Guesthouse vacation rentals in Bend

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Top-rated guesthouse rentals in Bend

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

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Top guest favorite

A well-equipped kitchen features dark cabinetry and a light countertop. A coffee maker and electric kettle are positioned beside a lamp on a small table. A window allows natural light to enhance the space, with a colorful rug adding a subtle touch of warmth.

Guesthouse in Bend

4.96 out of 5 average rating, 758 reviews

A Couples Getaway in Old NW Bend

Old Bend meets new Bend in this spacious, newly constructed second level studio apartment in a century old neighborhood in NW Bend. The beautifully appointed room has private access and includes a well accessorized kitchen, comfortable furnishings, a queen size bed, and bathroom. As comfortable as we know you’ll be in the studio, you must get out and experience all Bend has to offer. Hiking, fishing, golf, lakes, rivers, Mt. Bachelor, beautiful sightseeing and many more activities are within a 30 minute drive. We think you’ll enjoy your stay without getting in your car at all. Within blocks you can visit local brew pubs and a great assortment of restaurants and shops. Beautiful downtown Bend is a 15 minute walk, or, a short bike ride on bikes we provide. Experience locally owned restaurants, bars, breweries, unique boutique shops, coffee roasters, bakeries, Drake park and more. This century old neighborhood which was home to many mill workers in the past has become a rejuvenated and vibrant area for a new generation. Many of the old houses continue to be remodeled and, at the same time, retain the old neighborhood feel.

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, 262 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, 114 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!

Guest favorite

Guesthouse in Bend

4.93 out of 5 average rating, 101 reviews

Sound Smith Guesthouse 2\2 - Park Setting

Enjoy SE Bend In this gorgeous brand new space. Beautiful fully furnished 2 bed, 2 bath guest home located adjacent to Larkspur park and Juniper Swim and Fitness where there is a playground as well as trails that go all the way to Pilot Butte. Property has gate access to the park. The lower level of the building is our family business, a guitar/ukulele warehouse with a small office/showroom. Feel free to schedule an appointment to order or check out some of our instruments. SoundSmithGear.com

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, 113 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.

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, 192 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

The image captures a view framed by tall trees, featuring the Cascade Mountains in the background. The clear blue sky highlights the mountain peaks, while the branches of various evergreen trees create a natural border around the scene.

Guesthouse in Bend

5 out of 5 average rating, 257 reviews

Private country escape with mountain views!

Looking for a clean, private getaway in the Central Oregon outdoor wonderland? Five minutes from Pine Nursery Park and Big Sky sports fields, this light-filled, second story space has a private deck where you can enjoy your morning coffee while taking in views of the Cascade Mountains. Completely fenced area at ground level for the doggos, and you can walk them along the canal road on the property. Awesome dedicated Wifi, and a private, completely separate space from the owner.

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, 202 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 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, 362 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

A spacious living area features a king bed with a wooden frame against a backdrop of a cedar ceiling. A dining table and two chairs are positioned alongside a cozy seating arrangement, with large windows allowing natural light to fill the room.

Guesthouse in Bend

4.99 out of 5 average rating, 645 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.

Top guest favorite

A well-appointed bathroom features a white toilet and a pedestal sink with a mirror above. A shower with a clear curtain is in one corner. Wall-mounted planters hold small plants, while neatly arranged towels hang nearby.

Guesthouse in Bend

4.95 out of 5 average rating, 312 reviews

Cabin on quiet 3 acres 10 min to downtown Bend.

Enjoy the peaceful serenity of our guest house. Enjoy a large lawn, irrigation pond with deck for hanging out, and a firepit. Our home is 10 minutes drive to downtown Bend; 45 minutes to Mt Bachelor; 40 minutes to Smith Rock; 20 minutes to Phil's trailhead for mountain biking (All times are without rush hour traffic). Come enjoy all that Bend has to offer!