Vacation rentals with outdoor seating in Deschutes River Woods

Guest suite in Northwest Crossing

A spacious living area features two comfortable armchairs and a cozy couch, accompanied by a wooden coffee table. A rug adds texture to the floor. Natural light enters from the windows, illuminating the inviting atmosphere of the room.

4.87 out of 5 average rating, 467 reviews

Great location! Highly rated by guests.

You'll feel like you've rented a small house with your own private kitchenette, fridge, living room, bath, walk-in-closet and washer/dryer. Located in the desirable westside of Bend, walking distance to the popular Northwest Crossing and Galveston restaurants and shopping. Bike straight to Phil's Trails and just a 30 min drive to Mt. Bachelor. Enjoy walking trails just outside the house. Most guests comment that the place is much bigger and more private than they thought. Read our reviews!

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, 537 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!

Superhost

A cozy nook is featured with two comfortable chairs facing a small table, illuminated by natural light from nearby windows. A staircase leads to the lofts above, while the bathroom area is visible in the background, creating a functional and inviting living space.

Tiny home in Bend

4.9 out of 5 average rating, 523 reviews

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.

4.93 out of 5 average rating, 120 reviews

A spacious backyard is shown, featuring a well-manicured lawn and a shaded seating area. The modern chalet is visible in the background, with large windows and a stone chimney. A hot tub is positioned nearby, integrating relaxation into the outdoor space.

Chalet in Bend

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

4.9 out of 5 average rating, 381 reviews

A spacious sleeping area features a large bed adorned with a patterned comforter and decorative pillows. Dark curtains frame a window that allows natural light to fill the room. Two nightstands with lamps are positioned on either side of the bed.

Guest suite in Bend

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.

4.95 out of 5 average rating, 511 reviews

Dome in Bend

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.

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, 276 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 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, 188 reviews

Lava Rock Retreat Modern Rustic Home

Escape to this peaceful and private home nestled amongst the Ponderosa pine trees and lava rock. The modern rustic home boasts 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 grilling, relaxing in the hot tub, or sitting around the fire pit.

5 out of 5 average rating, 110 reviews

A cozy bedroom features a spacious bed with a colorful blanket, complemented by wooden accent walls. A wall-mounted flat-screen TV is above a modern electric fireplace. A small table with two chairs is positioned nearby, with a mirror framed in green accentuating the space.

Guest suite in Bend

Sixties Suite Spot

Escape to our cozy, retro suite, a serene haven centrally located near Pine Nursery Park. Enjoy a tranquil retreat with high-quality amenities, dog-friendly comforts, and snowboard/ski storage. With a semi-private yard featuring Adirondack chairs, easy parking, and a vibrant, photo-ready design, it's perfect for relaxation and adventure. We proudly welcome 2SLGBTQIA+ guests, offering a warm, inclusive environment. Discover a blend of charm and convenience at our unique getaway!

The open kitchen and dining area features high wooden ceilings and large windows, allowing ample natural light. A spacious wooden dining table with multiple chairs accommodates larger groups. A well-equipped kitchen with modern appliances and wooden cabinetry is visible, enhancing the inviting atmosphere.

4.88 out of 5 average rating, 408 reviews

The House on the River

From the moment you enter the neighborhood, you will enjoy a very private road that is peaceful and tranquil. The neighborhood is full of beautiful trees, birds, and an abundance of deer that roam the area frequently laying in and enjoying the large front yard. Bring the bikes for the kids to enjoy riding in the big circular driveway or through the neighborhood. You can take in the surrounding nature with a walk along the river trail. Licensed. Deschutes County license 1443

4.97 out of 5 average rating, 264 reviews

A modern studio features a spacious bed with crisp white linens, a wooden accent wall, and an electric fireplace below a wall-mounted television. A unique wood table sits atop an area rug, with plants adding a touch of greenery to the warm atmosphere.

Condo in Bend

Sunriver Studio with Pool and Hot Tub

This stylish studio in the heart of Sunriver is newly remodeled with a King bed. Seasonal pool and year round Hot Tub! Just a short walk to a brand new food truck lot with 7 trucks, indoor and outdoor seating and a bar. Fast WiFi, a new Samsung 50” tv signed into Netflix, Hulu, HBO Max and more. 25 minutes to Mt. Bachelor. 25 minutes to downtown Bend. Parking is just a few feet from your door. This super clean condo is perfect for all of your central Oregon adventures.