Guesthouse vacation rentals in Ashland
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouses in Ashland
Guests agree: these guesthouses 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 Ashland guesthouses
Family-friendly guesthouses
Guesthouse in Medford
4.92 out of 5 average rating, 344 reviewsThe Greenwood Villa
May 21 – 28
Guesthouse in Medford
4.98 out of 5 average rating, 428 reviewsComice Valley Inn (Sanitized Daily)
Oct. 21 – 28
Guesthouse in Medford
4.85 out of 5 average rating, 118 reviewsLotus 2-Peaceful-Central Location-W/D-Walk to Park
Oct. 14 – 21
Guesthouse in Grants Pass
4.96 out of 5 average rating, 341 reviewsQueen Lady Vacation Rental pet friendly.
Oct. 6 – 13
Guesthouse in Grants Pass
4.94 out of 5 average rating, 430 reviewsSweet Vintage Cottage steps from Rogue River
Jan. 31 – Feb. 7
Guesthouse in Medford
4.95 out of 5 average rating, 66 reviewsRoxy Ann Retreat - Large Luxury Carriage House
May 7 – 14
Guesthouse in Medford
4.67 out of 5 average rating, 106 reviewsMillion Dollar View No city tax! Huge 4k tvs
Jul. 6 – 13
Guesthouse in Gold Hill
4.98 out of 5 average rating, 83 reviewsRogue River Guesthouse: Rural river views near I-5
Sep. 17 – 24
Guesthouses with a patio
Guesthouse in Ashland
4.98 out of 5 average rating, 114 reviewsCourtside Cottage - WalkScore 93 - Dog Friendly
Sep. 25 – Oct. 2
Guesthouse in Ashland
5.0 out of 5 average rating, 59 reviewsCountryman-Fox Carriage House
Dec. 1 – 8
Guesthouse in Ashland
4.93 out of 5 average rating, 41 reviewsThe Poets' Inspiration Cottage
Oct. 8 – 15
Guesthouse in Ashland
5.0 out of 5 average rating, 80 reviewsC Street Station Cottage
Oct. 28 – Nov. 4
Guesthouse in Medford
5.0 out of 5 average rating, 42 reviewsSwiss Arbor Guest House
Jul. 8 – 15
Guesthouse in Medford
4.8 out of 5 average rating, 10 reviewsLuxe Cottage La Havre House-private pool & hot tub
Jul. 6 – 13
Guesthouse in Grants Pass
4.81 out of 5 average rating, 85 reviewsCozy Mountain Hillside Cabin & Woodland Paradise
Oct. 1 – 8
Guesthouse in Ashland
4.92 out of 5 average rating, 25 reviewsSilver Frog Guesthouse- downtown Ashland 'hood
Aug. 31 – Sep. 7
Guesthouse rentals with a washer and dryer
Guesthouse in Medford
4.97 out of 5 average rating, 131 reviewsThe Loft at Highcrest
Aug. 22 – 29
Guesthouse in Medford
4.95 out of 5 average rating, 166 reviewsModern, pet-friendly, private - EV charger level 2
Dec. 31 – Jan. 7
Guesthouse in Medford
4.96 out of 5 average rating, 289 reviewsCabo Cottage, private guest house.
Jul. 15 – 22
Guesthouse in Central Point
4.96 out of 5 average rating, 505 reviewsHygge Stay. Pet friendly* private and cozy.
Aug. 16 – 23
Guesthouse in Grants Pass
4.98 out of 5 average rating, 205 reviewsSand Creek Cottage
Aug. 14 – 21
Guesthouse in Central Point
4.92 out of 5 average rating, 130 reviewsHot tub - Modern - Relaxing - Private - Clean
Nov. 3 – 10
Guesthouse in Medford
4.99 out of 5 average rating, 193 reviewsNewer, quiet, private cottage
Jun. 16 – 23
Guesthouse in Ashland
4.76 out of 5 average rating, 88 reviewsEast Main Downtown Bungalow
Sep. 4 – 11
Quick stats about guesthouse rentals in Ashland
Total rentals
30 properties
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Total number of reviews
3.2K reviews
Nightly prices starting at
$68 CAD before taxes and fees
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