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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 186 Rentals in Bend
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    8 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    3 Mt Baker1 / 30
    (1)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Mt Bachelor Village -Top floor with 2 Queen beds +1 / 22
    (7)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 5 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Located just 3 miles South of Sunriver Resort, this charming log cabin is located on the access canal just a few paddles in from the Deschutes River. Get away or get together at this inviting mountain retreat located approx. 4 miles Southwest of Sunriver. Experience exceptional outdoor living on...
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    Bend, Central Oregon 97707
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Second Street Cottage-convenient yet secluded downtown Bend retreat1 / 27
    (69)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Cable/satellite TV
    • Grill
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    • Mountain Views
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 September 2018
    Great location, sparkling clean cottage, beautiful gardens, welcoming host - this place is truly special
    Reviewed 30 August 2018
    My wife and I just returned from a 2 week long Oregon vacation. We spent the first week at the Second Street Cottage in Bend and we loved it! The Cottage is immaculately clean...
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    About this property
    Secluded and quite 1 bedroom cottage just a 4 minute walk across Newport Ave bridge to numerous activities and businesses in downtown Bend. ~Immaculate, professionally decorated Cottage. ~Large Bathroom with deep tub, tiled walls and multiple shower heads. Tankless water heater provides all the...
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    Bend, Central Oregon 97703
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    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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    Bend, Central Oregon 97707
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Cozy&Upscale Vacation Rental in Beautiful Bend offers 3 bedrooms, 2.5 baths1 / 19
    (16)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Patio
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    • Wi-Fi
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2014
    It was very beautiful house! 5 mins from old mill district and 3mins from wal-mart by a car. It has everything you need to stay. Back yard was fenced so nobody can see inside...
    Reviewed 9 July 2014
    Situated in a SW neighborhood of Bend, OR, this house is only a 5 minutes drive from Old Mill and downtown. We biked there and back, winding through the neighborhoods, as the...
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    About this property
    Artist from Bay area offers your stay in a delightful home in SW Bend. Original art from the owner and photography from all around the world, grace the walls. 3 bedrooms, 2.5 bathrooms sleeps 6 comfortably , 1750 sq.ft. King master suite, and queen bed in second bedroom with private bathroom and...
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    Bend, Central Oregon 97702
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    About this property
    Private Retreat for Two!  Great Westside Location, Newly Furnished One of our newly remodeled, and beautifully furnished Bend, Oregon vacation home rentals, Galveston Studio is an upstairs apartment that is private and quiet.  Perfectly situated on the west side - a short walk to 10 Barrel,...
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    Bend, Central Oregon 97701
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Stroll the River or downtown from this Condo- In the heart of Bend1 / 15
    (6)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 September 2018
    We stayed 3 nights mid September. Apartment unit clean, well stocked. 2nd full bath very convenient for those morning departures to see the area’s treasures. Location of the...
    Reviewed 16 February 2018
    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...
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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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    Tumalo Pines1 / 18
    (11)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Central Heating
    • Mountain Views
    • Hot Tub
    • Washer
    • Cable/satellite TV
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    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 July 2018
    We have totally enjoyed our stays at Tumalo Pines. It is peaceful and relaxing and quiet. The home is spacious, comfortable, and nicely clean. We have been there now 4 or 5...
    Reviewed 29 November 2016
    This house was beyond perfect for our 2 families (4 adults & 3 kids). It's remote but not too remote, and you feel instant serenity upon arrival. We had a blast wandering...
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    About this property
    Private country setting with mountain views just 5 miles northwest of Bend. This 12 year old home sits on 20 acres of open juniper and pine forest, surrounded by other large, open tracks of land. The setting is lovely and private - like your own, private park with a house in the middle of it!...
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    Bend, Central Oregon 97701
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    7th Mountain Resort in Bend, Or1 / 21
    (3)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 24 June 2018
    Very comfortable lodging. The condo owner was very responsive to a small issue.The children enjoyed the pool and miniature golf.
    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...
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Mountain Views
    • Grill
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The home is located in a quiet and peaceful setting, just minutes from all the great entertainment and restaurants to be found in downtown Bend. If you like great beer, you are in the right place. At last count, there were 31 micro breweries in town. Spring is a great time to be in the house....
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    Bend, Central Oregon 97702
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Mt.Bachelor Village Resort--Comfortable living1 / 14
    (8)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 24 February 2018
    If you want privacy and roominess close to skiing and just outside Bend, this the place. Some variation in the units but same basic amenities. Updates must be on a rotation...
    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...
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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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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home has been remodeled and nicely furnished. It is ready for your relaxing adventure in Bend. Over-stuffed couches frame the living room in comfort and style. The extra large dining room is perfect for socializing and family style meals. The country kitchen is well appointed. An extra...
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    Bend, Central Oregon 97701
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Stay near beautiful Downtown Bend in one of the nicest Bend, Oregon vacation home rentals, the Albany House! This recently renovated cottage is a well-furnished 3 bedroom, 2 bath home, located in a charming residential neighborhood only minutes from Downtown Bend and the Old Mill District. Albany...
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    Bend, Central Oregon 97702
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
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    Pet friendly
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    About this property
    This single level home in the SE end of Bend is at the end of a cul de sac and has been newly decorated with tasteful decor. It's a quick walk to Ponderosa Park, Larkspur trail, and Pilot Butte, allowing for easy access to Bend living. Adjacent to Pilot Butte Airstrip, making this a unique spot to...
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    Bend, Central Oregon 97702
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Luxury and Comfort at Mount Bachelor Village Condo, Views, Mountains and Lakes!1 / 42
    (7)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
    Reviewed 10 October 2018
    The condo was all updated and absolutely gorgeous! It came stocked with all the essentials needed during our stay. We found ourselves wanting to just stay in the condo and relax...
    Reviewed 29 June 2018
    This is a great location to relax and escape the everyday hustle. It was great to have a big enough space to enjoy the family,cooking and playing together. The grand-kids loved...
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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 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Washer
    • Cable/satellite TV
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    • Mountain Views
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Property From the ski slopes of Mt. Bachelor to the raging water of the Deschutes, the outdoor capital of the world beckons from the luxury stylings of 'The Ponderosa Loft' at The Mount Bachelor Village Resort. Surrounded by the beauty of central Oregon, this newly remodeled 2 bedroom – 2 bath...
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    Bend, Central Oregon 97702
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    5 Bedrooms, 5 Bathrooms, Sleeps 13 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    Cairn is our brand new, absolutely perfect, luxurious, rental home at Tetherow in Bend, Oregon. If you're expecting only the best, then this house will not disappoint. This 5 bed, 5 Bath, super modern home has plenty of room for the whole family. Situated among elegant and earthy surroundings, you...
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    Bend, Central Oregon 97702
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 13
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    Three Rivers Retreat near Sunriver1 / 22
    (4)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 July 2018
    The house had great river access. You can play in the tributary or get out on the river and float to the dock. We kayaked to the dock probably 3-4 times a day. Great selection...
    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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Comfortable and cozy 'Mirror Pond' sits on the banks of the Deschutes River at Mirror Pond and Drake Park in the heart of downtown. It is located in one of the most picturesque locations in Bend. This home is one of few Bend, Oregon vacation rentals that has both a mountain cabin and cottage feel...
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    Bend, Central Oregon 97701
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Shevlin Trail1 / 24
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
    Reviewed 2 weeks ago
    Great home, immaculate, kitchen had everything you could need. Comfortably accommodated our party of 8 adults. We enjoyed some trail runs on the Shevlin/Tumalo network. I've...
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    About this property
    Relax in front of the stone, wood-burning fireplace on a chilly evening, and enjoy the spacious open living, dining and kitchen area. This four-bedroom home has all the comforts you are looking for, and plenty of space for couples or a family to share. There is seating for six at the heavy, wooden...
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    Bend, Central Oregon 97701
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Cumberland is one of the most perfect Bend Oregon rentals to vacation in! This updated 3 bedroom, 2 bath home is located right in the heart of Northwest Bend - a family friendly neighborhood! Walking distance to breweries, restaurants, shopping, and more! This is the perfect house to come to after...
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    Bend, Central Oregon 97703
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New Listing! Rimrock . . . open, light and bright Bend rental that will have you feeling like you are in a first class tree house. This renovated West Hills home is just minutes from everything. Views of the Paulinas from the living area and the Cascades from the upstairs master bedroom. Great...
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    Bend, Central Oregon 97703
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    One of the most conveniently-located Bend, Oregon vacation rentals on the much sought after west side, Wild Rye sits on a secluded 1 acre lot in a beautiful, private community! With easy access to all that Bend and Central Oregon has to offer, you'll find yourself minutes away from hiking and...
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    Bend, Central Oregon 97701
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
    About this property
    One of the coolest Bend rentals to vacation in, Hill Top is a deluxe four-bedroom home on the south side of Awbrey Butte, on Bend's west side. Located in a quiet hillside neighborhood about ten blocks from Downtown Bend, it is within walking distance or a short bike ride to the Deschutes River at...
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    Bend, Central Oregon 97702
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    About this property
    Located in the heart of Sunriver, this pleasant 2 level 1600+/- sq. ft. condo is just a short stroll to the SHARC, Meadows Golf Course and the Sunriver Village Mall. The resort area has a number of activities available including over 30 miles of bike paths, world class golf courses, swimming,...
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    Bend, Central Oregon 97707
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    About this property
    Stunning property in Sunriver surrounded by high-end homes, yet a short walk or bike ride to the river, Village and Aquatics Center. This luxurious vacation home is full of light with large windows. Truly a spot for all of your guests with 6 bedrooms, 4 of which are master suites. This home sleeps...
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    Bend, Central Oregon 97707
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 16
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    West Bend Luxury 3 BR 3 Bath Townhome - The Bluffs neighborhood of the Old Mill District. Close to Downtown, Mt Bachelor & Deschutes. Among the largest Bend, Oregon vacation rentals we offer, The Oasis is a 1,763 square-foot, luxury three-bedroom and three-bathroom townhome located in the Old Mill...
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    Location Information
    Bend, Central Oregon 97702
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Outlaws & Angels Horse Ranch1 / 22
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Private Garden
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    Pet friendly
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    Smoking allowed
    Reviewed 9 July 2018
    This was so awesome and we sure did have a good time. Staying here was a wise choice for we were extremely happy with everything. This is a warm and cozy place to stay for...
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    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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    Location Information
    Bend, Central Oregon 97701
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    About this property
    Gorgeous, new, luxury vacation home nestled in the trees on Bend's west side, along Century Drive, on the road to Mt Bachelor and steps from Tetherow. Room for the entire family in this new luxury home, plus attached guest quarters with 2 of the bedrooms, additional living space and kichenette, for...
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    Location Information
    Bend, Central Oregon 97702
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Downtown Riverfront Cottage1 / 8
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    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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    Location Information
    Bend, Central Oregon 97701
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    About this property
    Aspen Ridge is one of the quaintest Bend, OR vacation homes around! This tranquil 3 bedroom, 2.5 bath home located in a quiet neighborhood surrounded by Ponderosa Pines, just 2.5 miles from The Old Mill. With close neighborhood access to the Deschutes River Trail, and recent updates, Aspen Ridge is...
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    Bend, Central Oregon 97702
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    About this property
    Looking for one of the most modern Bend, Oregon vacation home rentals around? And with a convenient location near both outdoor recreation as well as the comforts of town? Urban Roundabout is a newly built, northwest contemporary home within walking distance to Newport Market, local restaurants,...
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    Bend, Central Oregon 97702
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    About this property
    ** 6 Month Minimum - Gorgeous end unit situated on the 18th hole of Widgi Creek Golf Course this home features wonderful views of the fountain. Beautiful hardwood flooring throughout most of the main floor and slab granite counters in the kitchen are just a couple of the recent renovations. Smart...
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    Bend, Central Oregon 97702
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    River View!! Overlooking the Big Deschutes River this spacious home located approximately 7 miles south of Sunriver is your key to a relaxing vacation. Launch your canoe or kayak right from the back yard and enjoy a quiet, serene float or fish from a lawn chair and enjoy the view. The great room...
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    Bend, Central Oregon 97707
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    One of the nicest Bend, Oregon vacation rentals around, Canal View, is a beautiful home located on the canal near the Old Mill District. This four-bedroom home features airy, open living spaces inside, and landscape lighting, a stone patio, season water feature and natural gas fire pit outside. The...
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    Bend, Central Oregon 97702
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    26 Yellow Pine is a great place to call home while visiting Sunriver. This home easily accommodates 10 comfortably. This is a 4 bedroom, 3 bathroom home, that is fully stocked with anything you may need in your home away from home. Beds in this home are as follows: 1 king bed, 2 queen beds, 3 twin...
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    Bend, Central Oregon 97707
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Of all the Bend, Oregon rentals to vacation in, River Ridge 617, is certainly one to see all the sights. Enjoy the impressive views of the Deschutes River, as well as the amenities of Mt. Bachelor Village Resort, including a swimming pool and more. This three-bedroom, second floor condominium has...
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    Bend, Central Oregon 97702
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
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    • Private Outdoor Pool (Heated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One of the nicest Bend vacation rentals around, Big Pine, is a fantastic 3 Bedroom, 2.5 Bath house, located in the River Wild neighborhood in Mount Bachelor Village. This open concept home has an abundance of light and features 2 master king suites, and a 3rd double queen room to accommodate the...
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    Bend, Central Oregon 97702
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    About this property
    If you are looking for a wonderful home away from home, Modern Grace is the place for you! This new and absolutely stunning home has a 30 day minimum, perfect for long term lodging. This new home is fully equipped with everything you need, and is perfectly located in NW Bend between COCC, OSU,...
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    Bend, Central Oregon 97701
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    About this property
    One of the nicest Bend, OR vacation home rentals,Vantage Point, is located just a short 3 minute walk from the Old Mill, Deschutes River, Restaurants, Shopping, Festivals and Concerts. This elegant and peaceful home is newly decorated and comfortable for the entire family. This exquisite 1800...
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    Bend, Central Oregon 97702
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home, one of our most popular Bend, Oregon vacation home rentals, has a view that will take your breath away. You'll feel the tension leave the moment you walk in the front door. Enjoy majestic sunrises in the mornings while sipping a cup of freshly brewed coffee. On a clear day view the...
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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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    About this property
    Absolutely the best location in Bend! In the heart of downtown - just steps to cozy, hidden fire pits and food, live bands and brews, art and charm. The Downtowner Apartment is a fantastic 2 bedroom/1 bath upstairs hideaway. Surrounded by all that downtown Bend has to offer, this loft style...
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    Bend, Central Oregon 97701
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Smoking allowed
    About this property
    3 Tumalo is a beautifully renovated home featuring 4 bedrooms. The perfect light & bright floor plan w/wood burning stone fireplace in the vaulted great room. The kitchen has been updated with granite tile counter tops, wood flooring and is fully stocked with all the amenities you will need while...
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    Bend, Central Oregon 97707
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Kid friendly
    Smoking allowed
    About this property
    8 Deschutes Lane is located just a quiet .75 mile walk or bike ride from the the Sunriver Village. Nestled in the quiet south end of Sunriver, just steps from the Deschutes River, is your cozy Sunriver Retreat. If you love Kayaking, SUP, or just floating the river, you will love this location at...
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    Bend, Central Oregon 97707
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Enjoy the luxury of a private, gated golf community in this beautifully-furnished townhome. Villa #6 is a two-bedroom, two-bath townhouse located in the quiet community of Broken Top. Enjoy beautiful views of the 18th Fairway of the privately-operated Broken Top Golf Course from the living room and...
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    Bend, Central Oregon 97702
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
    About this property
    Stay in style at Mt. Bachelor Village, home to some of the nicest vacation rentals in Bend, Oregon, and just a short drive or walk from Old Mill District!  This unit is great for one large family or two small families traveling together, and can be combined with our Big Pine property for larger...
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    Bend, Central Oregon 97702
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    • Private Outdoor Pool (Heated)
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    • Mountain Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're looking for the best of Bend's luxury vacation rentals, Outcast is an ideal choice. Named for one of the owner's favorite craft beers at Crux Fermentation Project, Outcast is the perfect balance of down-to-earth attitude and elegant luxury. Located in the far-Westside neighborhood of...
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    Bend, Central Oregon 97702
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    About this property
    This new, custom built log home, located just eight minutes from the resort community of Sunriver, and 25 minutes from Mt. Bachelor Ski Area, provides and ideal 'base camp' for access to skiing, snowmobiling, sledding, hiking, mountain biking, fishing (right from the back yard!), restaurants,...
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    Bend, Central Oregon 97707
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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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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