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.

Park Place *Modern + Fenced*

Enjoy our convenient Downtown location! Just a short walk to Downtown Bend, the Old Mill District, and the popular Box Factory shops/restaurants. This recently updated house has a modern vibe with ample parking and cozy beds (1 King and 2 Queens). It has fast Wi-Fi & a desk in the master bedroom for those working remotely. The Living room has an Amazon Firestick to easily stream content from your online accounts. We have a fenced in yard with paver patio to relax outside. Come relax and enjoy!

Laverne - Historic Home in Downtown (new hot tub!)

Laverne is a one bedroom historic cottage tucked in between two larger houses, with access from both Georgia Ave and Lava Road. Unique for it's proximity to downtown AND the peaceful residential feel. Mature landscaping with heritage cherry tree, private and sheltered bungalow. Outdoor space includes private deck and hot tub with views; small enclosed front yard. Full kitchen, washer/dryer. Queen Casper in the tiny bedroom. Sleeper sofa in living room. Great natural light. Off street parking.

Park Place - Walk to Downtown & Old Mill

Welcome to Park Place! This house in Downtown Bend is 100 years old, blending modern comfort with historic charm. Walk 5 min to Jackson’s Corner, 7 min to the Box Factory, 8 min to Crux, 12 min to the Old Mill, and 15 min to Downtown shops. The home offers strong WiFi, smart TV, a stocked kitchen, and outdoor seating. Nearby activities include the Deschutes River Trail, Drake Park, Hayden Homes Amphitheater, and easy access to breweries, lakes, hiking, skiing, and Central Oregon adventures.

Downtown Craftsman with King Bed and Private Yard

Stay at a rare home in the core of downtown. A beautifully restored 1922 craftsman with plants and warm wood throughout including natural light from vaulted ceilings, charming architecture and paintings by local artist Sheila Dunn. Walk to dozens of restaurants, breweries, coffee and shops. Cross the alley to food trucks and frequent live music or relax in your private walled courtyard. No parties or pets please. Trip insurance recommended if illness, weather or smoke may be an issue.

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.

Westside "Bud-And- Breakfast"

The first and only "Bud-And-Breakfast" in Bend, Or, located in the heart of Bend's Westside. Situated above Tokyo Starfish, the unparalleled cannabis dispensary in Central Oregon, this fantastic 2-bedroom apartment isn't just in a great location, but is also cannabis friendly. Just head downstairs to Tokyo Starfish with your complimentary gift card and experience the freshest selection of flower, edibles, drinks and other top cannabis products the dispensary has on hand.

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.

Stylish Cozy bungalow w/ theater

Escape to a cozy haven in Bend with heated floors, contemporary artistic design, and a perfect central location near parks, breweries, and food carts. Immerse yourself in a high-end movie theater boasting an 11-foot screen, twinkling star ceiling, and state-of-the-art Dolby ATMOS surround sound. Perfect for getaways, business trips, or a cozy retreat while exploring Bend. This modern home in a lovely neighborhood is the perfect base camp for your Bend adventures!

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.