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.

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!

Home in Lodges at Bachelor View - Book Now!

Enjoy Bend’s newest west-side neighborhood nestled beside Century Drive, the gateway to Mt. Bachelor and the Cascade Lakes. Our unique location puts you right on the connector trails to the popular Phil's Trail System for mountain biking or casually strolling along the Deschutes river trail. With access to the National Forest in just steps and breweries mere minutes down the road, Pinehaven is as 'Bend' as it gets. Thank you for considering Pinehaven for your stay. We think you’ll love it here!

Romantic Farmhouse near Mt. Bachelor

Relax at a peaceful farmhouse for a romantic weekend, or take your time exploring Bend with friends. Baltzor Farm and Guesthouse is fewer than 2 miles from some of Bend's amazing breweries and restaurants. Smith Rock and Mt. Bachelor are both within 30 minutes of the guesthouse. Catch a concert, float the Deschutes, or go on a bike ride. Our relaxing farmhouse has rustic, old-world charm with all of the modern amenities, including a soaking tub, waterfall showerhead, soft linens, and Starlink.

Westside Sweet Suite - modern 1 bedroom studio...

Enjoy Bend at it's best. Our house is perfectly located on the westside of town, giving you easy access to all of the things that make Bend unique. This suite is within walking distance to the best beer, restaurants and market in town. Enjoy the mountains, rivers, parks and every activity available to you to get the most out of these natural gems. Bend is an outdoor paradise all year round, so get out and play. Come home and relax in this great space, with everything that you could need.

Pointe of Blessing with hot tub and canyon views

Prepare to be blown away by the astounding sunrises , sunsets and awesome moonrises you will enjoy at the Pointe of Blessing. We feel our canyon perch is a gift from God too good to keep to ourselves. Our cozy home sits atop an outcropping of rock which juts out from the canyon rim affording us unobstructed views up and down the length of the Crooked River Canyon. We overlook several holes of the Crooked River Ranch golf course and Smith Rock is visible in the distance to the South.

Mountain Bliss: Gateway to Mt. Bachelor and More

When the mountains are calling, Bend is like nothing on earth. Savor the charms of Base Camp throughout the year in this luxurious and spacious cabin (1200 square feet). Celebrate the great outdoors – best experienced through unparalleled adventures at Mt. Bachelor (18 miles), Phil’s trailhead (15 minutes), the Deschutes River (5 minutes) as well as the endless access to hiking, biking, running trails, skiing, golf, breweries, restaurants, coffee shops, and the Hayden Homes Amphitheater.

Have a Patio Barbecue at a Pet-Friendly House in Midtown

Stoke the wood stove with another log and stay warm and cozy in a colorful plant-filled living room with stylish mid-century modern furniture. When the weather's nice, go outside to play croquet or corn toss and roast mores around the fire pit under the stars. Each bedroom has cable TV....large fully fenced in yard . Dogs are welcome. Limit of 3 with a $35.00 Pet fee. No cats allowed. Wood provided. There is a smart lock on the front door, you will be given the code before arrival.

Modern high-end home, walk downtown

This fantastic modern home is in the sweet spot of Bend...just next door to the Deschutes River, Downtown Bend, parks, restaurants and dining, nightlife, and family-friendly activities. You'll love our home because of the amazing location, the mid-century inspired ambiance, the high ceilings, the people, and the local views. We are the perfect centrally located home for any Bend adventure. Our place is great for couples and solo adventurers. This is not a party house. Sorry no pets.

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).

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.

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.