Family-friendly holiday rentals in Deschutes River Woods

Chukar's Nest/Old Mill Dist/Hot Tub/BBQ/Firepit

Chukar's Nest is located only six blocks from the Old Mill District, Deschutes River, Riverbend & Farewell Bend parks. Our 1-level, 1459 SF custom home built in 2005 offers a great room floorplan, hardwood floors throughout, living room w/ gas fireplace, dining room w/ seating for 6, and a fully stocked kitchen w/ island seating & newer appliances. The bedrooms have memory foam mattresses & luxury linens. The hall bookshelf has a plethora of good books, puzzles, and games for adults and kids.

Theater Room w/Movies, Netflix, Amazon Prime

The house sits on 2 1/2 acres of beautifully landscaped property with 3 ponds and 33,000 Sq feet of lawn. Private entrance to guest suite, quiet area with like properties surrounding. Located in the northeast section of Bend. Owners quarters are located in an ADU attached to one end of the house in a separate area allowing complete privacy. There is a children's play area and trampoline. The area has numerous parks,hiking trails, rivers, skiing, lakes and is the gateway to the Cascade mountains.

Views & Sounds of Deschutes River in Downtown Bend

Entire one bedroom apartment with private entrance from extra large elevated deck with BBQ. Enjoy the view and calming natural sound of the Deschutes River running over the spillway 300 feet away. Easy and secure bike/ski storage. The apartment is a four minute walk to downtown Bend where there are many great restaurants, bars, boutique shopping. You won't find a better location to explore Bend. Electronic locks for easy check-in. Enhanced cleaning procedures. Licensed by the City of Bend.

Home in Lodges at Bachelor View - Book Now!

Enjoy Bend’s newest west-side neighborhood nestled beside Century Drive, the gateway to Mt. Bachelor and the Cascade Lakes. Our unique location puts you right on the connector trails to the popular Phil's Trail System for mountain biking or casually strolling along the Deschutes river trail. With access to the National Forest in just steps and breweries mere minutes down the road, Pinehaven is as 'Bend' as it gets. Thank you for considering Pinehaven for your stay. We think you’ll love it here!

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.

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.

Jewel Box Bend-Quaint private downstairs apartment

Come relax in our one bedroom completely private downstairs unit with separate entrance. Enjoy the fresh air and quiet tree-lined streets of one of Bend’s older neighborhoods. We are walking distance to Brookswood Plaza and just a quick 5 minute drive to the Old Mill District, the Deschutes River and less than 10 minutes into Downtown Bend. Fully stocked kitchenette (no oven or freezer). Fold out futon style couch for additional guests. On-site driveway parking and additional street parking.

Cozy Studio! Walk to NW Crossing and Shevlin Park

Cozy, soft decor fill this light, bright studio with a private entrance. Shevlin Park and Phil's Trail are minutes away for hiking, running, and mountain biking. Mt. Bachelor is a short 30 minute drive for skiing in the winter and downhill biking in the summer. Smith Rock is a 45 minute drive for hiking and climbing enthusiasts. Shopping and dining are within walking distance at NW Crossing or a a short drive to the Old Mill or Downtown Bend. Mesh Network Wifi, coffee, tea and snacks provided.

The Big Tiny

Reset and rejuvenate at the Big Tiny. Our thoughtfully designed, unique tiny house is fully equipped for your comfort and is surrounded with gorgeous desert views, and is also pet friendly. Conveniently located just 15 mins from downtown Bend. Enjoy all that Central Oregon has to offer. Start your days sipping coffee in the front yard while drinking in the fresh air. Relax after a day of adventure under the starry sky with a local beer or glass of wine next to the propane fire pit.

Tall Pine Tuckaway! Hot tub, EV charge, RV hookup

Welcome to Tall Pine Tuckaway! This sprawling home sits among the peaceful wooded edge of town yet is just a 10-minute drive to Downtown Bend! Perfect for large families or groups, this home has it all - salt water hot tub, firepit patio, landscaped acreage for kids and pets to play, universal EV charger, two living rooms, dedicated office with lightning-fast 1G wifi, and full RV hookups! Bring your trailer and toys and ride directly onto China Hat Road for some excellent off-roading.

Closest to Bachelor. 8 min to town. Spa. DogsOk!

Gorgeous home, located steps from the Seventh Mountain Resort and the Deschutes River Trailhead. Luxuriously appointed with Casper Mattresses. Fully equipped chef's kitchen with All Clad cookware, KitchenAid, and much more! These are the closest homes to Mt. Bachelor meaning you can easily beat the crowds. This is the perfect place for a friends or family retreat. After a day of activities, take a relaxing hot tub or hang out around the fire outside. Book your vacation today!

Bend Basecamp | 2BR, King Bed, Garage, Fast WiFi

King bed in primary, super fast internet, both rooms with en suite baths & 100% cotton 400 thread count sheets. The perfect home base for your Central Oregon adventures! The primary has a comfy king bed & bathroom. The 2nd bedroom has a bunk (full mattress on the bottom, and a single up top) with its own bathroom. Main level features a spacious LR, DR & Kit along w/ a 1/2 bath. Located in the Boyd Acres neighborhood, just minutes to downtown and everything Bend has to offer.