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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, 251 reviews

Quiet peacful country living close to everything!

RickRating, 5 stars2 months ago
We had a great stay at Cory's place in Bend. Very convenient location for our activities. Cory was very responsive to any questions we had. Nice private and quiet location. Would definitely go back.
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, 226 reviews

Sisters Casita Cottage

DianeRating, 5 stars6 months ago
I have stayed here more than once and really appreciate the space. Love the beautiful yard you can sit out front and enjoy her flowers and well kept yard. It’s quiet no road noise!!
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, 225 reviews

Artist Studio with sleeping Loft

SurejRating, 5 stars4 weeks ago
Carrie and Dave were wonderful hosts. Very communiative and friendly. We really enjoyed staying at their beautiful place. We enjoyed the all the artwork and the cozy surroundings.
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
4.93 out of 5 average rating, 215 reviews

Large Craftsman Studio

DaniRating, 5 stars7 months ago
This place was safe and secure and very cozy. Becky was super responsive and nice and the neighborhood was beautiful. I would stay here again :)
Top guest favorite
A cozy living area is presented with a leather couch and a small dinette set. A wooden staircase leads to the loft above, with decorative wall art enhancing the ambiance. The kitchenette is visible in the background, along with modern appliances including a refrigerator.
Guesthouse in Bend
4.97 out of 5 average rating, 66 reviews

Brand new, modern 1 bdrm + loft with open land!

GraceRating, 5 stars8 months ago
I loved staying at this place! Sooo peaceful, you walk outside and it’s quiet just sounds of birds. It was very comfortable to stay at and clean. I also I appreciated the good shower products they had for us so I was able to have good hair days! It is a guesthouse on there property but it was secluded and private and felt like we were all alone. They also provided some little snacks which was nice to have when we went hiking. Great place highly recommend for a peaceful getaway in a beautiful area.
Top guest favorite
A cozy living area is highlighted by a comfortable gray sofa adorned with yellow throw pillows. A round mirror complements the decor, and artwork adorns the walls. Natural light floods in through the large window, creating a welcoming space for relaxation or work.
Guesthouse in Bend
5 out of 5 average rating, 55 reviews

Prime Location for Adventure and Relaxation

RecilleRating, 5 stars3 weeks ago
Phenomenal location!!! We had a great time at Linda’s place. Definitely recommend to everyone who wants to come and visit Bend.
A private deck is framed by wooden trellises, offering views of lush trees and the landscape beyond. Two chairs surround a small round table, all set against a backdrop of natural greenery and open sky, creating a serene outdoor space.
Guesthouse in Redmond
4.9 out of 5 average rating, 71 reviews

The Little Rojo House - with private entrance.

JoeRating, 5 stars56 months ago
Great space for an extended stay in Redmond with easy access to Bend and many outdoor activities. Loved that it had a full kitchen since I like to cook a lot

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 stars3 weeks 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, 29 reviews

Private guest house on 2.5 acres

MarcyRating, 5 stars1 week ago
We absolutely loved the rural country location and were able to take lots of walks with the dog and bike rides straight from the house. Definitely a quiet and peaceful oasis. The little house met our needs perfectly and was adorable in all ways. We will definitely stay there again if it’s available.
Superhost
A spacious hot tub is positioned on a concrete pad, surrounded by a privacy fence with warm outdoor lighting. A fire pit and comfortable seating area are nearby, creating an inviting outdoor setting. The exterior of the modern guest suite is visible in the background, framed by a colorful sunset.
Guesthouse in Sisters
4.71 out of 5 average rating, 229 reviews

Downtown Sisters Suite - Hot Tub - Dog Friendly

YiannaRating, 5 stars4 weeks ago
The space was as advertised. The fenced backyard is great for pet, good location, and the hot tub is a nice addition. The hosts have great communication.
Guest favorite
The main sleeping area features two queen beds with green upholstered headboards, complemented by nightstands with table lamps. Natural light filters in through a window adorned with light curtains. A textured area beneath the beds enhances the design, providing a cozy and comfortable space.
Guesthouse in Sisters
4.83 out of 5 average rating, 6 reviews

Charming Sisters Cottage

LaurenRating, 5 stars3 months ago
We had a great time staying at Mary’s place in Sisters. Thanks for the clean and comfortable spot in a great location!
Guest favorite
The exterior of Rusty Ranch Inn is shown with a modern design featuring a combination of wood and metal siding. A large window provides views of the interior, while a wooden fence lines the property. Gravel parking is available in front.
Guesthouse in Terrebonne
5 out of 5 average rating, 27 reviews

Rusty Ranch Inn

DavidRating, 5 stars7 months ago
I thought it was very nice. They had everything we needed to prepare meals and I loved the covered patio and backyard. I hope to get there 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, 40 reviews

The Sunshine Loft

AllisonRating, 5 stars2 months ago
Katie and Brooks were both very friendly and welcoming to us during our stay ! Would highly recommend them as hosts to anyone looking for a place to stay near Bend. :)
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, 19 reviews

High Desert Escape

JulianRating, 5 stars3 weeks ago
This place is truly special. The second-floor concept is quite unique in Bend, and it really creates a sense of serenity and peace, like you're in your own little tree house nest. We could have stayed there the whole time – it's so cozy and calm. The daybed in the living room next to the big main window is the place to be! And Stephen and Rissa were excellent hosts, answering questions promptly and helping us out with some logistics. This will be our go-to-place whenever we come to Bend. Top recommendation!
Top guest favorite
Guesthouse in Redmond
4.94 out of 5 average rating, 68 reviews

Unique & quiet w/Hot tub! No check Out list!

LukiaRating, 5 stars1 month ago
Janey was responsive and had clear instructions for everything first hand and very thoughtful. If we had a question she was quick to respond and communicated well, the place was awesome it was the perfect little place to stay that’s more private and quiet. We were in love with this place and would definitely come back!

Guest house rentals with a washer and dryer

Superhost
A bright studio features a queen bed adorned with decorative pillows and a textured blanket. A stylish kitchenette with modern cabinetry is visible, alongside a floral accent wall and ample natural light from the nearby window. A cozy seating area is also included.
Guesthouse in Bend
4.33 out of 5 average rating, 3 reviews

Millpointe Studio 1.0, Where Luxury Meets Location

KristyRating, 5 stars1 week ago
Wonderful place and perfect location! Beautiful and warm and welcoming!
Guest favorite
Guesthouse in Bend
4.93 out of 5 average rating, 354 reviews

Suburban Forest guest house with garage

KeithRating, 5 stars3 weeks ago
instructions for check in and check out were very clear and easy to follow. Great location and lots to do and see in Bend. Very enjoyable couple days at this airbnb.
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, 243 reviews

Modern Downtown Cottage near Outdoor Adventure

ThavishaRating, 5 stars4 weeks ago
Great place to stay! Would highly recommend.
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, 252 reviews

Midtown gem I Cozy Fire I Full kitchen I Park View

VanessaRating, 5 stars2 weeks ago
Aaron and Emily’s place was very clean and quiet for our visit to Bend. Very responsive and very dog friendly. Great park across the street. Quiet neighborhood and a quick drive to most everything! Would stay again!
Superhost
The open-concept living area features a modern kitchen with sleek cabinetry and an island with seating for two. A dining table for four is positioned beside a window, while a comfortable seating area includes a green couch and contemporary decor on a side table.
Guesthouse in Bend
4.87 out of 5 average rating, 108 reviews

McKinley Place - A Retreat in SE Bend

JillynRating, 5 stars1 month ago
Excellent haven for two besties on a long weekend! Unit is easy to find and well-maintained - was spotless upon arrival. At time of writing (2025), has new modern plumbing fixtures and appliances. En suite bathrooms for the two bedrooms were the selling point, yet we ended up loving even more features. We were each able to have necessary phone calls in our rooms without disturbing the other's sleep. Kitchen is thoughtfully equipped with impressive variety of items - much more than listed. We enjoyed a self-curated yarn & book crawl, hit a couple local restaurants, and otherwise mostly cooked for ourselves and enjoyed the cozy quiet with the tea kettle always on. Barely communicated with host because our needs were met at every turn. Highly recommend!
Top guest favorite
Guesthouse in Redmond
5 out of 5 average rating, 23 reviews

Newly built, high desert sunsets & mountain peaks

RobynRating, 5 stars4 months ago
The place had everything we needed and then some! Tiffany was so thoughtful, from the welcome note/drinks, to setting up the coffee pot for our first morning, she made it a wonderful home away from home! We would 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 stars1 month ago
The minni house had everything we needed and was a great spot for us to call home while we explored central Oregon
Top guest favorite
The exterior of a modern, wooden guesthouse is showcased, featuring a spacious balcony with wooden railings. A set of stairs leads to the upper entrance. Below, a large garage door is visible, along with two bicycles parked neatly against the wall.
Guesthouse in Bend
5 out of 5 average rating, 33 reviews

Ponderosa Cabin — Modern Home & Amazing Location!

KristenRating, 5 stars3 months ago
We had a great stay at Marks apartment. The place is beautiful and cozy and perfect for a quiet week in Bend. The location is walking distance from everything you could want; restaurants, grocery store, etc. We especially loved that it is dog friendly and our pup got to play with their two sweet dogs. Would highly recommend this stay!

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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