Holiday rentals in Deschutes River Woods

Peaceful Hobby Farm, Gateway to Outdoor Adventure

Peaceful, cozy, dog friendly upstairs Apt Hobby Farm Pine tree view KuneKune pigs, Miniature Goats, Brahma chickens & BerneDoodle Pups W/in 25min to Mt Bachelor for winter sports fun 5-10 mins to dog parks, River, theatre, shopping, restaurants depending on what you want to do. New appliances, freshly remodeled, Garage, add parking available  Plush new mattress, comfy pillows a/c, bbq, fire pit 2dog limit small potty area Dog park 10 mins away 2 night min Wi-Fi Paddle boards Queen sofa bed

Lava Rock Retreat Modern Rustic Home

Escape to this peaceful, private home nestled amongst the Ponderosa pine trees and lava rock. The modern rustic home boasts heigh ceilings and a spacious open floor plan with solid oak floors throughout. The kitchen flows into an expansive dining and living area where you can soak in the views of the lava flow, towering pine trees, and visiting deer through the soaring wood framed windows. Enjoy the spacious private backyard while relaxing in the hot tub, sitting around the fire pit, or BBQing.

Forested Artistic Cozy Tiny House w/ Wildlife

This tiny house is quaint and cozy but has all the trappings of a modern home. It has a full size kitchen, bath, dining area, work station, TV loft, and bedroom. We built the house and the surrounding area with the sole purpose in mind to create a perfect, comfortable, memorable getaway in nature. What makes our rental truly unique is the wildlife that roams our property. In the yard you can expect to see deer, birds, squirrels, rabbits, and chipmunks. We are close to town yet away from it all.

Chalet del Sol - Hot Tub - Ping Pong - Fire pit

Welcome to the cozy Chalet del Sol just South of Old Mill District and close to the hiking trails. What this home offers: ☞ Entire property to yourself ☞ Hot tub ☞ BBQ & Blackstone ☞ Ping Pong Table ☞ Master w/king bed upstairs ☞2nd bedroom downstairs queen bed ☞3rd bedroom is a loft w/queen & 2 twins ☞Two full bathrooms ☞ Fast WIFI ☞ Garage ☞ Fully equipped chef’s kitchen ☞ 65” Smart TV w/ Netflix ☞ Lots of Parking → 4 plus cars ☞ Private yard ☞ Washer + dryer ☞ Ductless heating and cooling

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!

Woodhaven 1-Acre Oasis, New Hot tub, Fire Pit

Come out enjoying your own private woods. Large Hot tub, Fire pit and Extra cabin studio. Perfect Blend of City Life and Nature. Nestled on a 1-acre lot at the edge of Bend, you'll enjoy close proximity to city life, ski resorts, and the tranquility of outdoors. *2 bed/ 2 full bath * New hot tub 10k + upgrade * Separate backyard studio -Peaceful workspace/sleeping area * Private ponderosa pines woods * Fire pit * AC * 10 min to Old Mill District * 15 min to downtown * 35 min to Mt. Bachelor

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.

6Br/3Ba The Hopi Getaway-PET Friendly & HotTub

Spacious 16-person single story ranch home with 6 bedrooms (4 kings, 3 queens, bunk bed) and 3 baths. Enjoy an open living/dining/kitchen area, a fun-filled game room, and a large Trex deck patio with a hot tub. Perfect for family and friend gatherings, with plenty of games and space. Pets welcome! Fresh eggs from our chickens and a kid’s play structure add to the fun. Located just 8 minutes from downtown Bend, 10 minutes from Sunriver, and 25 minutes to Mt. Bachelor. DCCA# 793512

Ponderosa Lodge | Bend | Large Yard + Pet Friendly

Picture yourself gathered around the fire pit under the starry sky, sharing stories and roasting marshmallows. The ping pong table adds a fun and competitive element to your downtime, while the wood fireplace sets the perfect ambiance for cozy evenings indoors. For added comfort during warmer months, portable AC units help keep the space cool. And when you're ready to explore, Bend's attractions, from outdoor adventures to dining and shopping, are just minutes away.

Cozy Bend Escape

This cozy SW Bend guesthouse is away from the main house on the property. You’ll feel right at home with all the amenities provided. It sits conveniently down a long driveway for added privacy, and provides a fully-fenced outdoor patio area to relax or let your pup roam. With just a short drive to areas like Old Mill, downtown and Mt. Bachelor, you can explore all Bend has to offer! This guest suite has everything you need to enjoy a weekend (or more) getaway!

Suburban Forest guest house with garage

Experience Bend to the fullest! Adventure is just outside your door with only a few traffic circles between you and the mountains. All of the best eats, drinks, and shopping are within a few miles, and you can store all of your gear in your private garage while you spend time in town. Our home is not suitable for pets or emotional support animals. ESA animals are not considered service animals by AirBnb or the State of Oregon. Please respect this rule.

Urban Craftsman Retreat with Amazing Backyard!

Quiet, relaxing updated home on almost an acre of land in Deshutes River Woods. With the River, Old Mill, Amphitheater, Downtown and Drake park all within 15 minutes you will feel close to it all but be able to enjoy the country feel. A wonderfully appointed kitchen and dining area makes it easy to entertain or simply relax overlooking the expansive yard. Hiking and biking trails are close by to enjoy and Mount Bachelor is a short 35 minutes away.