Guesthouse vacation rentals in Bend

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Popular amenities for Bend guesthouse rentals

Family-friendly guest house rentals

Top guest favorite
A tranquil country road stretches into the distance under a clear blue sky, featuring a vibrant double rainbow arching above. Fenced pastures are visible on either side, with patches of grass and dried earth. The road is wet, reflecting the colors of the rainbow.
Guesthouse in Bend
4.96 out of 5 average rating, 254 reviews

Quiet peacful country living close to everything!

MaryRating, 5 stars1 week ago
What a peaceful space close to town and other locations. I really appreciated the cleanliness and homey feel. Dart board, pool table, and horseshoe pit was a mega plus. Will def stay here again next time I adventure in the Bend area. Thanks Cory for hosting!!
Guest favorite
A cozy living room features a large window allowing natural light and a view of the neighborhood. A fireplace is centered against a textured wall, surrounded by potted plants. Comfortable seating includes a couch with decorative pillows and two armchairs, accompanied by a coffee table placed on a patterned area rug.
Guesthouse in Bend
4.77 out of 5 average rating, 62 reviews

6th Street Slumber - 2 Bedroom Guest House

JamesRating, 5 stars22 months ago
This was my first time in Bend, a few friends and I stayed here for a night while we attended a concert. We didn't get to spend much time here but I highly recommend it. The neighborhood is quiet, peaceful, safe, and close to everything. Check-in was super easy and the house was very clean, nicely appointed, comfortable, etc. I'll definitely stay here again next time I'm in Bend.
Guest favorite
The exterior of a charming cottage features a combination of dark siding and a wood-shingled gable. Large front windows allow natural light to enter, while colorful flower beds and landscaping enhance the inviting entrance. A stone pathway leads to the covered porch area.
Guesthouse in Sisters
4.9 out of 5 average rating, 229 reviews

Sisters Casita Cottage

AmeliaRating, 5 stars1 week ago
Excellent location and restful nights sleep!
Guest favorite
A spacious studio is highlighted by a wooden bed frame, complemented by a cozy leather sofa and a simple coffee table. Natural light enters through multiple windows, illuminating the soft carpeting and intimate setting, suitable for relaxation after outdoor activities.
Guesthouse in Bend
4.94 out of 5 average rating, 217 reviews

Large Craftsman Studio

EllenRating, 5 stars2 weeks ago
great location. private. very comfortable studio.
Top guest favorite
The exterior of a two-story yellow house is displayed, featuring a balcony with railings and an entrance that leads to a deck. A patch of green lawn is visible, bordered by a rustic fence and trees, creating a serene outdoor environment.
Guesthouse in Bend
4.97 out of 5 average rating, 230 reviews

Artist Studio with sleeping Loft

RyanRating, 5 stars6 days ago
Carrie and Dave’s was perfect for a long weekend. The stay was very peaceful and comfortable. I enjoyed Dave’s artwork in the studio - a really nice spot for 1-2 people. Looking forward to staying again in the future!
Top guest favorite
A guest house is visible against a backdrop of trees and a large grassy lawn. A deer stands peacefully in the foreground, while a covered grill and two chairs are positioned near the entrance of the rustic building.
Guesthouse in Bend
4.95 out of 5 average rating, 312 reviews

Cabin on quiet 3 acres 10 min to downtown Bend.

MollyRating, 5 stars2 months ago
We would stay again! Wildlife is easily viewable from the windows. The bed is very comfortable. Serene is a great host!!!
Top guest favorite
A spacious open area features a large wall lined with bookshelves filled with an array of books. A wooden ladder leans against the shelves, providing access to the upper titles. A circular dining table surrounded by four chairs is positioned nearby, with ample natural light coming through the windows.
Guesthouse in Bend
4.95 out of 5 average rating, 750 reviews

Cozy Bookworm's Retreat in Bend

RileyRating, 5 stars3 weeks ago
Amazing space that allows you to get cozy and comfortable. The pieces of home that you always want when you're away. We appreciated the futon and really enjoyed the full kitchen. Thank you for the art and books which make it a place that you want to stay in and explore. Home away from home, it is a magical space that provides everything you need. Spacious and clean!! I wish I brought earplugs because a neighbor dog was barking early from 8-9am. However they mentioned that wasn't usual. Other than that, we were so grateful our stay at Mark and Stephanie's place Thank you! So special and inspiring!

Guest house rentals with a patio

Top guest favorite
A newly renovated kitchen and living area features modern cabinetry and stainless steel appliances. A dining table with four chairs is positioned near a comfortable seating area with a couch. Large windows allow natural light to fill the space, offering views of the surrounding area.
Guesthouse in Bend
5 out of 5 average rating, 61 reviews

Best of NW Bend! Mins to trails, lakes and river!

ErinRating, 5 stars2 months ago
A cute and comfortable apartment for our family of four. The bunk beds in the sleeping nook were awesome for the kids! The location is right on the way to the mountain we were able to be cross country skiing in less than 15 minutes.
Top guest favorite
A well-lit living area features a gray sofa paired with a neutral coffee table resting on a decorative area rug. A stylish floor lamp stands nearby, and a television is mounted on the wall. Large windows allow natural light to brighten the space.
Guesthouse in Bend
5 out of 5 average rating, 40 reviews

Private guest house on 2.5 acres

MaiRating, 5 stars1 week ago
Great, quiet location. made my first time trip to Bend extra special with my puppy. when we arrived the home already had the air on which was nice considering how hot it was when we got out of the car after a long drive from Portland . it's in a rural area outside of the city which is nice because it's quiet and there's not a lot of traffic. there's very little light pollution so looking at the stars at night from the house was absolutely beautiful. also whatever bone toy they had in the house for the visiting dogs, my puppy went absolutely crazy for. I had to look it up on Amazon and buy one for myself because she would not stop chewing it!! only thing I'd note is that we saw fire ants in the driveway but it was easy to just step over quickly. we just made sure to carefully carry our puppy over them so that she wouldn't get bitten. overall if I'm staying in bend again I'd stay here again.
Top guest favorite
A cozy sleeping area features a queen size bed adorned with a colorful patterned cover. Bright yellow walls are accented by a creative sun mural and wood paneling. Reading lights are mounted on either side of the bed, while a comfortable orange armchair adds a pop of color.
Guesthouse in Bend
5 out of 5 average rating, 52 reviews

The Sunshine Loft

SophieRating, 5 stars2 days ago
Katie and Brooks were absolutely lovely hosts. With their friendly greeting upon arrival, long list of local recommendations, and stunning property with the most amazing view, we felt SO comfortable during our stay. By far the best Airbnb we have stayed in!!
Top guest favorite
A comfortable living area features a wooden sofa adorned with patterned cushions, complemented by a wooden coffee table. Lush plants are positioned nearby, and large windows allow natural light to fill the space, offering views of the surrounding greenery.
Guesthouse in Bend
5 out of 5 average rating, 24 reviews

High Desert Escape

CarolineRating, 5 stars1 week ago
We loved staying at Stephen and Russia’s place! The unit felt huge, I loved the space. Everything was spotless, each room was perfect and had everything we could need. When we had questions they answered immediately. So happy we chose this place while visiting Bend.
Guest favorite
A cozy indoor space features a spacious bed with a unique wooden headboard. A small kitchenette area is visible in the background, equipped with a microwave. A ceiling fan provides airflow, while a bathroom can be glimpsed through an adjoining door.
Guesthouse in Redmond
4.93 out of 5 average rating, 29 reviews

Marla’s Cozy Shop ADU

GaryRating, 5 stars2 weeks ago
My girlfriend, dog, and I wanted to spend Memorial Day weekend in the Redmond/Bend area and Brady's AUD provided the perfect space for us to rest and relax between all the outdoor activities! Also loved how they offered parking permits for attractions like Smith Rock. Would definitely stay again!
Top guest favorite
A modern kitchen is visible, featuring sleek cabinetry and a large round wooden table surrounded by four chairs. Natural light filters in through windows, illuminating the space. The kitchen is equipped with stainless steel appliances, and a small plant adds a touch of greenery.
Guesthouse in Redmond
5 out of 5 average rating, 26 reviews

Newly built, high desert sunsets & mountain peaks

CameronRating, 5 stars1 week ago
Beautiful loft. Amazing and responsive host. Super clean and a very well stocked kitchen. Beds were AMAZING!!! Thank you so much Tiffany you have such a beautiful place!
Top guest favorite
A bright living area showcases a dark leather sofa, a vibrant red armchair, and a round coffee table with a woven design. Large windows offer views of surrounding trees, while light wood flooring provides a warm contrast. Chic decor elements, including a TV and a dining table, enhance the space.
Guesthouse in Bend
5 out of 5 average rating, 12 reviews

Treetop Retreat on West Side. Walk to town.

LaurenRating, 5 stars2 months ago
I had the most incredible stay at the Treetop Retreat in Bend. Steve and Lynn have created a truly special space—this custom-built unit is even more stunning in person than the photos show. Everything is brand new, beautifully designed, and stocked with everything you could possibly need for a long-term stay. They went above and beyond to make me feel welcome, inviting me to dinners, sharing drinks, and even letting me borrow snowshoes for local adventures. Their recommendations for things to do and places to explore around Bend were spot on, and the location in River West is absolutely ideal. I absolutely loved my time here and will definitely be back. Highly, highly recommend.
Guest favorite
Double doors open to a spacious private patio furnished with bright blue chairs, offering views of a serene outdoor area surrounded by trees. A small table is positioned nearby, providing a comfortable setting for relaxation in nature.
Guesthouse in Bend
5 out of 5 average rating, 7 reviews

Modern East Side 1-Bedroom Suite with a View

AngelaRating, 5 stars10 months ago
Long story short. If you would like to stay somewhere peaceful, this is the place. If you want to get away from the tourists and stay on a secure property, surrounded by nature, and amazing animals, you need to book this place! It was so quiet and beautiful! Chad is the nicest guy I met in Oregon. Honestly, it was a blessing his place was available for my husband and I to stay. Thank you, Chad! We hope to see you again.

Guest house rentals with a washer and dryer

Guest favorite
A modern hot tub is situated in a shared courtyard area, featuring jets and bubbling water. The hot tub is surrounded by a concrete surface and wooden steps leading to the entrance of the studio. The area is designed for relaxation and social use.
Guesthouse in Bend
4.92 out of 5 average rating, 13 reviews

NWBend Urban Studio super location with hot tub!

SamRating, 5 stars1 week ago
Christie's place feels new and very pristine. The location is really good - literally across the street from my favorite market in Bend as well as a coffee shop which was even closer. The neighborhood was quiet and safe. I stayed for a month and used the apartment as a base for finding real estate in the Bend area. A special treat for me ending each day in the hot tube which is very private and kept sparkling clean. Christie's place was a great place for me to be for an extended stay in Bend.
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, 251 reviews

Modern Downtown Cottage near Outdoor Adventure

CatieRating, 5 stars2 weeks ago
Nice space, kitchen is well stocked and I love the big island. I appreciated the dark window shades and found the space very quiet which was perfect for me as I was in town for work. Plenty of parking space. I would stay again when back in town!
Guest favorite
An aerial view of the Brasada Ranch resort showcases a modern building nestled among natural landscapes. Two swimming pools, one featuring a water slide, are surrounded by lounge chairs. Rolling hills and other resort buildings are visible in the background under a partly cloudy sky.
Guesthouse in Powell Butte
4.83 out of 5 average rating, 18 reviews

Aspen Willow Casita | Brasada Ranch | Sleeps 4

JamieRating, 5 stars2 months ago
Immaculately clean, newer construction. The planned community this property is located within is really, really pretty. Gorgeous landscaping, mountain views. This house is right off a walking trail, which was lovely. It’s out in the country a bit, so there were loads of stars at night and the sound of frogs in a nearby pond. We wanted to be located close enough for day trips to both the Painted Hills and Bend, and that worked out great for us. Highly recommend.
Top guest favorite
The exterior of The Nest is displayed, featuring a wooden sign with the name prominently displayed. A warm light fixture above illuminates the sign. Below, small plants are arranged neatly in a wooden planter box against the metallic wall.
Guesthouse in Redmond
4.94 out of 5 average rating, 72 reviews

Unique & quiet w/Hot tub!

MeghanRating, 5 stars1 week ago
This place was really cool. Very quiet, intimate, clean, and had all amazing amenities! Would love to stay here again!
Superhost
The kitchen area features modern cabinetry and a compact dining table with two high-backed stools. A television mounted on the wall displays nature imagery. Stainless steel appliances, including a microwave and coffeemaker, are neatly arranged, while natural light highlights the wood flooring.
Guesthouse in Bend
4.86 out of 5 average rating, 115 reviews

WHOLE HOUSE! Tiny Home on Bend's East Side

JesseRating, 5 stars2 months ago
The minni house had everything we needed and was a great spot for us to call home while we explored central Oregon
Superhost
A charming exterior view of the Canal Cottage is presented, featuring a covered porch with a fireplace and seating area. Surrounding pine trees and well-maintained grass enhance the tranquil setting, while large windows provide a glimpse of the cozy interior.
Guesthouse in Bend
4.75 out of 5 average rating, 20 reviews

Canal Cottage, 20 Min to Bachelor, Dog friendly

RobRating, 5 stars1 week ago
Such a great place to relax near Bend, Mt Bachelor and so many other hiking areas. Our dog loved running around the large yard. The inside is perfect and cozy place to setting in after a day outside and the grill was great to cook on. Make sure you bring bug spray! The mosquitos can be intense out that way.
Guest favorite
A panoramic view of open land surrounded by a wooden fence, featuring green grass in the foreground. Trees and shrubs are visible in the background under a cloudy sky, creating a serene outdoor setting.
Guesthouse in Terrebonne
4.9 out of 5 average rating, 275 reviews

Compound Coziness...Terrebonne Guesthouse

AliciaRating, 5 stars1 month ago
The pictures don’t really do this place justice. It’s actually quite spacious and we ended up sleeping on the lower bunk bc it’s so low to the ground which was great for our dachshund. It was SO comfortable. Nicole was extremely responsive which was great since we checked in pretty late and had a few questions. I will definitely stay again, the fenced in areas are actually fenced in so our 12 pound furbaby couldn’t escape easily. Great location super close to everything although just outside enough you felt in the country. It is off the highway, but it’s tucked far enough off the road that we couldn’t hear the highway really. Great place!! We even watched an old VCR tape and it was nostalgic :)
Guest favorite
Guesthouse in Bend
4.96 out of 5 average rating, 83 reviews

Dog Friendly~Central Location~Modern Construction

JohnRating, 5 stars9 months ago
We had a great stay at Daniel's place--it was extremely clean, the beds were very comfortable and he was quickly responsive when I communicated with him. We are already looking forward to our next stay in Bend and I will try and book this place again or Daniel's other unit!

Quick stats about guesthouse rentals in Bend

  • Total rentals

    80 properties

  • Nightly prices starting at

    ﺩ.ﺇ184 before taxes and fees

  • Total number of reviews

    10K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

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