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Sisters Holiday Rentals

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    Travellers to Sisters are booking March dates now. Secure your holiday rental today, and have the perfect trip.
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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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    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Quiet dog-friendly studio with cable, jetted tub, wood stove - panoramic views!1 / 26
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    • Sauna
    Suitability
    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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    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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    Rustic cabin w/ shared pool, tennis & adventure nearby!1 / 24
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Balcony
    • Parking
    • DVD Player
    • Grill
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 June 2017
    We enjoyed our stay in this authentic log cabin. Loved the decor, comfy beds andpersonal touches. Great location to Sisters and fishing, hiking and biking.Had a fire each...
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    About this property
    This traditional log cabin in Sisters, OR will accommodate up to seven travelers to enjoy modern amenities, a shared pool, and tennis courts! Part of the Tollgate community just three miles from the heart of Sisters, you'll enjoy bike paths and easy access to outdoor fun. With a cozy, rustic...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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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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    • Patio
    • Internet Access
    • Cable/satellite TV
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    • Mountain Views
    • Washer
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2017
    You could not ask for a more picturesque landscape. The mountains, and the stars were breathtaking. Spacious and comfortable. Lots of dishes and games. Close to Sisters...
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    About this property
    If you're planning a Central Oregon getaway, you can't go wrong with a stay at this dog-friendly Bend vacation rental. Whether you're lounging on the spacious decks, admiring the mountain views as you soak in the private hot tub, or relaxing in front of the wood stove, you and your loved ones are...
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    Sisters, Central Oregon 97703
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Hot Tub
    • Grill
    • Waterfront
    • Cable/satellite TV
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    • Washer
    Suitability
    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, access to the Wychus Creek right out the back door, and your own private hot tub. Located in a quiet neighborhood in downtown Sisters, you'll...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
    • Mountain Views
    • Cable/satellite TV
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    • Air Conditioning
    • Hot Tub
    • Grill
    • Washer
    Suitability
    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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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    • Mountain Views
    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Retreat to this large, spacious home in Sisters with your family and friends - plus the family dog! You'll have plenty of room to relax, a lovely deck with a gas grill, and a great location near town and lots of outdoor recreation. Located in the quiet Squaw Creek community of Sisters, this home is...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    • Internet Access
    • Cable/satellite TV
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    • Balcony
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    • Hot Tub
    • Washer
    • DVD Player
    Suitability
    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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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • DVD Player
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    Suitability
    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
    • Air Conditioning
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    • Patio
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    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
    • Hot Tub
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Internet Access
    • Air Conditioning
    • Hot Tub
    • Washer
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    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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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Shared Indoor Pool
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    Pet friendly
    Kid friendly
    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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    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    About this property
    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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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Washer
    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    • Patio
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 5BR/4BA home offers a private, woodsy stay at Black Butte Ranch, where you can spend your days reading on the wraparound deck, exploring the trails, or making new friends at the horse stable. The Lodge, with indoor pool and rec center, is just a few miles away. Your 3,000 sq. ft. retreat...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your home away from home, attention to detail you`ll appreciate. Located in a quiet neighborhood, wonderful yard with soothing water feature and hot tub that will help you unwind. Landscaped yard You will likely see deer meandering thru the yard everyday. The homeowners have gone the extra mile...
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    Sisters, Central Oregon 97759
    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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    About this property
    You will love this new family friendly home with modern furnishings and air conditioning. Complete with a covered outside patio area that includes a propane BBQ, hot tub, and nice, comfy outdoor furniture to enjoy your vacation evenings! Stargaze amongst large ponderosa pines while relaxing in the...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Smoking allowed
    About this property
    Welcome to the historic Fish Inn Bike Inn, originally built as the Sisters Ranger Station in 1935, it has been lovingly & beautifully restored as a premier vacation home in Sisters, Oregon. Winner of the 2013 DeMuro Award from the Restore Oregon for Excellence in Preservation, Reuse and Community...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Room for your whole family in this beautiful spacious home in a great location for your family vacation, just minutes from downtown Sisters. Come and make memories with your loved ones! Free pool access at the Tollgate seasonal pool, biking paths all around the community, a tennis court, basketball...
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    Sisters, Central Oregon 97759
    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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    Pet friendly
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    Smoking allowed
    About this property
    Beautiful custom built condo on ground level in desirable Pine Meadow Village with exceptional outdoor space. Spacious, 1720 sq. ft. of living space, the clubhouse, with seasonal swimming pool and year round spa, is conveniently just across the street from this very spacious property. Walking...
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    Sisters, Central Oregon 97759
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Great affordable vacation home for 2 couples or a small family, 2 bedrooms, 2 bathrooms, will sleep up to 6. Free pool access at the Tollgate seasonal pool, biking paths all around the community, a tennis court, basketball court and many acres of National Forest land for miles of mountain biking or...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    • Terrace
    • Parking
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Park the car and walk or bike to everything in town, mountain views and A/C. Come to Sisters and take in the views of four mountains and pond w/seasonal fountain from this condo. It is on the west edge of Sisters and only a few blocks to the heart of downtown Sisters to shop, dine, browse. Year...
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    Sisters, Central Oregon 97759
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    Pet friendly
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    About this property
    Time for a romantic getaway? Whispering Canyon is the perfect spot. Craving some sunlight? South facing wall of windows fills the cabin with warm sunny light. Watch the sunrise over the canyon and set over the mountains, quiet, peaceful, relax, stargaze. Located 7 miles NE of Sisters Oregon, this...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Sisters Suite - South is one of three brand new lodging offerings next to Pine Meadow Village in Sisters Oregon. Available this summer and fall for nightly and weekly rentals and in the fall it will be available for month to month rentals. New and modern, all you need for comfortable lodging...
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    Sisters, Central Oregon 97759
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This winning 3BR/3BA vacation home is nestled in the pine trees on a half-acre lot in beautiful Black Butte Ranch. With three sitting areas, a cozy gas fireplace, sleeping loft, and an expansive wraparound deck, there’s plenty of room for up to seven guests to gather comfortably. Experience one...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Inviting and sunny, the wall of windows and vaulted ceilings make this condo a delight to be in, in the quaint Pine Meadow Village neighborhood. Enjoy everything Sisters has to offer, walk to everything in town, hang out at the pool (seasonal), or soak in the hot tub. There are tennis courts just a...
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    Sisters, Central Oregon 97759
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Pet friendly
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    About this property
    New and modern, bright and cheery, all you need for comfortable lodging without sacrificing all the creature comforts. Come enjoy this air conditioned one bedroom, one bath condo next to Pine Meadow Village. Mountain Views from the bedroom. This condo features a king size bed and full size aero...
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    Sisters, Central Oregon 97759
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Pet friendly
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    Smoking allowed
    About this property
    New and modern, comfy and efficient, all you need for comfortable lodging without sacrificing all the creature comforts. Come enjoy this air  conditioned one bedroom, one bath condo next to Pine Meadow Village. Mountain Views from the bedroom. ADA Side Approach Design in the kitchen, and features...
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    Sisters, Central Oregon 97759
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    You'll feel like you're a world away, while being within walking or biking distance to downtown Sisters. Just minutes to shops and restaurants, cozy Meadow View Cabin offers peace and quiet on 10 acres with sage, junipers and towering pines. The Cabin overlooks 60 acres of natural meadow bordered...
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    Sisters, Central Oregon 97759
    Cabin Holiday Rental - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Spacious home with upstairs loft In the heart of all the Sisters action1 / 30
    (1)Average
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    This newer craftsman style home is walking distance to Downtown Sisters. From the front porch you can view Black Crater. The upstairs family room has a large screen TV and wonderful skylights adding an abundance of natural light. There is a sleeper sofa in this room. The master on the main level...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Internet Access
    • Washer
    • Patio
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rejoice in the scent of pine trees, sage, and beautiful desert landscape when you take a retreat to Central Oregon. This cute bungalow in Sisters is the perfect home base for a group of six, featuring a large outdoor patio with gazebo seating in any weather, access to a shared pool, and more! Up to...
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    Location Information
    Sisters, Central Oregon 97707
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Hot Tub
    • Internet Access
    • Patio
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Whether you're here for the famous Sisters Rodeo or you're just looking for a quiet home-base from which to explore Central Oregon, you can't go wrong with this charming cottage. Your friends and family will love soaking in the private hot tub, while your dog will love having the run of the...
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    Location Information
    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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