Holiday rentals with a fireplace in Bend

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!

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.

FLOAT THE RIVER! River, Beach Access Downtown Bend

Welcome to our 1918 Bungalow on Riverfront Street. This simple, no frills one bedroom, one bath sleeps two to three. Enjoy a fully equipped kitchen, floor to ceiling river rock gas fireplace, inviting front porch, back deck with propane BBQ, table/ chairs. The Bungalow has a peek of the river, as it is considered the "guest house" to the larger "main house" it shares the lot with. Enjoy low bank river access to launch your kayak. Park the car and experience the best Bend has to offer.

Serenity Retreat | Pool, Spa, Trails & Mt Bachelor

Situated in the serene Mt Bachelor Village, our home is a harmonious blend of seclusion & natural charm. Encircled by a lush landscape & towering trees, it serves as a tranquil retreat, perfect for relaxation. The property is just a short distance from Bend's lively amenities, offering access to both outdoor adventures & urban pleasures. This residence is an ideal choice for those wishing to enjoy the tranquility of nature while being conveniently close to the city's attractions.

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.

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.

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.

Adventure Awaits! Walk to downtown and river!

A perfect home base for all your adventures in Bend! Just a 10 minute walk from downtown. Walk or bike to the best restaurants and breweries in Bend. Swimming, hiking, and fishing in the Deschutes river steps from your doorway. King Bed~ Gas fireplace ~ Reading nook ~ Comfy queen sleeper sofa ~ Air Conditioning ~ Games ~ 2 TVs ~ Full kitchen ~ 2 balconies ~ Keyless Entry ~ Shared laundry room ~ 2 Bathrooms ~ K Cup coffee bar ~ Private WiFi ~ Roku TVs

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.

Mid Towns NEW modern private guesthouse

The Mid Town Majesty house is our cozy little detached guesthouse located in a quiet residential neighborhood. A brand new build thoughtfully designed with stylish mid century modern finishes throughout the house. Plenty of off street parking right in front of the home. You are a short drive to downtown, Old Mill District and grocery stores. Walking distance to Mid Town Yacht Club which has Bends finest food trucks.

The Land of Aus

The Land of Aus is your quick ticket to relaxation. This charming rustic mountain home is less than a 5 minute walk from the Deschutes river and has everything you need to find solitude and tranquility. Amenities to help you unwind include a hot tub with delightful canal views, a cozy fireplace, clawfoot tub and a Finnish sauna to help sooth those muscles after a long day in the Central Oregon Outdoors.

Bend Waterfront Home: Hot Tub, Walk to Town

Waterfront Luxury in Downtown Bend w/ Private Hot Tub & River Access Indulge in waterfront bliss on Mirror Pond. Soak under the stars in the brand-new private hot tub, launch paddle boards directly from the backyard, or take a 5-minute stroll to downtown Bend’s top breweries and restaurants. Perfectly tailored for mountain adventures, river days, and relaxing group retreats. License Number: STR-18-1015