Guesthouse holiday rentals in Deschutes County

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Deschutes County guesthouses

Family-Friendly guesthouses

Top Guest favourite
Guesthouse in Bend
4.96 out of 5 average rating, 254 reviews

Quiet peacful country living close to everything!

MaryRating, 5 stars3 weeks 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!!
Superhost
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 favourite
Guesthouse in Sisters
4.9 out of 5 average rating, 230 reviews

Sisters Casita Cottage

VictoriaRating, 5 stars1 week ago
Comfortable cute space. Walking distance to all downtown stuff.
Guest favourite
Guesthouse in Bend
4.85 out of 5 average rating, 527 reviews

Cozy & Convenient Downtown Cottage

MarieRating, 5 stars1 week ago
The guest home was located very close to downtown Bend , grocery stores and the river walk, walkable , with no need for a car. The kitchen had all we needed with plenty of coffee, tea, and cooking supplies. Paula was very responsive, kind and flexible . I would highly recommended staying here.
Guest favourite
Guesthouse in Bend
4.94 out of 5 average rating, 217 reviews

Large Craftsman Studio

EllenRating, 5 stars1 month ago
great location. private. very comfortable studio.
Guesthouse in Redmond
4.9 out of 5 average rating, 71 reviews

The Little Rojo House - with private entrance.

JoeRating, 5 stars58 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
Top Guest favourite
Guesthouse in Bend
4.95 out of 5 average rating, 752 reviews

Cozy Bookworm's Retreat in Bend

ShelbyRating, 5 stars1 week ago
Peaceful, cozy, artistic!! We had a lot of outdoor activities planned for our short stay but found ourselves wanting to stay at the little house to read and watch movies :) it is very inviting and walking/biking distance to many good restaurants and the beautiful river. Everything was clean and hosts were kind, hospitable, and great communicators. We’d love to go back.

Guesthouses with a patio

Top Guest favourite
Guesthouse in Bend
5 out of 5 average rating, 62 reviews

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

BronwynRating, 5 stars3 weeks ago
Exactly what we wanted. We had an extended stay in this rental and felt right at home. Small space lives large, with tons of light and an incredible view. Appreciated the private yard and bike storage. And the location? Amazing! 3-4 mile commute to Phils trail head made for easy and frequent biking. We walked to Old Mill, downtown and Galveston area frequently. 2-3 mile walk each way so it’s not for the faint of heart, but it’s a great way to burn off the food and beer 🙃 and the hosts were fantastic. Easy to reach and always quick to help people if something came up. 10/10!
Top Guest favourite
Guesthouse in Bend
5 out of 5 average rating, 43 reviews

Private guest house on 2.5 acres

SarahRating, 5 stars1 week ago
The place was just as described, and perfect for our family for the week!
Superhost
Guesthouse in Sisters
4.7 out of 5 average rating, 237 reviews

Downtown Sisters Suite - Hot Tub - Dog Friendly

JennaRating, 5 stars1 week ago
The location was great, just a few blocks off the main area but far enough away we had peace and quiet from the hubbub. The beautifully green fenced yard was an actual godsend and a true game changer. That alone makes this Airbnb worth it if you’re traveling with your dog. The Adirondack chairs were nice to have. The hot tub was nice and the view of the mountains from it so luxe! The actual unit was a tiny bit smaller than I expected but still a great size for my parents and I, and otherwise just as pictured. Another reviewer said they didn’t like the bed but my parents said it was fine. I laid on it and it seemed big and comfy. I didn’t try the pullout couch bed because I find them to be hard on my back so I brought a floor mattress with me. The second night we could hear some noise from the adjoining unit but the host responded right away and handled it. The temp is set at 69 which was fine for me but my mom was a little chilly. I would definitely stay here again. Great host!
Guest favourite
Guesthouse in Terrebonne
4.97 out of 5 average rating, 30 reviews

Rusty Ranch Inn

DarrenRating, 5 stars4 weeks ago
Great place. We've stayed here twice now and it was good to us both times.
Top Guest favourite
Guesthouse in Bend
5 out of 5 average rating, 26 reviews

High Desert Escape

TracyRating, 5 stars1 week ago
We loved our stay at this gorgeous home in Bend. The hosts were flexible with check-in time and were very responsive with communication. This is hands down one of the best AirBnbs I have ever stayed at and can’t wait to return for a future visit! The decor was beautiful, bed comfortable and this home had so many little extra touches. Truly a wonderful experience! Thank you for hosting us.
Guest favourite
Guesthouse in Redmond
4.94 out of 5 average rating, 33 reviews

Marla’s Cozy Shop ADU

TroyRating, 5 stars1 week ago
It is a great place to stay, very small and cozy. And the cat is as friendly as can be!
Top Guest favourite
Guesthouse in Redmond
5 out of 5 average rating, 27 reviews

Newly built, high desert sunsets & mountain peaks

ShathabishRating, 5 stars1 day ago
Great place for a stay in Redmond. As other guests have alluded to, this home stands out for overall cleanliness, the beds are very comfortable and the clean dishes in the kitchen are a definite plus. Tiffany is a really good host and very responsive. She left farm fresh eggs and welcome beverages for us and also asked what my toddler likes for toys and provided some Legos and magna tiles, which my toddler went straight to. Highly recommended!
Guest favourite
Guesthouse in Bend
4.77 out of 5 average rating, 13 reviews

Charming 1-Bedroom Guest House on Hobby Farm

RachelRating, 5 stars10 months ago
We loved our stay! We were grateful to find a local option for a midweek stay while renovation work at our own house was underway. We were all comfortable (including our dog) and were able to work from the space during the day, and walk the property, visit with the goats/chickens, and take in the beautiful scenery anytime. Chad was a wonderful and thoughtful host who went above and beyond. We had everything we needed.

Guest house rentals with a washing machine and dryer

Guest favourite
Guesthouse in Prineville
5 out of 5 average rating, 10 reviews

Discovery Loop Landing

SavanahRating, 5 stars9 months ago
Amazing house. Clean and well stocked. Host was great to communicate with. Home away from home for our first guys. Will absolutely stay again.
Guest favourite
Guesthouse in Bend
4.88 out of 5 average rating, 112 reviews

McKinley Place - A Retreat in SE Bend

ArielRating, 5 stars3 weeks ago
One of our favorite places we have stayed in! It was beautiful, comfortable, and had everything we needed.
Superhost
Guesthouse in Bend
4.86 out of 5 average rating, 116 reviews

WHOLE HOUSE! Tiny Home on Bend's East Side

JesseRating, 5 stars3 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
Guesthouse in Bend
4.75 out of 5 average rating, 20 reviews

Canal Cottage, 20 Min to Bachelor, Dog friendly

RobRating, 5 stars3 weeks 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 favourite
Guesthouse in Terrebonne
4.9 out of 5 average rating, 277 reviews

Compound Coziness...Terrebonne Guesthouse

TedRating, 5 stars3 weeks ago
We were in town for baseball. Location was great for accessing the various fields. Everyone slept well. We stayed in late May with temperatures in the high 70's during the day. The house stayed comfortably cool with the windows open. Cows were cute.
Guest favourite
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!
Guest favourite
Guesthouse in Bend
4.95 out of 5 average rating, 105 reviews

Century Chalet - Tons of Light & Amazing Location!

HeatherRating, 5 stars2 weeks ago
This spot was amazing! My friend and I were in Bend for a long weekend to see Leon Bridges at the Hayden Amphitheatre and this spot was absolute perfection. The space is beautiful, so much natural light pours through the whole house, and it was impeccably clean. I would highly recommend this spot and would absolutely stay again!
Top Guest favourite
Guesthouse in Bend
4.98 out of 5 average rating, 409 reviews

Bend Ranch Guesthouse on 20 acres

KariRating, 5 stars3 weeks ago
Fantastic experience and my family really enjoyed the dogs (Hi Willow!), goats and chickens. Orion was friendly and welcoming, giving us fresh chicken eggs. Had a lovely walk around the property at sunset with views of the mountains. Wish we had more time to spend there!! Will be back!!

Destinations to explore