Vacation rentals in Prineville

A cozy living area features a brick fireplace and exposed beam ceilings. Comfortable seating includes two armchairs and a sectional sofa. A dining table and chairs are visible in the background, along with a well-equipped kitchen. Natural light streams in from windows, enhancing the space.

4.9 out of 5 average rating, 21 reviews

Sunriver Vacation Dreamhome

This vacation home will make your Sunriver stay feel like a dream. 3 cozy bedrooms (1 King & 1 Queen), 3 full baths and 8 SHARC passes. The enclosed spacious deck provides the ideal spot for dining or soaking in the hot tub among the pines. The fully-equipped kitchen allows you to prepare meals while enjoying your creations in the adjacent dining area. If you're seeking outdoor adventure or craving a peaceful retreat, our vacation home promises cherished memories that will last a lifetime.

Superhost

A private balcony features two comfortable chairs positioned on wooden flooring, offering a relaxing spot to enjoy the outdoors. The door to the interior space is visible in the background, leading to a well-lit room with neutral-colored walls.

Condo in Sisters

4.76 out of 5 average rating, 58 reviews

Pine Rest - Escape to this beautiful condo A/C,

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 are tennis courts just a couple of blocks too! This upstairs condo has one queen and two twin beds with air conditioning and is dog friendly, so bring the whole family. Nicely and fully furnished and equipped, vaulted

A two-story home is nestled in a snow-blanketed landscape, illuminated by the soft glow of outdoor lights. Tall pine trees surround the property, and a full moon adds a serene ambiance to the winter scene.

4.96 out of 5 average rating, 117 reviews

Pet friendly, upscale home, AC, sleeps 8

Our beautiful 1900 sq. ft. Home, is the perfect spot for your vacation. Our kitchen has every gadget, and upscale appliances to create gourmet meals. King master upstairs, and 2 queen bedrooms down, share a bathroom. We have bikes and ping pong and TV in the garage. A Weber BBQ on the deck, with a sparkling, bubbling hot tub. Decks face both east and west, so morning sun, and evening sunsets. Dog friendly! (2 dog limit). Warm up by our big fireplace after a fun day skiing at Mt. Bachelor.

4.91 out of 5 average rating, 124 reviews

Cabin in Sunriver

Modern Cabin Oasis Near Village

Huge April discounts ! Hip cabin centrally located on par 3, off circle 1. Play room with New hot tub. Backyard walking trail and 10 min walk to the village and SHARC. Playroom with toys and electric charging station. Sleeps 8 comes with 5 bikes garage space for kayaks. 8 SHARC passes. Center of all Sunriver action. Its small in the rooms but the common areas are large. The trail in the back gives a feel you are in the center of all the action! It has everything you need in Sunriver.

A charming outdoor space features a hot tub surrounded by greenery and colorful flowers. A table with chairs is positioned on the lawn, providing a relaxing area. The cottage, with its gray exterior and red door, is nestled among trees, offering a private retreat.

4.97 out of 5 average rating, 101 reviews

Downtown with hot tub and fenced-in yard

Light and bright downtown Bend vacation cottage with a landscaped, fenced yard and HOT TUB. Walk to breweries, restaurants, coffee shops , art galleries and the Deschutes river and river trail. One-bedroom, one-bath unit features a separate memory foam queen hide-a-bed in the living room. Private laundry room. Private parking spaces in back. Open floor plan with vaulted ceilings and automated skylight shades. Complete remodel. Pet-friendly (must add pet to the reservation).

4.97 out of 5 average rating, 119 reviews

Cottage in Bend

Exceptional Downtown Cottage-Level II EV charger

24 time Airbnb "Super Host" award. 2017/2019 Winner of a "Certificate of Excellence" Exceptional 5 Star reviews for all vacation rentals in the Bend area. The Cottage is constantly being updated including new furniture, appliances, paint, and even painting of the cabinets. These significant investments keep the Cottage fresh and like it was brand new. City of Bend Short Term Rental Operating License: STR-20-0285

A serene outdoor space is surrounded by tall trees and lush greenery. A neatly maintained lawn contrasts with a natural mulch area, while a paved section provides a picnic table shaded by a large umbrella. Sunlight filters through the leaves, enhancing the tranquil setting.

4.9 out of 5 average rating, 319 reviews

Sunriver Gem | Near Deschutes & Mt. Bachelor

Discover our cozy, pristine home, showcasing meticulous care. Experience the charm of leather and log decor, contemporary conveniences, and extensive parking. Our wildlife-friendly yard captivates. Minutes from Deschutes River, Mt. Bachelor, SHARC, and Sunriver Village. Highly rated and affordably priced for an exceptional stay. Enjoy comfort, ease, and unforgettable moments. Secure your memorable escape today!

4.91 out of 5 average rating, 250 reviews

An aerial view captures a snow-covered neighborhood surrounded by tall pine trees. Various residential buildings are visible, with roofs blanketed in white snow. The landscape showcases a mix of homes and open spaces, highlighting the natural beauty of the area.

Condo in Sunriver

Sunriver - Pool/Hot Tub. Minutes to Mt. Bachelor

- This unique and friendly spot boasts a convenient location to Central Oregon's famous outdoor activities. The space is only a 26 minute drive to Mt. Bachelor, the beginning of the scenic Cascade Lakes Highway, and a short walk to The Village at Sunriver. Community pool, hot tub, and laundry are on site and accessible. Wifi and Netflix logins are provided to all guests.

4.97 out of 5 average rating, 114 reviews

An inviting outdoor seating area features a circular fire pit surrounded by cushioned rockers. The lodge-style structure showcases wooden beams and stone accents, bathed in soft evening light from the windows, creating a welcoming atmosphere for gatherings.

Home in Terrebonne

4BR/3Bth, Bend Country Pastoral 9 Mt View, 9 acres

Plan your vacation getaway and escape the destination resorts at our quiet & peaceful 4 BR, 3 Bath, lodge home retreat on 9 private acres north of Bend, "in the country but not far away". Beautiful 9 Cascade Mt view overlooking a corner of the legendary Deschutes R.; enjoy area Skiing, Golfing, Fishing, Hiking, Rock Climbing, Biking, Micro Breweries, & more.

4.97 out of 5 average rating, 34 reviews

Stunning Views@River Sun Resort

Escape to our luxurious Deschutes River Airbnb in Central Oregon! This 3-bed, 2-bath waterfront retreat offers a stunning 180° river view, peaceful ambiance, open floor plan, bikes, and kayaks. Immerse yourself in nature's beauty, relax by the fireplace, and explore the river on kayaks or bikes. Book now for an unforgettable experience!

4.97 out of 5 average rating, 36 reviews

Townhouse in Redmond

Babbling Brookside near Splash Park

Creekside Village on the creek Wi-Fi Resort Passes- 8 Hot Tub Cable TV Gas BBQ Sleeps 8 King Primary Suite Queen Upstairs Bedroom Family Bedroom with Queen and Twin over Twin Bunk bed 1 block from the Lakeside sports center, infinity pool, kids pool, and Splash Park. Fully stocked, beautiful 3 bedrooms and 2 1/2 baths.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Hotels

Stylish accommodations and amenities

Popular amenities for Prineville vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Prineville's top sights

Club Pioneer17 locals recommend

Bowman Museum16 locals recommend

Dillon's Grill15 locals recommend

Meadow Lakes Golf Course9 locals recommend

Crooked River Brewing8 locals recommend

Barney Prine's Steakhouse & Saloon8 locals recommend

Other great vacation rentals in Prineville

5 out of 5 average rating, 75 reviews

Home in Sisters

Stunning Mountain View Home~Unsurpassed views

Superhost

A spacious wooden deck overlooks a lush forest of pine trees, providing a serene outdoor setting. A metal table surrounded by four chairs is complemented by two green cushioned loungers, while an umbrella adds shade to the seating area.

4.95 out of 5 average rating, 105 reviews

Deschutes River Getaway-near Bachelor & Sunriver

Superhost

The exterior of the chalet is showcased, featuring a peaked roof and large windows that reflect the sunset. A spacious deck with railing is visible at the front, surrounded by a well-manicured lawn and tall trees, providing a calming natural setting.

Home in Redmond

4.83 out of 5 average rating, 29 reviews

Dog Ok! Full Resort Access. Garage - Cozy Chalet

4.99 out of 5 average rating, 72 reviews

A classic two-story house is set against a vibrant sunset sky. The wrap-around porch features soft lighting, while neatly landscaped gardens with tall grass enhance the welcoming ambiance. Concrete pathways lead up to the entrance, complemented by lush greenery lining the yard.

Home in Sisters

Downtown Pine Mountain Paradise

4.99 out of 5 average rating, 113 reviews

A spacious living area is displayed with a large sectional sofa arranged around a soft area rug. Natural light brightens the space through the window, while a modern dining area is visible in the background, featuring a long table. Wood flooring adds warmth to the room.

Condo in Sisters

Beautiful Sisters Condo - Great location

4.8 out of 5 average rating, 5 reviews

Stellar Cabins

5 out of 5 average rating, 19 reviews

Townhouse in Redmond

The Great Escape at Eagle Crest