House holiday rentals in Prineville

4.91 out of 5 average rating, 204 reviews

Light-Filled 5BR, Great location!

Our corner home sits on a tree-lined block within a family neighborhood with two private parks and walking paths. While snow-capped peaks can be enjoyed from our windows, the home is conveniently located in town on the desirable Westside. Our spacious 3300 sf home is central to Bend's many amenities. Phil's Trail, a mountain biking Mecca, is just seven minutes away past Mount Washington and Skyliners Drive, the main cross streets of our neighborhood. Broken Top Country Club and golf course is adjacent to the neighborhood off of Mount Washington Drive. The Bend Athletic Club is six minutes away on Mount Washington. Cascade Lakes Scenic Byway, the gateway to Mount Bachelor, is also off of Mount Washington Drive. Skiing and recreational areas at Mount Bachelor can be reached in less than 30 minutes. Historic Downtown Bend is just over five minutes away by car and within easy walking or biking distance. The Old Mill District, which has a spectrum of dining, entertainment and shopping opportunities is also only minutes away by car. The Southern Crossing bridge which links us to Old Mill also leads to the Deschutes River. Within two minutes (1/2 mile away) are neighborhood conveniences at Northwest Crossing, as well grocery stores, pharmacies, restaurants, and bike and ski shops off of Century Drive and Galveston. For rock climbers, Smith Rock State Park in Terrebonne is just 45 minutes away. Sleeping arrangements: comfortably sleeps 10 (on beds, not sofas) Bedroom 1: King bed with sofa/futon and master bath Bedroom 2: King bed with window sitting area Bedroom 3: Queen bed Bedroom 4: Queen bed Bedroom 5: 2 twin beds total (no mattresses in trundles) Dining areas: Rectangular dining table with seating for 10-12 Oval dining table with seating for 6 Island bar with seating for 3 Great room living area: 2 large sofas 2 large arm chairs 2 leather chairs 2 upholstered benches/ottomans Seats 10-12 with additional seating nearby Amenities: Free Wifi High definition cable and 4 TVs Hot tub Game room with board games, books and Wii Air hockey table Table tennis (ping pong table) Foosball table Consumables provided: shampoo, conditioner, body gel, hand soap, dish soap, sponge, aluminum foil, plastic wrap, laundry detergent Parking: Garage parking for one large vehicle or plenty of bike storage Parking for two cars in driveway Corner home with plenty of street parking Thank you for your interest! **No pets. No smoking. No parties. No exceptions. ***Maximum occupancy of 10 for rates listed. 11th and 12th person possible with owner agreement and $25/per person per night. *****One week minimum booking during the Holiday period in December through New Year's. 3-night minimum booking during High Season in the months of June through August. If there is a gap in between bookings, a shorter reservation is definitely possible.

4.91 out of 5 average rating, 130 reviews

Trendy West Side by 10 Barrel, Hot Tub, Fence Yard

The Galveston House is located on the trendy and popular west side of Bend, in the heart of the Galveston District. It is within strolling distance of area hot-spots like 10 Barrel Brewing Company, Victorian Café, Phil’s Growlers, Ariana, Paradise Produce Stand, and The Lot---a great Food-Cart court with outdoor dining. The Galveston House uses solar power and was designed with green efficiency in mind. We have used wonderful re-claimed, one-of-a-kind items to make this home warm and welcoming.

4.88 out of 5 average rating, 351 reviews

House on the Hill. West Hills Sleeps 8, dog OK!

Bends Best Westside Location! Dog friendly! Gorgeous private four bedrooms, three full baths. Sleeps ten! Relax in our private Saline Hot Tub. Huge luxury open floor plan and outdoor space. Two minutes to Newport Market and fabulous restaurants. Enjoy our large gourmet open kitchen, rap-around bar, living room, fireplace, and dining room for your family and friends. Huge extra family room with ping pong table. Newly Renovated! Super Comfy beds and pillows! Close to Mt.Bachelor Ski Resort.

4.96 out of 5 average rating, 117 reviews

Home in Sunriver

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.

4.99 out of 5 average rating, 234 reviews

Perfect walkable location, the best Bend Bungalow

The Kingston Bungalow will provide you with a truly authentic Bend experience. Walk to some of the best restaurants, pubs and markets in Bend. Stroll across the river to downtown Bend or use the cruiser bikes and ride to the Old Mill, Drake park or the river wave at McKay park. This home offers easy access to Mount Bachelor and Phil's Trail and many beautiful hikes, river paddles or x-country ski trails. End your day with a soak in the hot tub or cozy up by the fireplace or gas fire pit.

4.92 out of 5 average rating, 399 reviews

Five minutes from old mill with hot tub.

Welcome to Bend, This is a 1200ft sq three bedroom house. Newly renovated and decorated. Centrally located off of Reed Market Rd. On a half acre lot with plenty of off street parking. Barbeque, chill out space, and small but well stocked kitchen. Walking distance from the new lake spar swimming and fitness center. We do enjoy welcoming four footed guests. There is a secondary full time air bnb guest quarters attached to the main house but rented out separately

Superhost

4.88 out of 5 average rating, 104 reviews

Wooded river retreat near Sun River & Bend

Enjoy skiing, hiking, fishing, kayaking (2 provided) -- you name it -- from our peaceful Deschutes River 3-bedroom home. Inside: -Cozy living room -- w/pull-out bed & TV (fiber WiFi) -Kitchen & table which seats up to 8 (w/extensions) -3 bedrooms: Master, room w/queen, & room w/2 twins Outside: -Porch w/rocking chairs & table -Back patio w/table & BBQ -River 5 min, marina 15 min walk Location: -5 min Sun River -20 min Bend -30 min Mt. Bachelor *Dogs welcome: $75 per dog

4.99 out of 5 average rating, 131 reviews

West House: 2 blocks to River-walk/bike everywhere

Location, Location, Location: This bright and spacious family friendly three-bedroom home is walking distance to the very best of Bend. The river, Old Mill, breweries such as 10 Barrel, Good Life, and Sunriver; Drake Park, downtown and miles of hiking and bike trails are right outside your door. We are centrally located for any Bend adventure whether that takes you to the top of Mt. Bachelor or down the Deschutes River. Our home is great for families, couples, and pups.

4.97 out of 5 average rating, 163 reviews

Old Mill Charm

Great Location in Old Mill District – Walk to Summer Concerts! ♥ Fenced Backyard ♥ Pet Friendly Nestled in the heart of Bend, Old Mill Charm offers the perfect blend of comfort and convenience. Thoughtfully designed with many amenities to ensure a seamless stay, this charming rental is ideal for relaxing or exploring all that Bend has to offer. There is a tenant in the apartment above the detached garage who does not use the driveway or backyard, ensuring your privacy.

Superhost

Home in Sunriver

4.9 out of 5 average rating, 102 reviews

Close toVillage & SHARC pass, AC, HotTub,Sauna,pet

We are happy to share our Sunriver home with you. Enjoy the private location with no through traffic. Central air-conditioning, private bedrooms, hot tub, Viking cedar sauna, wood burning fireplace, and classic Sunriver vibe. Our spacious open concept house is unique in its location, easy short walking or biking distance to the village and SHARC, but quiet and private. 10 SHARC passes included for 2025-26. This is a $300+ value per day.

Superhost

4.95 out of 5 average rating, 105 reviews

Deschutes River Getaway-near Bachelor & Sunriver

Our charming family home is the perfect place to relax and enjoy the outdoors. Just a short walk from the Deschutes River, you'll find miles of walking and biking trails, a pool, tennis and pickleball courts, and docks to launch your raft or kayak. And, with its convenient location, you're just 10 minutes from Sunriver Village, 25 minutes from downtown Bend, and 30 minutes from Mt. Bachelor.