Guesthouse vacation rentals in Deschutes County

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Deschutes County

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

The open-concept kitchen and living area feature a long wooden countertop with seating for six. A gas stove, under-counter appliances, and a stylish backsplash enhance the space. Two cozy chairs provide seating, with natural light filtering through the nearby window.

Guesthouse in Bend

4.97 out of 5 average rating, 263 reviews

Midtown gem I Cozy Fire I Full kitchen I Park View

Above garage one bedroom/one bath apartment in booming midtown. Open living with a gas fireplace, ac, full-sized kitchen, and gas stove. A large bathroom with a deep tub to relax or let the kids play. The bedroom features a cozy queen bed with a new Tempur-Pedic mattress topper and ample closet space. The east-facing deck is ready to sip your morning coffee while you wake up slowly, grill for an evening in or sit and work with the high-speed wireless as you watch the dog park across the street!

Top guest favorite

A winding wooden pathway is showcased, leading through a natural landscape. Native shrubs and greenery surround the path, enhancing the connection to the outdoors. The boardwalk is constructed of smooth wooden planks, inviting exploration of the surrounding environment.

Guesthouse in Bend

4.99 out of 5 average rating, 117 reviews

Renovated Condo - Ideal Location

This is Central Oregon's premier location for recreation activities. Your stay at this sleek condo will have you encircled by peaks, lakes, meadows, culture, adventure, breweries, festivals, family fun and more. Offering a cozy condo that comfortably sleeps 2 guests with a queen size bed, a mini kitchen, the convenience of on-site laundry facilities. Plus, a living/dining are comforts that would be hard to find in an average hotel. Come make this your launching pad as you experience Bend!

Top guest favorite

A serene view of a calm canal is presented, surrounded by lush greenery and trees. Smooth rocks form a pathway leading toward the water, reflecting the clear sky above. Small bushes dot the landscape, enhancing the natural, tranquil setting.

Guesthouse in Bend

4.99 out of 5 average rating, 118 reviews

NEW Tranquil Retreat On Canal

Charming, clean, comfortable, fully renovated guest house on 3 acres, nestled by a canal. A quiet escape near Pine Nursery Park, just 5 miles from downtown and less than 20 minutes from the airport. Enjoy beautiful natural light, vaulted ceilings, large bathtub, and balcony with outdoor seating and a beautiful view. Fully stocked kitchen, washer & dryer, heat & AC, blackout shades, board games, books, amenities for kids, smart TV, and a Blu-ray player for rentals from The Last Blockbuster.

Top guest favorite

Guesthouse in Bend

4.98 out of 5 average rating, 409 reviews

Bend Ranch Guesthouse on 20 acres

Enjoy our private/detached guesthouse and wake up surrounded by nature on a 20 acre property bordered by farms and views of the Sisters Mountains. Excellent WIFI. Featuring wedding venue, Sage & Honey Spa, tube/lifejacket rentals. On the 2nd floor, 1 king bed, 1 queen bed, queen sofa bed, Full kitchen, refrigerator, dishwasher, microwave, hot plate, toaster oven, Keuirg. 17min to downtown Bend, 12min to downtown Redmond/Airport, 35min to Mt. Bachelor, 30mins to Sisters, 10mins to Tumalo.

Top guest favorite

The entrance features a vibrant coral door framed by stone accents, leading into the guest house. A small welcome mat is placed before the door. Red Adirondack chairs are positioned nearby, and green and gray plants add a natural touch to the patio area.

Guesthouse in Terrebonne

4.98 out of 5 average rating, 162 reviews

Modern lofted guest house

Enjoy our recently completed lofted guest house. Just 3.7 miles from smith rocks and walking distance to Terrebonne restaurants, coffee and local grocery store. Centrally located, 15 min to the airport and just a 30 min drive to Bend. Our guest house has a fully stocked kitchenette ( NO OVEN) with a toaster oven/air fryer, and an induction cook top. Sit back and relax outside in the Adirondack chairs while drinking a Nespresso coffee. Wifi is provided as well as a Roku T.V and DVD.

Guest favorite

A kitchenette is presented, featuring wooden cabinetry and a granite countertop. Essential appliances include a microwave, coffee maker, and a blender. A black sink is situated next to a small fridge, with additional storage for kitchen items visible in the pantry area.

Guesthouse in Bend

4.93 out of 5 average rating, 196 reviews

Private Studio w/ Hot Tub near the Deschutes River

The Fresca Studio has a kitchenette, hot tub, BBQ & bikes. Downtown Bend is a few miles away, McKay cottage, Deschutes River Trail & Sawyer park are a short walk, and all things Bend eat, drink, biking, hiking, skiing are all close by. The studio is separate from the main house w/ a private entry & patio, fully furnished, and easy access to/from the highway and parkway. Not suitable for children under 5y/o, 2 guests only and children are considered guests. No pets. See you soon!

Top guest favorite

A serene stream flows gently through a wooded area, flanked by lush greenery and tall trees. The water reflects the surrounding nature, creating a calming atmosphere. Branches extend over the water, enhancing the natural landscape.

Guesthouse in Bend

4.95 out of 5 average rating, 205 reviews

NFF Cottage with Cascade Mountain Views

Behind a gated entry, this cottage is a prime location between Bend & Sisters. It offers two parking spaces, with additional room for a car or trailer if needed. Guests are welcome to bring equipment for exploring Central Oregon, such as tubes, kayaks, paddle, skis, snowboards, and bikes, all of which can be conveniently stored in a private storage shed within the fenced yard. This delightful cottage is situated on our working family farm, home to a variety of friendly animals.

Guest favorite

A curly-coated dog is positioned at a weathered picnic table, focused on a small pinecone resting on the surface. The background features a hint of grass and part of a building, suggesting a casual outdoor environment.

Guesthouse in Bend

4.92 out of 5 average rating, 181 reviews

The Outpost Bend

The Outpost is a seperate guest home located on our 10 acre hobby farm. It offers spectacular views of the Cascades, stunning sunsets and a peaceful, private location 15 minutes east of downtown Bend. The property adjoins public land, and is on a quiet country road. Our family lives onsite with our 3 sons, dogs, hens, and sheep. The Outpost has a private driveway, use of basketball court, and a lovely private outdoor seating area. 45 min drive to Mt. Bachelor.

Guest favorite

A keypad entry system is mounted on a wooden post, featuring clearly labeled buttons for access. In the background, trees and a gravel path are visible, indicating a serene outdoor setting.

Guesthouse in Bend

4.93 out of 5 average rating, 368 reviews

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.

Top guest favorite

The entrance features large glass double doors framed by black trim, providing a modern touch. Two stylish outdoor lights are mounted above planters with greenery on either side of the entryway, complementing the clean lines of the cottage's exterior.

Guesthouse in Redmond

4.98 out of 5 average rating, 256 reviews

Modern Downtown Cottage near Outdoor Adventure

Nestled in the heart of Downtown Redmond, this beautifully designed cottage offers the perfect blend of convenience and comfort. You'll find yourself within walking distance of charming coffee shops and restaurants, and just 14 minutes away from the breathtaking Smith Rock. The Redmond Airport is less than 10 minutes away, and if you're planning a visit to Bend, you can be downtown or floating on the Deschutes River in under 20 minutes.

Top guest favorite

An open living area showcases a spacious bed against a window with natural light, a leather seating arrangement, and a dark wood dining table. A wooden ceiling with exposed beams adds character. Plants are suspended from the ceiling, enhancing the indoor greenery.

Guesthouse in Bend

4.99 out of 5 average rating, 651 reviews

Botanical Studio in the Trees - Steps to Trails

Wake up to treetop views at this spacious bungalow peppered with live plants, unique art, and a stunning cedar ceiling. Stroll down to the Deschutes River Trail, which can take you downtown. Enjoy the locals-favorite First Street Rapids Park, then curl up and restore on the ultra comfy king bed. Creature comforts abound! No pets please. Trip insurance recommended if illness, weather or smoke may be an issue.

Superhost

The exterior of Kingston Kottage is framed by tall pine trees, showcasing a charming entrance with a wooden door sheltered by a decorative overhang. A clear walkway leads to the entrance, flanked by colorful fall foliage and low-maintenance landscaping.

Guesthouse in Bend

4.91 out of 5 average rating, 175 reviews

Kingston Kottage

Kingston Kottage is conveniently located in the heart of Bend's popular west side. Just a 5-10 minute walk from some of Bend's best restaurants and breweries and a 15-minute walk or 5-minute bike ride to downtown Bend. Super private, clean, comfortable, and quiet! The Kottage is available for a minimum rental period of 30-days. perfect for an extended visit to Bend.