Family-friendly 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.

The Oasis Airstream

Reconnect with nature at this unforgettable escape, surrounded by gorgeous desert views. Beautifully designed and fully equipped for your comfort. Pet friendly and located just 15 min from downtown Bend. The Oasis Airstream is on a quiet 10 acres. I live here with my family and have a small farming business. There is an ample yard with outdoor table and chairs, outdoor couch, and fire place. There's also a hammock for swinging in the shade on those long summer evenings. Please read all info.

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.

River Run Bend Bungalow & Romantic Spa Grotto

**NEWLY INSTALLED! ** Spa & sauna grotto is all ready for your romantic Bend getaway! This quiet, wooded, centrally located, standalone bungalow is steps from the Deschutes River trail, easy walking distance to Mill Dist. and Hayden Amphitheater. It boasts a comfy king bed w/premium down bedding & pillows, dedicated free parking (+ extra cars or small RVs), outdoor dining and patio area, washer/dryer, and a kitchen fully stocked with everything you need for fun and relaxation for all seasons!

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.

Welcome to Dome Sweet Dome

Your chance to stay in a true-to-name Geodesic Dome! This one-of-a-kind retreat blends comfort with architectural charm. Guests call it cozy, inspiring, and unforgettable — a stay that feels like an experience, not just a place to sleep. Nestled in the First-on-the-Hill neighborhood off Century Drive, the Dome is perfectly positioned for everything Bend has to offer. Whether you’re here for skiing, biking, hiking, or just relaxing, you’ll love how close you are to Bend’s best adventures.

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.

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.

Family/Remote Work Friendly House in Bend OR

Welcome to the "Cascade Chalet", perfect for a family or friend's getaway. Relax in the tranquil backyard while the ponderosa pines whisper above. At night, enjoy the warm fire, while gazing at the constellations under a cozy blanket. You're 30 minutes from Mt. Bachelor, 8 minutes to Phil's Trailhead and walkable to downtown. The back door leads to a spacious yard with plenty of seating and a large outdoor green space, grill, gas fireplace and kids play area.

<SALE> Cozy River Front "NEST" | Old Mill | Dog |

Enjoy this Luxury 2nd level apartment directly on the Deschutes River. Easy trail access is steps away where you can run/hike the 3 1/2 mile loop or paddle up and down the river. Back at home sit on your deck and listen to the sounds of the river going by. The Old Mill, Box Factory, Food Carts and more are a peaceful 3/4 mile stroll along the river trail ....yet you are a world away in your "Nest" within the Ponderosa Pines along the river. ** Enjoy! **

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.

Adorable West Side Cottage, Pet Friendly!

Enjoy a cozy and comfortable stay in my 1-bedroom, 2-bathroom home, complete with a bonus room that offers plenty of privacy when needed and a plush futon that allows for two additional guests (best for up to 3 adults or 2 adults and 2 kids, or two couples would work as a well ) Conveniently located within walking distance of Newport Market, Backporch Coffee, Chow, and Spork, it's just five blocks from downtown