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 bright and spacious studio apartment features large windows allowing natural light to fill the room. Comfortable seating is complemented by a dining area and modern kitchenette, while polished hardwood floors enhance the open layout. A ceiling fan provides additional air circulation.

Guesthouse in Bend

4.96 out of 5 average rating, 771 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

A spacious living room is featured with a gas fireplace and a large-screen TV, complemented by a pull-out sofa. Large windows allow natural light to fill the room, while bar seating is available at the open kitchen, creating an inviting atmosphere for relaxation or gatherings.

Guesthouse in Bend

4.97 out of 5 average rating, 273 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!

Guest favorite

An open living space is visible, featuring a comfortable black couch with a plaid throw. A modern kitchen area with stainless steel appliances is seen, along with a dining table in the background. Warm wood flooring enhances the inviting ambiance.

Guesthouse in Terrebonne

4.86 out of 5 average rating, 259 reviews

Near SmithRock pets ok low cost private cold ac

close to smith rock. golf course, tennis court, store, 3 bars, 5 minutes away. ample parking. We live on 4 dusty acres, and are pet friendly, so although we pride ourselves on the cleaning and sanitizing we perform between guests we also ask if you are super picky please refrain from booking, this is definitely not a luxury hotel in the city. If there are any discrepancies upon arrival please let us know.. We try to keep our price the lowest in the area, and strive to attain that 5 star review.

Top guest favorite

A cozy sleeping area features a queen size bed dressed in neutral tones, complemented by decorative pillows. Natural light filters through a window covered with wooden blinds. A small wooden table and stool are situated nearby, providing additional functional space.

Guesthouse in Bend

4.99 out of 5 average rating, 129 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!

Superhost

Three ukuleles are displayed on wall-mounted hooks against a light-colored wall. The instruments feature varying wood grains and colors, showcasing their unique designs. Each ukulele is identified with a tag hanging from the neck, adding to the artistic arrangement.

Guesthouse in Bend

4.92 out of 5 average rating, 112 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

The bedroom features a spacious bed with white linens, complemented by two bedside tables with lamps. A green bench sits at the foot of the bed, while a landscape painting hangs above the headboard. Soft curtains frame a window, allowing natural light to fill the space.

Guesthouse in Bend

4.98 out of 5 average rating, 129 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

A spacious living area features two comfortable sofas adorned with colorful decorative pillows. A coffee table sits in the center, and a large bed is positioned in the background, draped in a bright quilt. Natural light floods through large windows, illuminating the open space.

Guesthouse in Bend

4.98 out of 5 average rating, 415 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, 173 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 comfortable living area features a spacious sofa and two armchairs, with a wooden dining table visible. Large windows allow natural light to fill the space, showcasing views of greenery. A television is mounted on the wall, and a colorful artwork adds a touch of style.

Guesthouse in Bend

4.93 out of 5 average rating, 381 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 modern living space features a light-filled open layout, showcasing a comfortable gray sofa with coordinating pillows. A stylish wooden coffee table complements the area. The kitchen, equipped with sleek cabinetry and appliances, is visible in the background, promoting a functional and inviting atmosphere.

Guesthouse in Redmond

4.98 out of 5 average rating, 266 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.

Guest favorite

A spacious bed is adorned with various blue and plaid decorative pillows. A wall-mounted television is visible, along with a black storage cabinet. Natural light enters through a small window, framed by light curtains. A rustic wall decoration adds character to the space.

Guesthouse in Old Bend

4.96 out of 5 average rating, 166 reviews

Charming studio in the heart of town

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.

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, 661 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.