House holiday rentals in Deschutes County

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.

<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!

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!

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.

Modern Home Close to OLD MILL | HOT TUB! | 6 Bikes

This absolute gem is located in the heart of Bend and is less than 5 minutes from the Old Mill District. Our 3 bed/2.5 bath mountain modern home backs up to the canal and has just about every amenity you could ask for. Such amenities include a private hot tub & back patio, 2 separate living rooms, gourmet fully stocked kitchen, dedicated workspace, high end furniture/artwork, and much more. This home is light and bright with large windows and vaulted ceilings. Come enjoy all Bend has to offer!

Lodge Vibes in the City

Instantly transition into vacation-mode. A modernized 3,200+ square foot log home located within the city of Bend. Enjoy the natural wood surroundings and massive vaulted ceilings that allow for space to spread out and relax. Get your chef on in the fully equipped kitchen or opt for the outdoor BBQ and pizza oven. No parties, pets or ESA's please. Trip insurance recommended if illness, weather or smoke may be an issue. *Note major construction behind the home! Townhome Development in Progress.

Immaculate, Cozy Home in the Heart of Downtown

This gorgeous, welcoming, solar-powered house offers self check-in, speedy WiFi, and complimentary craft beer and coffee. It's located just a couple blocks from downtown, 5 minutes from the airport, 10 minutes from Crooked River Canyon, 15 minutes from Smith Rock, and 20 minutes from Bend. 4 breweries & 3 taprooms are located less than 6 blocks away, and tons of restaurants & shops are close by. Amazing nearby hiking options abound. This space is half of a duplex. No pets or parties allowed.

Stunning mtn Views, sleeps 14, Hot tub, rec passes

Enter the first floor to immediate views of the Cascade Mountain range. The fully-equipped kitchen with Sub-Zero Fridge and gourmet range has direct access to the wrap-around deck, which features an outdoor dining area gas fireplace & gas grill. Upstairs you’ll find the primary suite with king bed with a private balcony boasting views of seven Oregon’s tallest peaks; the bunk room, & queen bedroom. Downstairs is another bedroom, game room, wet bar, 65” TV, & access to the hot tub. Don’t wait!

Bend Country 4 BR/3 Bth, Amazing 9 Mt View, 9 acre

Plan your vacation getaway and escape the destination resorts at our quiet & peaceful lodge home retreat on 9 private acres just north of Bend, "in the country but not far away"; only 10 min. to restaurants & stores if you need anything. Relax while gazing at the amazing 9 Cascade Mts and overlooking a bend of the legendary Deschutes River. Enjoy some of the many Central OR area activities, Skiing, Golfing, Fishing, Hiking, Rock Climbing, Biking, local Wineries & Micro Breweries, & more.

Sisters Peaceful Countryside Home

Located a quick 6 minutes to Sisters and only 15 minutes to Tumalo/Bend, this beautiful, serene ten acre property is perfect for your relaxing getaway. This hidden gem with spacious living areas and rooms, sleeps 6 guests comfortably, and we have provided 3 twin air mattresses for bigger parties. In the morning, enjoy your cup of coffee on our cozy outdoor living patio surrounded by a big beautiful yard and pond. If you're looking for a peaceful vacation, this is the place for you.

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.

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.