Guesthouse accommodation & holiday rentals in Ashland
Find and book unique guesthouse accommodation & rentals on Airbnb
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
11 – 18 July
Guesthouse in Medford
4.98 out of 5 average rating, 428 reviewsComice Valley Inn (Sanitized Daily)
30 July – 6 Aug
Guesthouse in Medford
4.85 out of 5 average rating, 118 reviewsLotus 2-Peaceful-Well Stocked-W/D-Walk to Park
4 – 11 Aug
Guesthouse in Grants Pass
4.96 out of 5 average rating, 341 reviewsQueen Lady Vacation Rental pet friendly.
27 Apr – 4 May
Guesthouse in Grants Pass
4.94 out of 5 average rating, 430 reviewsSweet Vintage Cottage steps from Rogue River
10 – 17 June
Guesthouse in Medford
4.95 out of 5 average rating, 66 reviewsRoxy Ann Retreat - Large Luxury Carriage House
4 – 11 June
Guesthouse in Medford
4.67 out of 5 average rating, 106 reviewsMillion Dollar View No city tax! Huge 4k tvs
7 – 14 June
Guesthouse in Gold Hill
4.98 out of 5 average rating, 83 reviewsRogue River Guesthouse: Rural river views near I-5
15 – 22 Feb
Guesthouses with a patio
Guesthouse in Ashland
4.98 out of 5 average rating, 114 reviewsCourtside Cottage - WalkScore 93 - Dog Friendly
25 Sept – 2 Oct
Guesthouse in Ashland
5.0 out of 5 average rating, 59 reviewsCountryman-Fox Carriage House
8 – 15 Mar
Guesthouse in Ashland
4.93 out of 5 average rating, 41 reviewsThe Poets' Inspiration Cottage
3 – 10 Oct
Guesthouse in Ashland
5.0 out of 5 average rating, 80 reviewsC Street Station Cottage
23 Feb – 2 Mar
Guesthouse in Medford
5.0 out of 5 average rating, 42 reviewsSwiss Arbor Guest House
11 – 18 July
Guesthouse in Medford
4.8 out of 5 average rating, 10 reviewsLuxe Cottage La Havre House-private pool & hot tub
13 – 20 Oct
Guesthouse in Jacksonville
4.89 out of 5 average rating, 27 reviewsSerenity Canyon Cottage
15 – 22 Sept
Guesthouse in Ashland
4.92 out of 5 average rating, 25 reviewsSilver Frog Guesthouse- downtown Ashland 'hood
10 – 17 Dec
Guest house rentals with a washing machine and dryer
Guesthouse in Medford
4.97 out of 5 average rating, 131 reviewsThe Loft at Highcrest
31 Oct – 7 Nov
Guesthouse in Medford
4.96 out of 5 average rating, 289 reviewsCabo Cottage, private guest house.
22 – 29 Sept
Guesthouse in Central Point
4.96 out of 5 average rating, 506 reviewsHygge Stay. Pet friendly* private and cozy.
3 – 10 Sept
Guesthouse in Grants Pass
4.98 out of 5 average rating, 205 reviewsSand Creek Cottage
17 – 24 Aug
Guesthouse in Ashland
4.94 out of 5 average rating, 109 reviewsJJ's Loft | Downtown | Large Deck | Kitchenette
4 – 11 Apr
Guesthouse in Central Point
4.92 out of 5 average rating, 130 reviewsHot tub - Modern - Relaxing - Private - Clean
6 – 13 Nov
Guesthouse in Medford
4.99 out of 5 average rating, 193 reviewsNewer, quiet, private cottage
26 June – 3 July
Guesthouse in Ashland
4.76 out of 5 average rating, 88 reviewsEast Main Downtown Bungalow
8 – 15 Oct
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
$77 AUD before taxes and fees
Destinations to explore
- Mount Shasta Accommodation & holiday rentals
- Medford Accommodation & holiday rentals
- Crater Lake Holiday rentals
- Lake of the Woods Holiday rentals
- Crescent City Holiday rentals
- Brookings Accommodation & holiday rentals
- Grants Pass Accommodation & holiday rentals
- Klamath Falls Accommodation & holiday rentals
- Gold Beach Accommodation & holiday rentals
- Roseburg Holiday rentals
- Weed Holiday rentals
- Portland Accommodation & holiday rentals
- House rentals United States
- Guesthouse rentals United States
- Guesthouse rentals Oregon
- House rentals Oregon
- Apartment rentals Ashland
- Private suite rentals Ashland
- Rentals with breakfast Ashland
- Rentals with a fire pit Ashland
- Kid-friendly rentals Ashland
- Rentals with pools Ashland
- Rentals with a fireplace Ashland
- House rentals Ashland
- Rentals with a hot tub Ashland
- Rentals with outdoor seating Ashland
- Monthly Rentals Ashland
- Pet-friendly rentals Ashland
- Cottage rentals Ashland
- Cabin rentals Ashland
- Family-friendly rentals Ashland
- Rentals with a patio Ashland
- Rentals with a washing machine and dryer Ashland
- House rentals Mount Shasta
- House rentals Medford
- Guesthouse rentals Medford
- Guesthouse rentals Jackson County
- House rentals Jackson County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom