Guesthouse vacation rentals in Bend

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Top-rated guesthouse rentals in Bend

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Top guest favorite

A modern kitchen area features sleek dark cabinetry and a light-colored marble countertop. An integrated stove and a stainless steel dishwasher are included. Above, a round wall shelf displays various glassware and decorative items, enhancing the functional space.

Guesthouse in Bend

4.96 out of 5 average rating, 748 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 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, 108 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

Aerial view of a river winding through a vibrant town. Lush greenery borders the water, with shops and buildings visible along the shore. In the background, distant hills create a serene backdrop, while the warm light of sunset enhances the scene.

Guesthouse in Bend

4.99 out of 5 average rating, 103 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 tranquil view of a pond surrounded by tall grasses and trees. In the background, a spacious guesthouse is visible next to a variety of evergreen and deciduous trees. The area offers a peaceful, natural landscape that invites relaxation.

Guesthouse in Bend

4.98 out of 5 average rating, 407 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 favorite

A winter landscape showcases a forest of tall snow-covered pine trees under a bright blue sky. The scene is tranquil, with snow blanketing the ground and distant mountains visible in the background.

Guesthouse in Bend

4.96 out of 5 average rating, 374 reviews

BlueSpruce Guesthouse-Walkable RiverTrail/Downtown

The Blue Spruce is a charming, private second story guest house . It is accessed by exterior stairs, private entrance, and self check in. It is cozy, equipped with a full kitchen, sunny living room, 1 BD, and 1 Bath. Convenient location in a quiet neighborhood by downtown Bend, less than a mile to the river trail, coffee shops, brew pubs, and grocery. Great launching pad for mountain biking, hiking, skiing, golfing, fishing, whitewater and countless other adventures, you get the picture!

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, 155 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.

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, 252 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 favorite

A vibrant sunset casts warm tones across the sky, with dramatic clouds set against the silhouette of a snow-capped mountain in the background. Tall trees frame the scene, enhancing the serene landscape.

Guesthouse in Terrebonne

4.9 out of 5 average rating, 272 reviews

Compound Coziness...Terrebonne Guesthouse

Come and join us in gorgeous Central Oregon! The guesthouse is part of our 5 acre property that we live on with our two friendly dogs. Your house has a private fenced in area, but you are welcome to explore the entire property and watch gorgeous sunsets of the Cascade Range. This house provides a queen bed in one room, and a double and twin bunk bed in the second room. A full kitchen and washer/dryer gives you the convience to make this your home during your visit.

Top guest favorite

A private deck extends towards a hot tub, surrounded by tall trees and natural landscaping. Sunlight streams through the branches, illuminating the tranquil outdoor space. A distant view of a barn is seen, enhancing the sense of rural serenity.

Guesthouse in Bend

4.98 out of 5 average rating, 327 reviews

Ranch Cottage: Desert, Forest, Horses, Hot Tub

Beautiful guest cottage studio, with mountain views, in the southeast Bend neighborhood of Sundance. 15 minutes to town and 45 minutes to Mt. Bachelor ski area. This special ranch property is two blocks away from endless recreation in the Deschutes National Forest. Come hike, bike, ride, explore caves, ski, snowshoe, and more right from the door of your private cottage. Includes one king Sleep Number bed and one queen Murphy bed. Private hot tub out the back door.

Guest favorite

A sunroom features large windows allowing abundant natural light. Two white chairs are positioned around a small wooden table, creating a cozy nook for relaxation. The warm wood paneling adds a natural element to the space, and views of the surrounding trees are visible through the windows.

Guesthouse in Bend

4.95 out of 5 average rating, 103 reviews

Century Chalet - Tons of Light & Amazing Location!

We have a beautiful guest house with tons of natural light and all the amenities you'll need in the best location Bend has to offer. 1 Bedroom, 1 Bath, with a sunroom which can easily be used as a second bedroom whenever needed. The house has a full kitchen with stainless appliances. Best of all, you can't get any closer to Mt. Bachelor, the Deschutes, or Bend's trails. All while still being 8 minutes from downtown Bend.

Top guest favorite

A serene deck features a small decorative table and a woven chair, surrounded by lush greenery. Views of the river are visible beyond the railing, complemented by distant trees and a bright sky.

Guesthouse in Sunriver

4.98 out of 5 average rating, 565 reviews

Riverfront on Deschutes River

Located ON the Deschutes River Quiet and private above garage apartment with deck. **23 miles to Mt Bachelor** 5 miles to Sunriver Resort, attend events-GET AWAY FROM THE CROWDS! Easy 20 mile drive to Bend, close to Cascade Lakes area and Three Sisters Wilderness for great hiking. EV charger ChargePoint 40 amp One block to Deschutes Nat’l forest and a trail along the river.

Superhost

The exterior of Kingston Kottage features a rustic facade with vertical wood siding and decorative skis mounted above the door. Ivy climbs the side of the building, and a potted plant is positioned beside the entrance. A wooden fence and gate are visible in the background.

Guesthouse in Bend

4.91 out of 5 average rating, 173 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.