing in a variety of ways.

    Following a full day of intense activities, you’ll need a comfortable place to relax and recharge. Consider a spacious holiday rental where you can spread out and prepare your own meals rather than small hotel room. Whether you want to stay near downtown, in the Old Mill District, or near the Mt Bachelor ski resort, we have lots of villas, multi-bedroom homes, cabins, condos and other choices that are a better value than a hotel.

    Bend attractions and activities

    Bend is a phenomenal outdoor environment to leave the computers and televisions behind for a few hours or days. Family activities abound starting with the Lava Lands Visitors Center, about 15 minutes from downtown, where you’ll see the Lava Butte, a 7,000-year-old cinder cone lava formation that rises 500 feet. For thrill seekers, raft or kayak the white waters of the Deschutes River, take a panoramic chairlift ride up Mt. Bachelor, hike along Tumalo Creek or fish for trout at a well-stocked pond at Shevlin Park.

    Golfers have ten picturesque and challenging golf courses to play in the Bend area, including the Jack Nicklaus designed Pronghorn Golf Club, Crosswater at Sunriver Resort, a Bob Cupp design, and the affordable, family-owned Aspen Lakes Golf Club, where you’ll find lots of local residents.

    Downtown Bend is brimming with shops, galleries, restaurants, microbreweries and bars, which will enhance your visit to this former logging town.

    Holiday rentals for families

    From rustic cabins and cozy cottages to amenity-loaded condos and holiday homes with high-speed Internet, swimming pools, fireplaces and hot tubs, we can provide you with an extensive list of options in Bend. A great money-saving feature in all holiday rentals is the fully equipped kitchen, which allows you to provide delicious meals and snacks for your family instead of dining at pricey restaurants that’ll quickly destroy your budget.

    Deals on Bend holiday rentals

    When you visit Bend, your goal is to free your mind in the wondrous natural surroundings and the last thing you want to do is anguish about how much you paid for a cramped hotel room. Holiday rentals are a great value and we have special deals and discounts on a wide variety of properties in different areas of Bend in every price range.

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