Guesthouse holiday rentals in Ashland
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Top-rated Guesthouses in Ashland
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
Holiday 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
21–28 May
Guesthouse in Medford
4.98 out of 5 average rating, 427 reviewsComice Valley Inn (Sanitized Daily)
2–9 Oct
Guesthouse in Medford
4.85 out of 5 average rating, 118 reviewsLotus 2-Peaceful-Central Location-W/D-Walk to Park
24 Jun – 1 Jul
Guesthouse in Grants Pass
4.96 out of 5 average rating, 341 reviewsQueen Lady Vacation Rental pet friendly.
6–13 Oct
Guesthouse in Grants Pass
4.94 out of 5 average rating, 430 reviewsSweet Vintage Cottage steps from Rogue River
18–25 Mar
Guesthouse in Medford
4.95 out of 5 average rating, 66 reviewsRoxy Ann Retreat - Large Luxury Carriage House
26 Aug – 2 Sep
Guesthouse in Gold Hill
4.98 out of 5 average rating, 83 reviewsRogue River Guesthouse: Rural river views near I-5
25 Jan – 1 Feb
Guesthouse in Medford
4.67 out of 5 average rating, 105 reviewsMillion Dollar View No city tax! Huge 4k tvs
6–13 Jul
Guesthouses with a patio
Guesthouse in Ashland
4.98 out of 5 average rating, 114 reviewsCourtside Cottage - WalkScore 93 - Dog Friendly
25 Sep – 2 Oct
Guesthouse in Ashland
5.0 out of 5 average rating, 57 reviewsCountryman-Fox Carriage House
5–12 Feb
Guesthouse in Ashland
4.93 out of 5 average rating, 40 reviewsThe Poets' Inspiration Cottage
8–15 Oct
Guesthouse in Ashland
5.0 out of 5 average rating, 80 reviewsC Street Station Cottage
21–28 Sep
Guesthouse in Medford
5.0 out of 5 average rating, 42 reviewsSwiss Arbor Guest House
29 Jun – 6 Jul
Guesthouse in Medford
4.8 out of 5 average rating, 10 reviewsLuxe Cottage La Havre House-private pool & hot tub
31 Jul – 7 Aug
Guesthouse in Grants Pass
4.81 out of 5 average rating, 85 reviewsCozy Mountain Hillside Cabin & Woodland Paradise
27 Nov – 4 Dec
Guesthouse in Grants Pass
4.99 out of 5 average rating, 69 reviewsSpacious upstairs studio with kitchenette & 1 bath
8–15 Apr
Guest house rentals with a washing machine and dryer
Guesthouse in Medford
4.97 out of 5 average rating, 131 reviewsThe Loft at Highcrest
27 Feb – 6 Mar
Guesthouse in Medford
4.95 out of 5 average rating, 166 reviewsModern, pet-friendly, private - EV charger level 2
22–29 Nov
Guesthouse in Central Point
4.96 out of 5 average rating, 505 reviewsHygge Stay. Pet friendly* private and cozy.
16–23 Aug
Guesthouse in Grants Pass
4.98 out of 5 average rating, 205 reviewsSand Creek Cottage
8–15 Nov
Guesthouse in Medford
4.96 out of 5 average rating, 289 reviewsCabo Cottage, private guest house.
15–22 Jul
Guesthouse in Central Point
4.92 out of 5 average rating, 130 reviewsHot tub - Modern - Relaxing - Private - Clean
12–19 Aug
Guesthouse in Medford
4.99 out of 5 average rating, 193 reviewsNewer, quiet, private cottage
12–19 Jun
Guesthouse in Ashland
4.78 out of 5 average rating, 86 reviewsEast Main Downtown Bungalow
4–11 Sep
Quick stats about guesthouse rentals in Ashland
Total rentals
30 properties
Popular amenities
Kitchen, Wi-Fi and Pool
Wi-Fi availability
30 properties include access to Wi-Fi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Total number of reviews
3.2K reviews
Nightly prices starting at
$84 NZD before taxes and fees
Destinations to explore
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