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
Sep 15 – 22
Guesthouse in Bend
4.98 out of 5 average rating, 251 reviewsCountry Apartment, Tumalo 2BR
May 28 – Jun 4
Guesthouse in Bend
4.96 out of 5 average rating, 237 reviewsQuiet peacful country living close to everything!
Jun 11 – 18
Guesthouse in Bend
4.94 out of 5 average rating, 207 reviewsLarge Craftsman Studio
Aug 30 – Sep 6
Guesthouse in Bend
4.95 out of 5 average rating, 675 reviewsCozy Bookworm's Retreat in Bend
Jan 22 – 29
Guesthouse in Bend
4.85 out of 5 average rating, 484 reviewsCozy & Convenient Downtown Cottage
Nov 25 – Dec 2
Guesthouse in Bend
4.8 out of 5 average rating, 274 reviewsThe Bivouac of Bend
Oct 14 – 21
Guesthouse in Bend
4.96 out of 5 average rating, 54 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, 107 reviewsPonderosa Pines Bunkhouse - Dog friendly ADU
Dec 17 – 24
Guesthouse in Terrebonne
4.98 out of 5 average rating, 102 reviewsModern lofted guest house
Apr 15 – 22
Guesthouse in Bend
5.0 out of 5 average rating, 31 reviewsMtn Modern 1 BR Craftsman, walk to Old Mill
Oct 27 – Nov 3
Guesthouse in Bend
4.96 out of 5 average rating, 52 reviewsArtisan's Woodsy Studio Cabin
Oct 3 – 10
Guesthouse in Bend
4.96 out of 5 average rating, 54 reviewsCozy Guesthouse with Large Kitchen
Aug 21 – 28
Guesthouse in Bend
5.0 out of 5 average rating, 22 reviewsNEW Tranquil Retreat On Canal
Oct 9 – 16
Guesthouse in Bend
5.0 out of 5 average rating, 3 reviewsTreetop Retreat on West Side. Walk to town.
Dec 29 – Jan 5
Guesthouse in Sisters
4.71 out of 5 average rating, 168 reviewsDowntown Sisters Suite - Hot Tub - Dog Friendly
Oct 23 – 30
Guest house rentals with a washer and dryer
Guesthouse in Terrebonne
4.84 out of 5 average rating, 182 reviews15 min from SmithRock pets allowed affordable spot
May 14 – 19
Guesthouse in Bend
4.94 out of 5 average rating, 539 reviewsPrivate apt. nestled in the Ponderosa Pines
Aug 7 – 14
Guesthouse in Bend
4.96 out of 5 average rating, 336 reviewsBlueSpruce Guesthouse-Walkable RiverTrail/Downtown
Oct 22 – 29
Guesthouse in Bend
4.98 out of 5 average rating, 223 reviewsRanch Cottage: Desert, Forest, Horses, Hot Tub
Aug 18 – 25
Guesthouse in Bend
4.98 out of 5 average rating, 185 reviewsWest Hills Hideaway
Sep 29 – Oct 6
Guesthouse in Redmond
4.98 out of 5 average rating, 192 reviewsModern Downtown Cottage near Outdoor Adventure
Sep 11 – 18
Guesthouse in Bend
4.85 out of 5 average rating, 102 reviewsWHOLE HOUSE! Tiny Home on Bend's East Side
Dec 11 – 18
Guesthouse in Redmond
4.84 out of 5 average rating, 228 reviewsThe Downtown Guesthouse
Oct 14 – 21
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
€ 37 before taxes and fees
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