Guesthouse holiday rentals in Bend

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Top-rated Guesthouses in Bend

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Guest favourite

Guesthouse in Bend

4.96 out of 5 average rating, 730 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.

Superhost

Guesthouse in Bend

4.91 out of 5 average rating, 683 reviews

Artisanal Tiled Custom Built w/Hot tub & Livestock

Our artistic studio is located on a small family farm with a country feel yet close to everything Bend has to offer. Outside we have a pig, chickens, large fenced yard, hot tub, beautiful views. Inside you'll find tons of tile mosaics, stainless steel appliances, hand built European cabinets, Heated floors, custom walk in shower, lots of plants and original artwork. You will have a private studio with no shared spaces that includes a queen bed, kitchen, living room, bathroom, lawn and hot tub.

Guest favourite

Guesthouse in Bend

4.97 out of 5 average rating, 223 reviews

Midtown gem I Park view I Full kitchen I Fireplace

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!

Guest favourite

Guesthouse in Bend

4.99 out of 5 average rating, 102 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 favourite

Guesthouse in Bend

4.98 out of 5 average rating, 397 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.

Guest favourite

Guesthouse in Bend

4.93 out of 5 average rating, 164 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!

Guest favourite

Guesthouse in Bend

5 out of 5 average rating, 237 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.

Guest favourite

Guesthouse in Bend

4.93 out of 5 average rating, 316 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.

Superhost

Guesthouse in Bend

4.86 out of 5 average rating, 111 reviews

WHOLE HOUSE! Tiny Home on Bend's East Side

Welcome home to this tiny house, The Minni House! Located on the east side of Bend on the back of a beautiful treed lot across from a city park, this Minni retreat is the perfect place to experience tiny house living while visiting Bend. It is new construction, designed in comfortable contemporary colors and styles with everything you need and nothing you don't. Simple living, beautifully done. It has everything you need, and nothing you don't!

Guest favourite

Guesthouse in Old Bend

4.95 out of 5 average rating, 146 reviews

The Arrow Cottage—a historic Bend mill cottage

The Arrow cottage is located in the heart of Bend between the historic downtown and desirable Old Mill district. It is truly the perfect location, just steps from the Columbia river park, walking distance from the amphitheater, 10 Barrel Brewery, Good Life Brewery, Jackson's Corner and Active Culture to name a few. Our complimentary bikes make make it easy for you to zip downtown for your morning coffee or evening happy hour.

Guest favourite

Guesthouse in Bend

4.95 out of 5 average rating, 302 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!

Superhost

Guesthouse in Bend

4.88 out of 5 average rating, 216 reviews

TheTiny Ranch House

This is a great little place with a great price. Stay in our comfortable and extremely clean, private entranced tiny home. This hip little town has emerged as an international destination for endless, year round outdoor recreation, a bustling micro-brewery culture and a diverse food & restaurant scene. We’ll keep you comfortable so you can get out there!