House holiday rentals in Bend

Modern retreat in central Bend

Enjoy our new custom-built ADU located a block away from the Deschutes River in a quiet residential neighborhood, just a 10-minute walk from downtown along the River Trail. In this modern, bright, and private space, you'll enjoy the luxuries of hardwood floors, waterfall countertops, a built-in workspace, heated tile bathroom floors, a 55" Smart TV, BBQ and fire pit, and endless hot water—plus off-street parking and EV charger. One king bed, one daybed with a trundle, and one queen sleeper sofa.

Value · Family · Amenities

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.

Family · Value · Indoor spaces

Butler Corner - New, Clean & Minutes From Downtown

Relax and enjoy all that Central Oregon has to offer in this nice, clean and newer 2019 built home. Butler Corner is located in Midtown and sits on a corner lot in a nice quiet and charming neighborhood just minutes from Downtown. We invite you to stay a while in this comfortable space and think of it as your home away from home. ***Please keep an eye out for posted road signs, I recommend using Google or Apple Maps to help navigate the temporary one-way directions. Completion late Fall 2026

Value · Family · Accuracy

Cozy Three Story Lookout Tower

Thank you for your interest in The Cozy Lookout Tower! Our unique vacation home is really a destination location rather than just a place to stay while you explore the area. Many of our guests are repeat guests that use our home as a place to recharge, relax, cook, read, talk, play games and connect with that special someone. There are some lovely hikes in the area, we encourage you to bring your dog and enjoy the beautiful surroundings by taking some hikes then returning for a soak in the tub!

Value · Family · Condition

THE TROUT HOUSE a cabin on the River

Enjoy our TROUT HOUSE INN all to your self. 40 feet from the shore. Jump in and swim or float or fish, or just sit a take in the view, you won't be able to do much else. From the moment you walk you will feel the love Sunriver Resort is just 5 miles away . Bend is 30 minutes away. you The High Desert Museum is 20 minutes away. Creator Lake is 2.5 hours away. We are only 17 miles to Mt Bachelor. It's a very private setting in a special place in the world. You may never leave.🐠 DCCA64390

Location · Family · Quiet

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.

Family · Location · Laundry

Airy Bend Oasis - Two Ensuites

Cheers to your stay at Bent Pine Oasis, located in the picturesque west side of Bend! This home provides the ideal location for any outdoor enthusiast: Mt Bachelor's slopes are just a 20 minute drive & the Deschutes River Trail is mere steps from the front door- your avenue to biking, running and exploring Bend. Looking for a more relaxing day? You can make the 5 minute drive into the Old Mill District to enjoy food trucks, a river float, or fresh hops at a local brewery.

Location · Family · Checkout

Mid Century West side home-walk everywhere

Newly built mid century ranch has 2 bedrooms/2 bathrooms with a king sized hide-a-bed in the large living area. Home is 4 blocks from Newport Market and a 10-15 minute walk into downtown Bend. Just walk a couple of blocks down the hill and you'll be on Newport Ave, where you can enjoy many of Bend's west side favorite restaurants and coffee shops. This architectural home features an open floor plan with high ceilings, towering windows and quality finishes throughout.

Location · Family · Check-in

Zen w/ Hot Tub, Office, Yard, Dog Friendly, Park

Welcome to your peaceful Bend basecamp, thoughtfully managed by The Home Co.—a local small business focused on clean, well-functioning homes with easy checkouts. This stylish 2-bedroom, 2-bath home is centrally located near Ponderosa Park and Pilot Butte, with easy access to Downtown, the Old Mill, and the Deschutes River. With a fully fenced yard, dedicated office, hot tub, and flexible living space, it’s perfect for families, remote workers, and pet lovers.

Location · Family · Biking

Central Modern Guesthouse with EV Charger

We built this home out of a passion for creating welcoming spaces. Years ago, we renovated a motel on the coast - an experience that sparked our love of hospitality and shapes how we host today. We live around the corner with our kids, a golden retriever, and a few cats. Mike’s a local realtor, and Betsy manages business ops for the local fire department. We love books, music, and helping you discover the best of Bend - trails, eats, and community.

Value · Location · EV charging

Drake Park Cottage in the Heart of Bend

This location can’t be beat! The cottage is steps away from Drake Park and the river as well as walking distance to downtown. Enjoy summer festivals in the park, floating or stand up paddleboard on the river. Located in the historic parks district, this property is quiet and comfortable yet close to all the action. Guests have been coming back year after year to enjoy this unique vacation spot. It’s a gem! SORRY NO PETS and NO SMOKING.

Family · Location · Kitchen

The Land of Aus

The Land of Aus is your quick ticket to relaxation. This charming rustic mountain home is less than a 5 minute walk from the Deschutes river and has everything you need to find solitude and tranquility. Amenities to help you unwind include a hot tub with delightful canal views, a cozy fireplace, clawfoot tub and a Finnish sauna to help sooth those muscles after a long day in the Central Oregon Outdoors.

Value · Location · Hospitality