House holiday rentals in Deschutes River Woods

The modern exterior of the ADU features wooden accents and large windows, surrounded by lush greenery. A small outdoor seating area with two chairs and a fire pit is visible. The entrance is framed by a wooden fence, providing privacy and inviting atmosphere.

4.99 out of 5 average rating, 205 reviews

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.

The exterior of a modern home is framed by blooming trees and shrubs, showcasing a gray exterior with large windows. A decorative pathway leads to the entrance, which features a covered porch. The driveway is spacious, providing easy access.

4.98 out of 5 average rating, 548 reviews

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!

A spacious living area features solid oak flooring and a wood-burning stove set against a stone wall. Large windows offer views of the surrounding trees and snowy landscape, while a cozy stack of firewood is arranged beside the stove.

5 out of 5 average rating, 189 reviews

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.

A well-lit dining area features a long table surrounded by tall chairs, with cushions in warm tones. A modern light fixture hangs above, while natural light shines through skylights and large windows, highlighting a decorative wall piece and a workspace nearby.

4.99 out of 5 average rating, 156 reviews

Quail Park Haven in NW! King Beds & Hot Tub

Relax in this peaceful NW Bend home with king beds and access to Quail Park. Enjoy natural light from the skylights and high ceilings. Kick back in the expansive backyard with mature plantings, tall trees and flagstone paths. Multiple patios including a deck off the living room, a paver patio with fire-pit, hot tub, outdoor furniture and gas BBQ. EV charger, HEPA air filter and garage access. No parties or pets please. Trip insurance recommended if illness, weather or smoke may be an issue.

The exterior of the two-story cabin features a charming combination of wood and siding. A welcoming porch with seating is visible, framed by manicured landscaping. Above, a private balcony invites relaxation, showcasing the property’s connection to the surrounding natural beauty.

5 out of 5 average rating, 282 reviews

Mountain Bliss: Gateway to Mt. Bachelor and More

When the mountains are calling, Bend is like nothing on earth. Savor the charms of Base Camp throughout the year in this luxurious and spacious cabin (1200 square feet). Celebrate the great outdoors – best experienced through unparalleled adventures at Mt. Bachelor (18 miles), Phil’s trailhead (15 minutes), the Deschutes River (5 minutes) as well as the endless access to hiking, biking, running trails, skiing, golf, breweries, restaurants, coffee shops, and the Hayden Homes Amphitheater.

A modern living room features large windows that provide views of the outdoors. A gray sectional sofa and a bright orange chair are arranged around a light area rug. A wooden coffee table is positioned nearby, and a TV is mounted on the wall. A stove adds a touch of warmth to the space.

4.99 out of 5 average rating, 184 reviews

Modern high-end home, walk downtown

This fantastic modern home is in the sweet spot of Bend...just next door to the Deschutes River, Downtown Bend, parks, restaurants and dining, nightlife, and family-friendly activities. You'll love our home because of the amazing location, the mid-century inspired ambiance, the high ceilings, the people, and the local views. We are the perfect centrally located home for any Bend adventure. Our place is great for couples and solo adventurers. This is not a party house. Sorry no pets.

A spacious living room features a light-colored sectional sofa positioned around a glass coffee table. Large windows invite natural light, revealing a view of the outdoors. A stone fireplace provides a warm focal point, complemented by a cozy armchair and decorative elements throughout.

4.99 out of 5 average rating, 187 reviews

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.

The spacious living area features contemporary furniture with a striking orange sofa and cozy armchairs surrounding a central coffee table. Large windows allow ample natural light, highlighting the open layout and views of the outdoor greenery. Pendant lighting and wooden beams add warmth to the modern design.

4.95 out of 5 average rating, 137 reviews

Pet Friendly! Hot Tub, River Trail, Bachelor

Welcome to your modern mountain oasis, that rare property you stumble upon that’s likely to check almost every box on your list of must-haves along with plenty of extras. Here’s a quick glance at some the highlights: - Minutes from Old Mill District - Close to skiing/hiking/biking, with Bachelor, river, and lakes all nearby. - Spacious Bedrooms, Bathrooms and Modern Stocked Kitchen - 2 person mini hot tub - Fast Wifi + Smart TVs - Board games, Books & more

5 out of 5 average rating, 182 reviews

A light-filled living area features a black leather sofa and a wooden armchair facing a large window. A patterned area rug adds warmth to the hardwood floor. Barstools are placed at the kitchen counter, and artwork is displayed on the white wall.

Home in Larkspur

Curated Comfort | Quiet, Clean, Beautiful Design

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 Bend Fire & Rescue. We love books, music, and helping you discover the best of Bend - trails, eats, and community.

A northwest style house is nestled among tall ponderosa pine trees. The front features welcoming wooden accents, a large stacked firewood pile, and an attached garage. Natural grasses are scattered across the landscaped area, providing a rustic charm to the peaceful setting.

4.94 out of 5 average rating, 232 reviews

☆ Quiet Forest Retreat | 10min from Old Mill ☆

This custom 21st century northwest style house is on a quiet dead end road above the Deschutes River about a 10min drive to Old Mill, surrounded by ponderosa pine trees. This premium house has tasteful decor and gorgeous wood accents. Natural light streams in from the wall of windows in the great room. The house features a full open kitchen with concrete counter tops, a large wood burning fireplace, hardwood floors, and a spacious deck.

A well-appointed bedroom features a spacious bed draped in striped bedding. Two bedside lamps provide soft illumination on either side, while a large window offers views of the outdoor greenery. A full-length mirror adds functionality to the room's clean design.

4.98 out of 5 average rating, 167 reviews

Best for Old Mill:River Trail, Views & Town

Awesome location! Fast internet, Wi-Fi. Clean and close to everything that is great in Bend - the river, Mt. Bachelor, restaurants, nightlife, cycling, kayaking, paddle boarding, hiking, breweries, concerts and so much more. You’ll love the location, ambiance, the outdoor space, and the comfy bed. Walk along the river trail to experience what everyone loves about Bend. Easy drive to Mt. Bachelor, approximately 25 minutes.

The exterior of the home features a welcoming front porch with two black Adirondack chairs and a small table. A path leads to the front door, bordered by low-maintenance landscaping and a natural stone feature. Large windows provide views of the surrounding area.

4.99 out of 5 average rating, 304 reviews

Your gateway to Mt Bachelor & all that Bend offers

You're invited to stay at Kart Haus, located in the River Camp development on Bend's west side. Located in the middle of an outdoor recreational heaven: Kart Haus is 20 minutes from Mt. Bachelor's slopes and surrounding trails and just steps to the Deschutes River Trail, an oasis for walking, running and biking. Year-round, you're a short drive from downtown, the Old Mill District, tasty eateries, cafes and brewpubs.

Popular amenities for house rentals in Deschutes River Woods

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The living room features a stone fireplace surrounded by wooden shelves, with a large flat-screen TV mounted above. A rustic wooden coffee table sits on a patterned area rug, complemented by leather seating and large windows that allow natural light to flood the space.

4.98 out of 5 average rating, 126 reviews

Sunriver Luxury Family Home at Caldera Springs

The single-story home features a natural wood exterior surrounded by tall trees. A spacious front deck includes a dining table with an umbrella and two chairs, providing a welcoming outdoor seating area. The driveway leads to a two-car garage.

4.8 out of 5 average rating, 185 reviews

Sunriver Home; Hot Tub, SHARC, Fireplace and More!

A spacious living area features a high ceiling with wooden beams, enhancing the sense of openness. A modern sectional sofa is arranged around a central coffee table. Natural light floods through a large window, while a cozy seating nook with stylish decor and a fireplace adds warmth to the space.

4.96 out of 5 average rating, 114 reviews

The Birch Abode: Spacious & Serene-Sleeps 8 +SHARC

The exterior of the house is presented, surrounded by tall trees and foliage. A large paver patio is visible, featuring a barbecue and outdoor seating arrangements, all bathed in the warm hues of a sunset.

4.92 out of 5 average rating, 178 reviews

Spacious 7BR Getaway, Golf View & Waterpark

The open living space features a high beamed ceiling and natural wood accents. Two leather sofas are arranged around a light-colored coffee table. A dining area with a wooden table sits adjacent to the kitchen, which displays modern appliances and bar seating.

4.94 out of 5 average rating, 261 reviews

A Little Peace of Paradise, A/C & 8 SHARC Passes

A spacious living area features wooden ceilings and large windows, allowing natural light to enhance the room. Comfortable seating is arranged around a central coffee table, while sliding glass doors open to a deck framed by views of the surrounding landscape.

4.95 out of 5 average rating, 177 reviews

Dog-Friendly Home w/ Hot tub and 10 SHARC passes

4.98 out of 5 average rating, 101 reviews

3K ft² | MtBachelor | Hot Tub | Arcade | Ping Pong

The exterior of the cabin is shown, featuring a sloped roof and welcoming front porch. Surrounded by trees, the landscaped front yard includes green grass and shrubs, creating a serene atmosphere. A gravel pathway leads up to the entrance, emphasizing the cabin's inviting presence.

4.94 out of 5 average rating, 145 reviews

3BR/3BA | Hot Tub +SHARC +AC +Pool Table+Ping Pong

Weekly house rentals

4.94 out of 5 average rating, 106 reviews

Two blue Adirondack chairs are positioned on a lush green lawn, overlooking the calm Little Deschutes River. In the background, the river reflects the surrounding trees and grassy areas under a clear sky, creating a serene outdoor space for relaxation.

Home in La Pine

Riverfront/Hot Tub/Dock/Pet Friendly/Game Room

An inviting outdoor seating area features a modern fire pit surrounded by cushioned chairs, offering a cozy spot for gathering. A dining table is set for outdoor meals, and thoughtful lighting enhances the space under the covered patio, framed by lush trees.

5 out of 5 average rating, 111 reviews

Family/Remote Work Friendly House in Bend OR

A quaint cottage exterior is surrounded by greenery, featuring a covered porch with steps leading to the front door. Vibrant landscaping includes flowering plants, bushes, and trees, enhancing the inviting atmosphere of the home.

4.94 out of 5 average rating, 435 reviews

Cozy, Pet Friendly, Hot Tub. Garage.

The cozy bedroom features a rustic wooden bed frame with soft linens, complemented by natural light from a nearby window. A stylish soaking tub is presented with a wooden shelf nearby. The kitchen showcases modern appliances with a striking blue cabinetry, while a snowy mountain landscape is displayed outdoors.

4.96 out of 5 average rating, 219 reviews

Romantic Farmhouse near Mt. Bachelor

4.98 out of 5 average rating, 306 reviews

Home in Orchard District

Have a Patio Barbecue at a Pet-Friendly House in Midtown

An outdoor deck features a hot tub and a shaded seating area, surrounded by potted greenery. A table with an umbrella is positioned nearby, alongside comfortable chairs, creating a space for relaxation or dining. The deck's two levels are connected by stairs.

4.96 out of 5 average rating, 149 reviews

Modern home in NW Bend (w/HOT TUB!) Walk to Shops!

Superhost

Home in Old Bend

4.81 out of 5 average rating, 422 reviews

Downtown Den

4.95 out of 5 average rating, 119 reviews

Home in Orchard District

Remodeled Gem of Midtown

Private house rentals

4.96 out of 5 average rating, 192 reviews

A comfortable living area features a grey sofa and two wooden armchairs, arranged around a rectangular coffee table. A brick fireplace with decorative items rests on the wall. Natural light enters from a nearby window, and a door leads outside.

Home in Old Bend

Franklin Flat - House @ Downtown & Historic Dist

A charming outdoor space is featured, characterized by a gravel pathway bordered by greenery and plants. A wooden bench is positioned nearby, providing a peaceful spot to enjoy the natural surroundings. The property is enveloped by tall trees, enhancing the tranquil atmosphere.

5 out of 5 average rating, 9 reviews

Ponderosa Pine Oasis on 1 acre in BEND

The cabin's exterior is crafted with natural wood and features large, angular windows that showcase the surrounding forest. A spacious deck with Adirondack chairs extends across the front, inviting relaxation and connection with nature.

4.98 out of 5 average rating, 166 reviews

Private Luxury w/Hot Tub on Pvt Lake Amazing Views

A theatre room is observed, featuring a large projection screen and a cozy seating arrangement with recliners. Windows allow natural light, while decorative curtains provide privacy. The room is equipped with audio-visual equipment, enhancing the movie-watching experience.

4.86 out of 5 average rating, 248 reviews

OldMilOasis,Theatre,HotTubSauna,Gym,BrickPizzaOven

A welcoming great room showcases a spacious light-colored sectional sofa adorned with accent pillows, positioned around a round coffee table. A stone fireplace adds warmth, while a flat-screen TV is mounted on the wall. Natural light filters through the windows, illuminating the vibrant area rug.

4.91 out of 5 average rating, 139 reviews

DogOk. Large Retreat, 3 King Beds. Fire pit

5 out of 5 average rating, 6 reviews

Widgi Creek Retreat

An inviting dining area features a natural wood table complemented by sleek metal bench seating and chairs. Bright light fills the room, highlighting the open layout that connects to the living area, where a cozy fireplace can be seen in the background.

4.96 out of 5 average rating, 28 reviews

New, Stunning & Modern Luxury Retreat

A spacious game room features a foosball table in the foreground, surrounded by light-colored carpet. Two large windows allow natural light to illuminate the room, creating a bright atmosphere. A gray sofa is positioned against the wall, complemented by an indoor plant and a piece of wall art.