Close to downtown Sisters

These properties are located just outside of downtown Sisters. Some are within walking or biking distance.


Properties Available 25 properties available
Three Peaks Retreat is a beautifully decorated townhouse located in a quiet family neighborhood of Sisters Oregon.  Accommodating up to 6, it's perfect for the family getaway or friends retreat you have been planning.  A cozy and inclusive design, with plenty of space for everyone, you will have no problem entering relax mode.You will feel right at
Hot HOT 21
Three Peaks Retreat
3 Bedrooms
$148 - $310 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.5 (4)
Jacob’s Ladder is a charming 3-bedroom, 2 1/2-bathroom family friendly vacation home ideally located in the community of Black Butte Ranch. With so much space, it is perfect for a family vacation, or getting together with friends. Inside, the well-appointed kitchen, complete with bar stools, opens up to a dining room for more formal meals. Relax in
Jacobs Ladder - Black Butte Ranch
3 Bedrooms
$118 - $486 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 9 guests
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
$84 - $268 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 5 guests
Rating 4.9 (34)
The serene Sisters Chalet presents a haven of tranquility, granting breathtaking vistas of the surrounding mountains and lush meadow. Embrace a retreat that feels worlds away, yet 1.5 miles to downtown Sisters, where a plethora of distinctive boutiques and eateries. For ski enthusiasts, this locale is an idyllic haven, positioned 23 mile from Hoodo
Hot HOT 21
Sisters Chalet
1 Bedroom
$58 - $172 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.9 (14)
Experience a deep togetherness in this spacious home designed for engagement and cozy connection. Mindfulness here can include: Cooking together in the well-appointed chef’s kitchen, star gazing through wide views of mature pine and juniper, nestling into one of several large or small gathering areas to suit the intimacy of conversation, marinating
Hot HOT 13
Kittyhawk Retreat
3 Bedrooms Pet Friendly
$128 - $405 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (1)
Experience a Tranquil Getaway at our 2-Bedroom Condo in Pine Meadow Village, Sisters OregonWelcome to our charming 2-bedroom, 2 full bath vacation rental condo located in the peaceful Pine Meadow Village neighborhood of Sisters Oregon. This delightful vacation retreat offers a comfortable and relaxing experience for up to 6 guests.Upon entering, yo
Hot HOT 56
Big Mountain View Condo
2 Bedrooms
$122 - $433 / 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
$198 - $541 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 10 guests
Welcome to Fairway View, a distinctive residence located on the 7th hole of Big Meadow golf course, in the prestigious Black Butte Ranch community.Inside, this three story home boasts generously sized living areas, perfect for family gatherings and entertaining. On the second level you will find a well-equipped kitchen featuring modern appliances,
Hot HOT 15
Fairway View
5 Bedrooms
$144 - $1,059 / per night
Bedrooms 5 bedrooms
Guests 11 guests
The 4th Sister Lodge - Bottom floor, easy access to assigned parking. These condominiums are surrounded by Creekside park where Whychus Creek runs year round. The complex features a seasonal pool and year round sauna and hot tub. Also a club house with a pool table, ping-pong, foosball and a fitness area. It's an easy walk to the historical town o
Hot HOT 13
Fourth Sister Retreat
2 Bedrooms
$155 - $402 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
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
Hot HOT 11
Canyon Perch
3 Bedrooms Pet Friendly
$124 - $302 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Newly remodeled 2 bedroom 2 bath home just outside of Sisters.  Located on a private, wooded, one acre lot in Crossroads.Your dog will enjoy this vacation as well with a fully fenced front yard.  This is the enchanted area of the explorers Lewis and Clark, offering miles and miles of rivers, lakes, forest, and stunning mountain peaks.For the golfer
Hot HOT 17
Bluegrass
2 Bedrooms Pet Friendly
$88 - $264 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Previously known as Sister Home Lower, Sisters Retreat Lower allows you to experience a fresh and contemporary getaway that exudes warmth and positivity. This charming accommodation offers everything necessary for a delightful stay, all within a short stroll to the vibrant downtown area, where ample parking awaits.Designed to cater to those intendi
Sisters Retreat Lower
1 Bedroom Pet Friendly
$58 - $169 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 5 guests
Rating 4.8 (16)

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