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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Bend guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Sisters
4.9 out of 5 average rating, 208 reviewsSisters Casita Cottage
Aug 26 – Sep 2
Guesthouse in Bend
4.98 out of 5 average rating, 252 reviewsCountry Apartment, Tumalo 2BR
May 28 – Jun 4
Guesthouse in Bend
4.95 out of 5 average rating, 676 reviewsCozy Bookworm's Retreat in Bend
Jan 9 – 16
Guesthouse in Bend
4.94 out of 5 average rating, 207 reviewsLarge Craftsman Studio
Oct 7 – 14
Guesthouse in Bend
4.8 out of 5 average rating, 274 reviewsThe Bivouac of Bend
Jun 6 – 13
Guesthouse in Bend
4.85 out of 5 average rating, 485 reviewsCozy & Convenient Downtown Cottage
Dec 1 – 8
Guesthouse in Bend
4.96 out of 5 average rating, 55 reviewsBrand new, modern 1 bdrm + loft with open land!
Jun 3 – 10
Guest house rentals with a patio
Guesthouse in La Pine
4.94 out of 5 average rating, 108 reviewsPonderosa Pines Bunkhouse - Dog friendly ADU
Mar 3 – 10
Guesthouse in Terrebonne
4.98 out of 5 average rating, 103 reviewsModern lofted guest house
Apr 13 – 20
Guesthouse in Bend
5.0 out of 5 average rating, 16 reviewsBest area of Bend. Walk to river! Close to lakes.
Jan 15 – 22
Guesthouse in Bend
4.96 out of 5 average rating, 54 reviewsCozy Guesthouse with Large Kitchen
Aug 13 – 20
Guesthouse in Bend
4.96 out of 5 average rating, 52 reviewsArtisan's Woodsy Studio Cabin
Oct 8 – 15
Guesthouse in Bend
4.96 out of 5 average rating, 92 reviewsAdorable 1-bedroom 1930s farmhouse.
May 6 – 13
Guesthouse in Bend
5.0 out of 5 average rating, 3 reviewsTreetop Retreat on West Side. Walk to town.
Jan 10 – 17
Guesthouse in Sisters
4.7 out of 5 average rating, 169 reviewsDowntown Sisters Suite - Hot Tub - Dog Friendly
Oct 28 – Nov 4
Guest house rentals with a washer and dryer
Guesthouse in Bend
4.96 out of 5 average rating, 336 reviewsBlueSpruce Guesthouse-Walkable RiverTrail/Downtown
Oct 26 – Nov 2
Guesthouse in Bend
4.98 out of 5 average rating, 225 reviewsRanch Cottage: Desert, Forest, Horses, Hot Tub
Aug 22 – 29
Guesthouse in Bend
4.98 out of 5 average rating, 185 reviewsWest Hills Hideaway
Aug 13 – 20
Guesthouse in Bend
4.98 out of 5 average rating, 360 reviewsBend Ranch Guesthouse on 20 acres
Sep 16 – 23
Guesthouse in Redmond
4.83 out of 5 average rating, 230 reviewsThe Downtown Guesthouse
Aug 20 – 27
Guesthouse in Terrebonne
4.9 out of 5 average rating, 250 reviewsCompound Coziness...Terrebonne Guesthouse
Aug 25 – Sep 1
Guesthouse in Bend
4.98 out of 5 average rating, 173 reviewsHarvey House- Newly built w/ hot tub and backyard
Aug 25 – Sep 1
Guesthouse in Redmond
4.98 out of 5 average rating, 193 reviewsModern Downtown Cottage near Outdoor Adventure
Aug 26 – Sep 2
Quick stats about guesthouse rentals in Bend
Total rentals
70 properties
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
10K reviews
Nightly prices starting at
$40 before taxes and fees
Destinations to explore
- Eugene Vacation rentals
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