Holiday houses in Pilot Butte

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.

River Run Bend Bungalow & Romantic Spa Grotto

Relaxing, private spa & sauna grotto is ready for your romantic Bend getaway! This quiet, wooded, centrally located standalone bungalow is steps from the Deschutes River trail and within easy walking distance of 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!

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.

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.

NEW Tranquil Retreat On Canal

Charming, clean, comfortable, fully renovated guest house on 3 acres, nestled by a canal. A quiet escape near Pine Nursery Park, just 5 miles from downtown and less than 20 minutes from the airport. Enjoy beautiful natural light, vaulted ceilings, large bathtub, and balcony with outdoor seating and a beautiful view. Fully stocked kitchen, washer & dryer, heat & AC, blackout shades, board games, books, amenities for kids, smart TV, and a Blu-ray player for rentals from The Last Blockbuster.

Petite Suite: Midtown Warm & Welcoming This Winter

Welcome to our charming suite in the heart of midtown Bend, just 5 blocks from the beautiful Pilot Butte and only 5 minutes from downtown. Our studio apartment is the perfect choice for those looking for a comfortable and convenient home base for their Bend adventures. The location is ideal for exploring all that Bend has to offer. Take a hike on Pilot Butte, or stroll through the charming streets of downtown. You'll find plenty of shops, restaurants, and cafes nearby to enjoy.

Drake @ The DUPE - blocks from Old Mill District -

Drake: Located blocks from the Old Mill District, this beautifully updated 2-bed, 2-bath townhouse blends privacy with an unbeatable location. Walk or bike to the Old Mill, Deschutes River, dining, and the Hayden Homes Amphitheater. Tucked in a serene, tree-lined setting, the private home features a bright kitchen with updated appliances, a primary suite with a walk-in tile shower, and a separate porch with a BBQ grill. The perfect mix of modern comfort and convenience.

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.

The Grove - King Beds & Hot Tub - No pets

Adorned with murals of forests, our Airbnb invites you to immerse yourself in nature's embrace. Relax on the sunken patio surrounded by live plants, or unwind in the private hot tub under the stars. Inside, enjoy cozy amenities including a fully-equipped kitchenette and luxury linens. Our hideaway promises an enchanting experience you won't forget. Book now and let the magic unfold! Please read the entire listing for details on potential for noise.

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.

Midtown Home - 5 min from Downtown

Welcome to our home in Bend, OR! Our cozy, newly renovated midcentury modern home is centrally located in charming Midtown Bend. Enjoy a bonfire in the backyard, or relax after a day on the mountain in the elevated living area. Take a stroll with your pup down to Hollinshead Park to enjoy the trees and beauty of the neighborhoods. We are conveniently located: 5 Minutes to Downtown Bend 7 Minutes to Old Mill District 35 Minutes to Mt. Bachelor

Downtown - Super Walkable - King - Local Hosts

Stay in a rare home in the heart of downtown—a beautifully restored 1922 craftsman with warm wood, plants, vaulted ceilings, and natural light. Enjoy charming architecture and local artwork. Walk to dozens of restaurants, breweries, coffee shops, and stores. Cross the alley to food trucks and live music, or relax in your private walled courtyard with native plants. We keep a clean, low-allergen home with no pets and no scented products.