Black Butte Ranch: NW Contemporary This well-appointed Black Butte vacation home is perfect for families, friends, or couples traveling together, offering amazing resort amenities including four pools, two golf courses, tennis courts, horse stables, and beautifully landscaped biking and walking...

Black Butte Ranch: Hilltop Getaway Take a trip with family and friends to this astounding Black Butte Ranch vacation rental and experience Central Oregon from the comfort of a resort community with golf, tennis, aquatic recreation, and outdoor recreation galore! Black Butte Ranch is located 32...

Cathedral In The Trees - Tollgate Sisters 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...

Black Butte Ranch: Aspen Grove Retreat (GM 3) Visit the fabulous Black Butte Ranch and live in style and comfort in this gorgeous home while you enjoy all the nearby activities! Featuring a sunny and welcoming interior, private hot tub, access to amazing community amenities, and room for eight...

Mollie's Cottage Downtown Sisters 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! Sisters' central business district is just a few blocks north and west of this...

Sisters Tollgate Retreat with Hot Tub & WiFi This home in the heart of Tollgate offers guests a private hot tub in the spacious backyard, beautifully restored bamboo floors back inside, an acre of pine-shaded land to explore, and shared community amenities like a swimming pool, tennis court, and...

Rock Ridge 39 *At check-in, the resort will collect a $9 daily fee for every guest seven years and older. This open-concept and dog-friendly Black Butte home is just the place for your family's next vacation or get-together with friends. The home features large bedrooms with two offering their...

Black Butte Ranch: Luxurious Getaway in the Pines This elegant and spacious Black Butte Ranch vacation rental is perfect for a getaway with your large group. There's plenty of room for everyone to hang out among this home's generously sized common areas, which include a large game room in the...

Peters Tollgate Cabin 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...

Black Butte Ranch: Glaze Meadow Home Wonderfully appointed multi-level Black Butte Ranch home with three bedrooms, loft, WiFi and private hot tub. The peaceful acre with towering Pines and views out towards the Glaze Meadow Golf Course offers a wonderful private setting. The small loop is ideal for...

Black Butte Ranch: Partridge Foot Cabin lot #RR83 Enjoy a getaway to Central Oregon's great outdoors when you take your family to stay at the wonderful Black Butte Ranch Resort. Perfectly located for a winter retreat or a summer adventure, this fantastic vacation home is a great choice for pretty...

Black Butte Ranch: Hedge Nettle Cabin This fabulous Black Butte Ranch vacation rental offers rustic charm with an outdoor patio, resort amenities, wood-burning fireplace, and space for six. Hedge Nettle Cabin is a perfect hideaway for outdoorsy families and vacationing couples. The Deschutes...

Sisters Downtown 1930s Cottage 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...

Among the Trees and On the Trails Escape to nature at this spacious home in Black Butte Ranch, a deluxe vacation lodge surrounded by evergreen forests close to golf courses, hiking trails, waterfalls, and lakes. This secluded home has a private hot tub and is also just 10 miles from the charming...

Black Butte Ranch: Grey Owl Getaway On The Greens Looking for a comfortable and stylish retreat for your next family vacation? This Black Butte Ranch charmer offers a private hot tub, lots of room, and a swanky mid-century style all with deluxe resort amenities like shared pools, multi-use trails,...

Glaze Meadow 99 Glaze Meadow 99 is a place to relax, rejuvenate, and enjoy time with family or friends. Tranquil views of the woods, the Glaze Meadow second fairway, and Black Butte are seen through panoramic windows. An open-concept kitchen, dining, and living area allow room for family or friends...

Desert Vista This beautiful house in Sisters sits on a large plot surrounded by gorgeous mountain views and fragrant fields of sage removed from the noise of civilization. There's a gourmet kitchen with breakfast seating, French-style doors opening onto the patio, and plenty of seating inside and...

Cozy on Big Meadow Treat your friends and family to a relaxing countryside getaway with this home at Black Butte Ranch. This great location offers lots of privacy, and you'll be right under the mountain, with easy access to hiking, community perks like a shared pool and hot tub, and a fully...

Glaze Meadow 252 This stunning Black Butte home, with its clean lines and modern furnishings, is the perfect location for your next big family vacation or getaway with friends. This home showcases a collection of Western art and features a downstairs game room with Ping Pong and a pool table. The...

Sisters Haywagon Bungalow 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...

Pride of the West This rustic-style cabin in Black Butte has a cozy interior with all the modern conveniences your family needs to feel comfortable. It boasts premium leather furniture, a wood stove, and four flatscreen LED TVs (family, living room, and both master bedrooms). The deck has a gas...

Black Butte Ranch: South Meadow Home Eighty-Four Do yourself a favor and make this spacious, enticing rental near Black Butte Ranch your home base when you're ready for your next unforgettable mountain escape. With four bedrooms, a shared pool and hot tub, and loads of other amenities, you'll be...

Sisters Tollgate Cabin with WiFi Sisters Tollgate Cabin is nestled among the pine trees on the edge of 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...

Glaze Meadows Fairway View If sunshine and blue skies are on your list as must-haves for that next great family vacation, then this bright and roomy Black Butte home is the one that should satisfy all your needs. The home has multiple living areas and large windows throughout that provide an...

Casa de los Caballos This historic Sisters ranch is ideal for horse enthusiasts and is the perfect spot to set up a base for the Sisters Rodeo. The ranches charming guest house has been lovingly restored with fresh paint inside and out, plus new beds and kitchen appliances. The western theme of...

Meadow Grass Golf Retreat Experience the exhilarating year-round beauty of Black Butte Ranch at this three-bedroom home, a gorgeously situated Central Oregon retreat with an expansive deck, an unbeatable golf course-front location, and community amenities that include swimming pools, hot tubs,...

Black Butte Ranch: Hawks Beard Home At the western edge of Black Butte Ranch is a getaway whose comfortable charm and renewed amenities blend perfectly with the spectacular surroundings. It’s a well-appointed but cozy retreat, dog-friendly, and hot tub-equipped, making for a relaxing headquarters...

Sisters Tree View Sisters Tree View is a beautiful, upscale home with an ideal location in the charming town of Sisters. This stunning home features an open floor plan with vaulted ceilings, wonderful wood finishes throughout, and a spacious kitchen with natural edge granite countertops and...

Black Butte Manor Bordering Forest Windows surround this warmly furnished home's living and dining areas, revealing a fireplace and stone hearth at the center, as well as the beauty of the Deschutes National Forest right outside your back deck. The whole family will love the game room, complete...

Glaze Meadow 129 With its great location, Glaze Meadow 129 is the ideal home for your families next vacation or weekend getaway. The main living area features a large wood burning stone fireplace that is the perfect spot to gather in on cold winter days. The upstairs loft has a big screen TV, with...

McKinney Butte Getaway This beautifully updated home is the perfect place for exploring Sisters and all that it has to offer. The open concept living area with its large kitchen and breakfast bar offers a comfortable area for friends and family to enjoy their time together. The fenced backyard's...

Glaze Meadow 7 Make your next vacation to Central Oregon special and stay in this comfortable resort home in Black Butte. With access to a shared pool, hot tub, sports courts, and more, up to eight guests will have a remarkable time here. Located in the upscale Black Butte community just eight...

Lucky #7 Feel the classic cabin charm of this comfortable home in Black Butte Ranch. Featuring one bedroom plus a loft with a chair that folds out into a twin bed/cot, this cabin sleeps five, making it perfect for a family, two couples, or just you and your furry friend. Enjoy its cozy,...

Sisters Downtown 1930s Cottage with Extra Studio 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...

Apache Greens This home is perfect for relaxing after a day of exploring. After a day on the slopes, soak your weary muscles in your private hot tub. Outside, gather aound the firepit, whip up some dinner on the grill, or play in the large yard. In the evening, enjoy a drink by the pond, watch the...

Country House Condo 63 Treat your friends and loved ones to an unforgettable Central Oregon retreat when you stay at this Black Butte Ranch vacation rental! Whether you're here for relaxation or adventure, you'll enjoy this condo's convenient location (within walking distance of Black Butte Ranch...

Sisters: Whychus Creek Craftsman 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, with access to the Wychus Creek right out the back door. Located in a quiet neighborhood in downtown...

Black Butte Ranch: Glaze Meadow Homestead This three-bedroom Black Butte Ranch home offers guests access to the resort's recreation like golf, pools, and paved bike trails, plus a wooded setting for a rustic getaway with hints of luxury. Located about 10 miles northwest of Sisters and 34 miles...

Black Butte Ranch: Spring Home 6 Black Butte Ranch is a sprawling, family-friendly getaway in the heart of Central Oregon. This wonderful original ranch home offers an ideal living arrangement to share the home with two families. The half acre lot offers a great feeling of privacy to enjoy the...

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...

GM#349 is a spacious 2,855 sq. foot reverse living home that sits on a quiet cul-de-sac at Black Butte Ranch. It sits on over an acre with stunning views of the #14 Fairway of Glaze Meadow! When you enter the great room of this home, you are struck by the beautiful wood walls and trim, tall...

Serious Quilters or Folk Festival friends 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. $425/night with a minimum of 2 nights. Great outdoor...

This recently updated cabin blends rustic charm with a modern flare! The cabin is a spacious 1546 square feet, comfortable and light and bright, (lots of new windows and doors)! The kitchen, dining area and three bedrooms and three baths are located on the first floor and the living area is...

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...

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...

This cozy (1,122 square foot), 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...

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...