Search holiday homes in Sisters, OR from 100+ sites!

Pine Street Cottage is the perfect choice for travelers seeking a comfortable and convenient stay in Sisters. Situated in a quiet neighborhood, the cottage is just a short drive from popular parks and landmarks, offering guests easy access to the area's attractions. With a "very good" user and location rating, the cottage has received positive feedback from previous guests.
The spacious 3-bedroom, 2-bathroom vacation home can accommodate up to 8 guests, making it ideal for families or groups. The fully equipped kitchen and private outdoor space provide all the comforts of home, while the free Wi-Fi, TV, and essential amenities ensure a relaxing and enjoyable stay.

The Gem Estate by AvantStay is located in Sisters, Oregon, just a short drive from popular parks like Hollinshead, Drake, and Ponderosa. The peaceful surroundings offer a tranquil retreat for relaxation and enjoying nature. This 5-bedroom, 4-bathroom vacation home comfortably accommodates up to 12 guests. Enjoy modern amenities like a fully equipped kitchen with a dishwasher, air conditioning, a private jacuzzi, a fitness center, and free parking.

This holiday home is located in Bend, 16 to 18 miles from Hollinshead Park, Drake Park, and Ponderosa Park, and 21 miles from Redmond Municipal Airport.
This 2760 square foot house offers 3 bedrooms, 2 bathrooms, and sleeps up to 11 guests with amenities including free WiFi, air conditioning, a full kitchen with a dishwasher and microwave, a balcony with mountain views, a patio, barbecue, and a fireplace.

This pet-friendly, family-friendly lodge in Sisters, Oregon, offers direct access to Deschutes National Forest trails and is located 3 miles from downtown Sisters' shops and dining.
This 3-bedroom, 2-bathroom cabin accommodates up to 10 guests and features a fully fenced backyard with a hot tub, a game room with foosball and ping pong, and proximity to Tollgate HOA amenities including a saltwater pool and tennis courts.

This vacation rental is located within Black Butte Ranch, offering convenient access to the resort's extensive amenities.
This 1240 sq ft house accommodates up to 19 guests and features a full kitchen, fireplace, indoor swimming pool, and exclusive spa facilities including a sauna and hot tub, with Wi-Fi and private parking provided.

This vacation rental is located within Black Butte Ranch, offering direct access to the ranch's extensive amenities and activities.
This 1350 sq ft house accommodates up to 11 guests and features a full kitchen, WiFi, air conditioning, a swimming pool, jacuzzi, sauna, spa, and fitness center.

This expansive 5-acre estate in Sisters offers a secluded retreat, located 22 miles from Drake Park and Hollinshead Park, and 24 miles from Ponderosa Park, with Redmond Municipal Airport 19 miles away.
This grand house accommodates up to 19 guests with 5 bedrooms and 4 bathrooms, featuring a private hot tub, multiple fireplaces, free Wi-Fi, and a fully equipped kitchen with an oven, situated conveniently near ski slopes.

This house at Glaze Meadow 032 is located within Black Butte Ranch, offering direct access to its recreational facilities.
This 1260 sq ft lodge accommodates up to 11 guests with 1 bedroom, 1 bathroom, air conditioning, a full kitchen, a fireplace, and access to a swimming pool, hot tub, sauna, spa, and fitness center, plus complimentary Wi-Fi and private parking.

This Black Butte Ranch Ridge Cabin boasts a prime location, offering easy walking or biking access to Glaze Meadow and Big Meadow golf courses, the Lodge Restaurant, Aspen Lounge, and the Glaze Meadow Recreation Center and Spa.
The three-bedroom, two-bathroom house sleeps six guests and includes a fully equipped kitchen with dishwasher, free Wi-Fi, access to a fitness center and hot tub, plus stunning Aspen Lake views.

The Sisters Moose vacation home is located in Sisters, Oregon, approximately 24-26 miles from Ponderosa, Hollinshead, and Drake Parks.
This 1400-square-foot house sleeps 11 guests, boasting two bedrooms, two bathrooms, a full kitchen with dishwasher, in-unit laundry, free Wi-Fi, cable TV, a private pool, tennis court, and free parking.

This house is located within Black Butte Ranch, offering direct access to the resort's shared amenities.
This 2120 square foot residence accommodates up to 18 guests with 2 bathrooms, featuring a full kitchen, air conditioning, a private entrance, and access to a shared outdoor pool, private outdoor pool, indoor pool, jacuzzi, sauna, spa, and fitness center, with free Wi-Fi and pet-friendly accommodations.

This brand-new house rental is located in Sisters, Oregon, just 0.1 miles from downtown Sisters and a 1-minute walk to Sisters Community Park.
This pet-friendly vacation home accommodates up to 4 guests with 2 bedrooms and 2 bathrooms, featuring a private hot tub, outdoor fire pit, full-size washer/dryer, indoor fireplace, and garage parking.

The Gem Estate, a 2,950-square-foot luxury farmhouse, is located on a 10-acre private lavender farm 15 minutes southeast of Sisters and 25 minutes north of Bend, Oregon, offering easy access to both towns' attractions.
This five-bedroom house, sleeping up to ten guests, boasts a chef's kitchen with Thermador appliances, a private swimming pool, jacuzzi, sauna, fitness center, Tesla charging station, two detached barn suites with private bathrooms, and outdoor amenities including a firepit, disc golf course, and pickleball court.

This Sisters, Oregon cabin sits on the edge of the Deschutes National Forest, a short bike ride or drive from downtown Sisters' shops and restaurants.
The 3-bedroom, 2-bathroom lodge sleeps 8, offering a heated covered deck, hot tub, high-speed internet, and direct access to hiking and cross-country skiing trails.

This Black Butte Ranch vacation home is conveniently located near Phalarope Lake (under 3 miles), Glaze Meadow and Big Meadow Golf Courses (under 3 miles), and within 9 miles of Suttle Lake and the Metolius River.
This 1820-square-foot lodge boasts three bedrooms, two bathrooms, sleeps twelve guests, and features a fully equipped kitchen, indoor/outdoor pools, a hot tub, sauna, fitness center, and tennis court.

This ground-level townhome in Sisters' Pine Meadow community offers easy access to downtown shops, restaurants, and miles of trails.
The three-bedroom, two-bathroom house sleeps six, features a fully equipped kitchen, in-unit laundry, a smart TV, and access to a seasonal community pool and year-round hot tub.