Vacation Rentals


Properties Available 53 properties available
Previously known as Sister Home Upper, Sisters Retreat Upper is new and modern, bright and cheery, with all you need for comfortable lodging with short walk to downtown and plenty of parking.If you plan to be out and about most of the time you are visiting Sisters, this place is perfect and comfortable for up to 5 people.Park the car, close to ever
Sisters Retreat Upper
1 Bedroom Pet Friendly
$85 - $198 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 5 guests
Rating 4.9 (34)
Rise and Shine is a gorgeous, 3 bedroom home 2 bathroom, nestled in a quaint neighborhood Pine Meadow Village just steps away from downtown Sisters! Accommodating up to 6, it's perfect for two small families, a couples trip, or a friends getaway! Our spacious layout and our cozy design will have you entering "relax" mode from your first steps insid
Hot HOT 17
Rise and Shine
3 Bedrooms
$129 - $478 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (14)
We would like to welcome you to Sophie's Chateau, located in the beautiful community of Eagle Crest, a 5 Star Resort.  When entering the condo, you will notice the open concept living space and wonderfully high ceilings. The large living space has a sectional with recliners, enough seating for the whole group, a gas fireplace, and TV for you to rel
Hot HOT 10
Sophie`s Chateau
3 Bedrooms Pet Friendly
$129 - $238 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (2)
Escape to this charming and budget-friendly vacation retreat, perfect for two couples or a small family. With two inviting bedrooms and two bathrooms, this cozy haven comfortably accommodates up to six guests.Nestled just a stone's throw away, you'll discover the Tollgate seasonal pool, a tennis court, basketball court, a delightful children's play
Hot HOT 53
The Sisters Moose
3 Bedrooms
$99 - $194 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (20)
Nestled along the tranquil banks of the Metolius River, this charming cabin offers a serene and picturesque retreat from the hustle and bustle of everyday life. Surrounded by lush greenery and the soothing sounds of flowing water, the cabin provides a perfect blend of coziness and modern comfort.The exterior of the cabin boasts a back porch offerin
Metolius Cabin 5
2 Bedrooms
$225 - $496 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
This ground level condo is located in the tranquil 4th Sister Lodge condominiums. Sitting just outside of downtown Sisters, this cozy and inviting two-bedroom, two-bathroom vacation rental is the perfect place to unwind and enjoy all that this beautiful town has to offer. As you step inside, you will be greeted with a bright, inviting, open living
Hot HOT 10
Fourth Sisters Escape
2 Bedrooms
$119 - $200 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
This wonderful retreat is a newly updated, 3-story “A”-frame cabin located in the quaint community of Crossroads in Sisters, Oregon that can sleep 10 people comfortably. The private home backs up to the natural public lands of the Deschutes National Forest, yet is located just 3 short miles from downtown Sisters with all of its year-round charm. Yo
Hot HOT 15
Juniper and Pine - A High Desert Lodge
3 Bedrooms Pet Friendly
$199 - $517 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 10 guests
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 a 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-round spa and seasonal pool privileges are included
Hot HOT 11
Riley`s Mountain View
2 Bedrooms Pet Friendly
$119 - $334 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (17)
Welcome to your own private oasis at this stunning vacation rental in Sisters, Oregon. This 40-acre ranch is bordered by 3,500 acres of BLM land, providing you with ample opportunities to explore the great outdoors. With the main house boasting 5 bedrooms and 3 full bathrooms, as well as a 1-bedroom yurt with 1 full bathroom, this property can acco
Jumping Juniper Ranch House and Yurt
6 Bedrooms Pet Friendly
$379 - $1,194 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 12 guests
Welcome to our charming upstairs condo nestled in the beautiful town of Sisters, Oregon. This delightful vacation rental offers a perfect blend of comfort and entertainment, making it an ideal retreat for families or groups of friends. As you step inside, you'll be greeted by a warm and inviting living space adorned with a cozy fireplace, creating
Fourth Sisters Hideaway
2 Bedrooms
$119 - $197 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Come enjoy this newly remodeled three bedroom two and a half bath home located in Sisters (Timber Creek Development).  This home is perfectly located to enjoy all Sisters has to offer.  Whether you are coming for one of the great events this town puts on or just wanting to getaway for a long weekend this home is a great choice. Come and enjoy our p
Hot HOT 11
Timber Creek Escape
3 Bedrooms Pet Friendly
$90 - $265 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 5 (13)
Time for a romantic getaway? Whychus Canyon home 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, and stargaze. Located 7 miles NE of Sisters Oregon, this newly built home is situated on over 1 acre at
Canyon Perch
3 Bedrooms Pet Friendly
$125 - $268 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests

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