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Sisters Holiday Homes

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    Travellers to Sisters are booking May dates now. Secure your holiday rental today, and have the perfect trip.
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Great Home for Quilt Show or Folk Festival Week1 / 15
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
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    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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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Patio
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    About this property
    This updated cabin blends rustic charm with a modern flare! The cabin is comfortable and light and bright. The kitchen, dining area and three bedroom and three baths are located on the first floor and the living area is upstairs. Adults and kids alike will love the location. It's just a short...
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    Sisters, Central Oregon 97759
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Skiing: Property Is In A Ski Resort
    • Shared Outdoor Pool (Unheated)
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    About this property
    Remodeled in 2015, this 5 bedroom, 2.5 bath beautiful Black Butte Ranch home sits on a double lot, has an upgraded kitchen and bathrooms, and features natural bamboo flooring.  The main level master suite with king bed and large soaking tub provides a quiet sanctuary for guests. Two additional...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    Pet friendly
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    About this property
    This spacious vacation home (2,643 sq. ft) sits on a beautifully landscaped home site with large Ponderosas and vine maple, a perfect habitat for abundant birds and wildlife. The back deck is large, private and very inviting, bordering forest land. There are multiple bird houses and nests and you...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    • Waterfront
    • Mountain Views
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cozy, charming condo is in a prime location. Walk to most facilities and enjoy the stunning scenery Black Butte offers every time you look outside or venture onto the deck! Perfect for the sunbather or wildlife buff or photographer. This condo is ideal for experiencing the true ambiance of...
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    Sisters, Central Oregon 97759
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious (1,744 sq. ft) home has loads of charm and is beautifully updated. Surrounded by Ponderosa Pines and within a short walk to the popular Paulina Springs Pool area, it will be ideal for your family vacation. Paulina Springs Pool, which is as unique as Black Butte and this beautiful...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Pet friendly
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    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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    • Shared Outdoor Pool (Unheated)
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    • Hot Tub
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in the pines of Black Butte Ranch, this winning 3BR/2BA home accommodates eight guests. Comfy furniture, warm wood details, and a cozy wood stove await your arrival. Enjoy entertainment amenities such as ping-pong, darts, and a canoe. The Black Butte Ranch community pool, hot tub, and...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>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...
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    Sisters, Central Oregon 97759
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    • Cable/satellite TV
    • Private Indoor Pool
    • Hot Tub
    • Sauna
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    GM#117 is a spacious, 2,172 sq. ft.vacation home very close to the Glaze Meadow Recreation area. An open floor plan, soaring vaulted ceilings, and warm wood throughout, make it the ideal contemporary getaway. Take advantage of all the ranch has to offer with your pup too! This home is dog friendly....
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    • Internet Access
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This four bedroom charmer is welcoming and close to many facilities. GM#235 is a single level 2,100 sq. ft home with four bedrooms and three baths. The bunk room is off the family room and has a nearby 1/2 bath. Down the east hallway is a queen bedroom with bathroom across the hallway and a king...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Mountain Views
    • Shared Outdoor Pool (Unheated)
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    • DVD Player
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>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,...
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    Sisters, Central Oregon 97759
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Air Conditioning
    • Grill
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    • Hot Tub
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Plan a delightful multi-family getaway to this 5BR/3.5BA rental for 13 guests. With a spacious kitchen and dining area and two living rooms, there’s plenty of room to spread out. Situated just 3 miles from the heart of Sisters on a five-acre wooded lot, the home is private and secluded while still...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 13
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>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...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Cable/satellite TV
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    • Wi-Fi
    • Grill
    • Patio
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your perfect dream vacation home is waiting for you at Black Butte Ranch! GM#135 is a beautifully appointed 5 bedroom, 4.5 bath, 3,505 sq. ft home on the seventh Glaze Meadow Fairway. Located on almost a half acre, not only are the views fantastic, but the home is but a short walk or bike ride...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    6 Bedrooms, 5 Bathrooms, Sleeps 18 Quick View
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    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Mountain Views
    • Grill
    • Wi-Fi
    • Patio
    • Washer
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious home (5,069 sq. ft) has amazing Lodge/Western decor and features breathtaking meadow, mountain and lake views from most rooms.This extraordinary home embodies the essence of Black Butte Ranch and is aptly named the 'Faith, Hope, and Charity Ranch'. The double door foyer opens to a...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 18
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Mountain Views
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning rental home will help make your family's Black Butte Ranch vacation the best ever! A beautiful entry leads to a staircase that enters on the main floor. The room showcases soaring ceilings and windows and natural light from all directions. The 'grand' great room consists of a very...
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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 12 Quick View
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    • Grill
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    • Shared Outdoor Pool (Unheated)
    • DVD Player
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    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 an indoor pool and rec center, is just a few miles away. Your 3,000 square foot...
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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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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>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...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>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...
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    Sisters, Central Oregon 97759
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    • Washer
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>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...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>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...
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    Sisters, Central Oregon 97759
    Cabin Holiday Rental - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Shared Outdoor Pool (Unheated)
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    • Internet Access
    • Air Conditioning
    • Mountain Views
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This condo takes full advantage of the gorgeous views of the 10th Fairway plus the North, the South Sister Mountains as well as Broken Top. There is a large Trex deck where the views are stunning to sunbathe, enjoy the golfers, evening BBQs with family or just relax with friends. This may be the...
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    Sisters, Central Oregon 97759
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Patio
    • Hot Tub
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    • Grill
    • DVD Player
    • Washer
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>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...
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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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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • Washer
    • Mountain Views
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>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...
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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 4 Quick View
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    • Grill
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    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>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...
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    Sisters, Central Oregon 97759
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>Enjoy time with your family & friends at this charming single level 3 bedroom 2 bath home in a great Sisters location. Very open and roomy, featuring a wall of windows providing plenty wonderful natural light. There are partial mountain views from the living room, master...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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
    div class='rtejustify'>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...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Shared Outdoor Pool (Unheated)
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    Kid friendly
    Smoking allowed
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    div class='rtejustify'>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...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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