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Sisters Holiday Rentals

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    Travellers to Sisters are booking November dates now. Secure your holiday rental today, and have the perfect trip.
    All 66 Rentals in Sisters
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    Spacious, dog-friendly home w/ a deck & gas grill - near Whychus Creek!1 / 26
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Rustic cabin w/ shared pool, tennis & adventure nearby!1 / 24
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Spacious, secluded home w/ private hot tub & mountain views - dogs welcome!1 / 28
    (1)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Peaceful five-acre retreat w/ private hot tub & wood fireplace, close to golf1 / 42
    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Say hello to a relaxing, laid-back Central Oregon getaway when you stay at this secluded Sisters vacation rental. Nestled on five acres just outside the city limits, this home boasts a private hot tub and a wood-burning fireplace in addition to convenient amenities such as a washer and dryer....
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    Sisters, Central Oregon 97759
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 13
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    Spacious, highly unique home w/ shared pool, tennis, borders the forest!1 / 34
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    • Sauna
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're looking for a peaceful Central Oregon getaway to share with your large group, consider staying at this stunning Sisters vacation rental. Custom built by an architect with experience designing churches, this cathedral-esque home boasts five bedrooms, a loft, a private washer/dryer, free...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Quiet dog-friendly studio with cable, jetted tub, wood stove - panoramic views!1 / 26
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
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    • Mountain Views
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    Pet friendly
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    About this property
    Escape the hustle and bustle of daily life when you stay at this charming, dog-friendly studio. Enjoy the peace and quiet of the incredible Central Oregon landscape while you reconnect with your loved one and spend time exploring the beautiful natural surroundings. Situated in the countryside 10...
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    Sisters, Central Oregon 97701
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Family-friendly house with a private hot tub & 30 acres of land!1 / 45
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Plan a rejuvenating trip to Central Oregon at Sisters Mountain View Ranch, where you'll find 30 acres of private land and a private hot tub for a family of up to nine to have a great time! Located a few miles south of downtown Sisters, you'll enjoy privacy while still having conveniences close at...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    Convenient, refurbished, picturesque cottage near trails and the center of town1 / 24
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming 1930's-era bungalow in the heart of historic Sisters offers a comfortable and convenient way to enjoy a romantic or adventure-packed vacation in the Cascades. Set on a quiet street within walking distance to restaurants, coffee shops, galleries and the theater downtown, this Central...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Charming, family-friendly house w/ separate studio in downtown Sisters!1 / 32
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take a trip to Sisters and enjoy a stay at this charming house right in downtown. With entertainment, a central location, and a separate studio for privacy, up to six guests will have a great time here! Located across from the Village Green City Park just a couple blocks from the main street in...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cute cabin with wonderful community amenities - including a shared pool!1 / 28
    (1)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Cute Cabin Convenient to Sisters
    Reviewed 12 January 2016
    This place was perfect as a home base for snow activities in Sisters. It is located about a mile out of town and about 20 minutes from the Three Creeks Snow Park. Cabin had...
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    About this property
    Hole up in this cheerful Sisters vacation cabin for some quality time with your favorite people. Surrounded by trees and an enclosed backyard and with access to shared amenities like a pool and tennis courts, this rental gives you the best of both worlds! In the Tollgate community three miles from...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Modern, riverfront home w/ entertainment in a quiet, charming community1 / 43
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This comfortable, riverfront home in Sister, OR is the perfect spot for your next getaway! Up to eight guests will feel at home here with modern furnishings and access to the Wychus Creek right out the back door. Located in a quiet neighborhood in downtown Sisters, you'll be able to enjoy peace...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cozy cabin w/resort attractions like shared pool + private hot tub & fenced yard1 / 24
    (3)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    great house
    Reviewed 6 August 2015
    I brought family traveling from outside the U.S. and they loved this house . Great sleeping options with the bunk beds . Loved the hot tub !!! Very cozy with wood interiors...
    Cute Cabin
    Reviewed 4 August 2014
    This was our first trip to central Oregon for a ladies get away. The cabin was very cute but upon check in , realized that the cabin only had a old heating/cooling system so it...
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    About this property
    Sisters Tollgate Cabin is nestled among the pine trees on the edge Deschutes National Forest. Knotty pine walls and western decor provide rustic ambience in this two bedroom vacation cabin. Downtown Sisters is just three miles away, where art, culture, and dining abound. Premier mountain biking,...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cozy cabin w/ shared pool, tennis courts, near town & wilderness1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This rustic cabin in Sisters, OR offers access to a shared pool, tennis courts, and proximity to wilderness and conveniences for up to eight guests to feel at home! Sitting in the quiet and relaxed Tollgate community three miles outside of Sisters, a quick drive will bring you to the charming...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Golf Home 0261 / 8
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
    • Shared Indoor Pool
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    Pet friendly
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    Smoking allowed
    About this property
    Spacious family-friendly home located on the 16th fairway of Big Meadow Golf Course. Large open kitchen with granite countertops and bar seating. The dining area adjoins the Great Room where you can dine, play cards or games, or lounge in front of the fireplace. Two bedrooms with King and Queen...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Premier Black Butte Golf Home **w/ Hot Tub & Sauna**1 / 24
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Quick Summary: 5 bed + den, 4 bath 4000 sq ft sleeps 12-14 wifi internet access located on the 15th hole of Big Meadow Golf Course **includes hot tub and sauna** This premiere 5 bedroom plus den, 4 bathroom 4000 sq ft home on the 15th fairway of the Big Meadow Golf Course is a...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    Family Oriented Cabin At Black Butte Ranch1 / 23
    (5)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Patio
    • Satellite TV
    • Shared Indoor Pool
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    Pet friendly
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    Smoking allowed
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Beautiful Black Butte Ranch Home With Amazing Location1 / 10
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Patio
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Stylish Bend Mountain View Home1 / 20
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Internet Access
    • DVD Player
    • Central Heating
    • Satellite TV
    • Balcony
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Sisters, Central Oregon 97701
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Spacious Cabin In the Pines1 / 23
    (6)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
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    Pet friendly
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    Sisters, Central Oregon 97759
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Great Home for Quilt Show Week1 / 13
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Washer
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    Pet friendly
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    Wonderful!
    Reviewed 16 July 2015
    Ryan was excellent to work with and very thoughtful! We're looking forward to staying in his lovely home again next year!
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    About this property
    Serious Quilters will love this house and location!! We have a 2500 Square feet home with 4 bedrooms and a home office (that easily converts to a 5th bedroom). We can sleep 9 on beds and another 4 on air mattresses. $350/night with a minimum of 4 nights. Great outdoor living area in the...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    East Meadow 0511 / 16
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Large 5 bedroom 4 bath home with an additional family room/6th bedroom with pullout sofa sleeper. Most of the home is on the main floor with the 5th bedroom and family room above the garage. You have 2 living rooms, large kitchen/dining room, and a spacious deck that backs up to the forest service...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    Peaceful mountain views, pet-friendly home with easy access to Sisters and Bend1 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sisters, Central Oregon 97701
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Most Desired Mountain View And Setting In Sisters Oregon!1 / 26
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Internet Access
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    You can't beat this practically new home on the west side of Pine Meadow Village. A corner lot with an awesome view of Three Sisters. Relax on our large covered porch and watch the mountains, sunset, and roaming deer. Or just relax in our living room and view it all out of two sets of glass...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    A private hot tub, shared pool, & National Forest at your backdoor await1 / 36
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    This comfortable vacation rental in Sisters is a fantastic place to plan your next Central Oregon adventure. Nestled in Tollgate, an authentic western-style community, when you stay here you will have easy access to city businesses, shared amenities such as a pool, plus your very own private hot...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Black Butte Getaway Golf Home 2811 / 23
    (21)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Spring Specials! Walk or ride bikes to play at the Glaze Meadow Pool!1 / 16
    (19)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 12
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    June 27th - July 1 available1 / 24
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Satellite TV
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    Sisters, Central Oregon 97759
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    Beautiful 3BR, 2.5BA w/Pool & Jacuzzi. Located in Sisters!1 / 24
    (6)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Private Outdoor Pool (Unheated)
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    Sisters, Central Oregon 97701
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 BR Home, 1 Block to Glaze Meadow Rec Complex, Hot Tub1 / 12
    (12)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    Pet friendly
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Most Desired Mountain View Setting In Sisters! Clubhouse Pool, Central Air1 / 24
    (34)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Beautiful upstairs townhouse in the heart of Sisters1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Terrace
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Fantastic location by Paulina Springs - close to tennis, pools, golf & meadow1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Sauna
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    • Hot Tub
    • Housekeeping Included
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    Pet friendly
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Spacious Craftsman Beauty in Sisters!1 / 24
    (34)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Updated Black Butte house with 2 master suites. Great for 2 families.1 / 24
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Sisters, Central Oregon 97759
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Custom spacious home on one acre of pines will accomodate large group1 / 24
    (20)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
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    Sisters, Central Oregon 97759
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Perfectly Located Black Butte Home Sleeps 101 / 24
    (5)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
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    Pet friendly
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    Sisters, Central Oregon 97759
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Country Retreat with plenty of room to relax or play!!1 / 21
    (12)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Sisters, Central Oregon 97759
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    Beautiful Home Just Steps From Pool, Tennis Courts And Bike Paths!1 / 18
    (18)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1- Level Cottage, Shops 2-Blks, Pine Meadows, Swim/HTub, Cozy, Clean & Cute1 / 24
    (59)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Sisters, Central Oregon 97759
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Soaring Windows, Abundant Light -- book for Summer 20181 / 24
    (8)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Aug. 26th & 27th Special - In the Heart of Downtown, Quiet, Sisters View/Swim/HT1 / 24
    (26)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sisters, Central Oregon 97759
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    ~Newly Renovated~High Desert Comfort~1 / 24
    (2)Poor
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Stunning Cascade Views and Glorious Sunsets1 / 17
    (30)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Sisters, Central Oregon 97701
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Enjoy Our Dog/Family Friendly House In Tollgate1 / 24
    (32)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedroom Ranch House on 10 Acres Just Outside Sisters Township.1 / 13
    (23)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Just opened bookings for Summer 2018!1 / 22
    (15)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Sisters, Central Oregon 97759
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Beautiful Setting, large lot w/ view of 16th fairway, Private Hot Tub!1 / 24
    (18)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Sisters, Central Oregon 97759
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Sleeps 5 Families Comfortably; National Forest, Pool, Tennis Is Your Backyard1 / 24
    (13)Very good
    7 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    Sisters, Central Oregon 97759
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 20
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    Location, location, location!1 / 19
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    Perfect Black Butte Ranch Getaway1 / 19
    (20)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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