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.

<SALE> River Front | Hot Tub | Old Mill | Dogs

Enjoy this Contemporary Luxury Home directly on the Deschutes River. Literally step out your back door and stroll, run or paddle up and down the river. The river trail is a 3 3/4 mile loop and one of the best hikes around. Back at home sit on your deck or in the Hot Tub and listen the the sounds of the river going by and enjoy peaceful solitude. Shop or get a bite to eat at The Old Mill, Box Factory, Food Carts and more which are a peaceful 3/4 mile stroll along the river trail. Enjoy!

Minutes to Bachelor! Spa. Fire pit. Ski!

Welcome to Hummingbird House, your Bend home away from home! This beautiful three bedroom plus den home is sure to become a vacation favorite for you and your family! Located within the Deschutes National Forest, these are the closest homes to Mt. Bachelor and just ten minutes to town. An outdoor patio area features a hot tub, fire table and dining table perfect for hanging out after a long day exploring Bend. The Deschutes River Trailhead is only a few steps from the back door. Book today!

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.

The Blackberry Cottage

This adorable 1950's cottage is located in the heart of Midtown Bend, within walking distance to local coffee shops, restaurants, parks and Pilot Butte State Park, and less than a mile away from downtown Bend. Two light-filled bedrooms both have double French doors leading out to a large back deck and a fenced, private backyard. A cozy living room, and eat in kitchen make this home the perfect place for a small family or a few friends to share. Serene fenced back yard space with hot tub.

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!

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.

Craftsman Style Retreat in Bend River West

Located in one of Bend’s most walkable neighborhoods, this studio is a couple blocks away from Columbia Park with easy walking access to Drake Park, Harmon Park, McKay Park and the Old Mill District (and amphitheater). After (or before) you’ve explored nearby shopping and food, head out and explore the endless outdoor activities such as skiing, Mt. Biking, rafting, fishing, and much more! You are short pedal to Phils Trails, a 5 min walk to Mt. Bachelor’s Park n Ride (or 25 min. drive).

Cabin on The Rim

Take it easy at this unique and private getaway. This off the grid studio cabin is located just 10 minutes from Smith Rock and 10 minutes from Lake Billy Chinook. It is positioned on the edge of the Crooked River Gorge with breathtaking views of the canyon. Near the cabin is a trail head to a private hiking trail that takes the adventurer down into the canyon where the scenery is otherworldly. Enjoy a sunset with full cascade Mountain View’s, green pastures, and grazing horses.

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.