Guesthouse vacation rentals in Ashland
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Top-rated guesthouse rentals in Ashland
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 Ashland guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Central Point
BEE WELL Organic Spa Garden Studio
Guesthouse in Medford
The Greenwood Villa
Guesthouse in Medford
Lotus 2-Peaceful-Well Stocked-W/D-Walk to Park
Guesthouse in Medford
Comice Valley Apartment
Guesthouse in Grants Pass
Queen Lady Vacation Rental pet friendly.
Guesthouse in Grants Pass
Sweet Vintage Cottage steps from Rogue River
Guesthouse in Medford
Roxy Ann Retreat - Large Luxury Carriage House
Guesthouse in Medford
Million Dollar View No city tax! Huge 4k tvs
Guest house rentals with a patio
Guesthouse in Ashland
Modern Airy Retreat - Views, Walk to Everything
Guesthouse in Ashland
Countryman-Fox Carriage House
Guesthouse in Ashland
The Poets' Inspiration Cottage
Guesthouse in Grants Pass
New Modern Cottage on the Rogue
Guesthouse in Medford
Swiss Arbor Guest House
Guesthouse in Ashland
C Street Station Cottage
Guesthouse in Ashland
Silver Frog Guesthouse- downtown Ashland 'hood
Guesthouse in Medford
Adorable guest house with hot tub.
Guest house rentals with a washer and dryer
Guesthouse in Medford
The Loft at Highcrest
Guesthouse in Central Point
Hygge Stay. Pet friendly* private and cozy.
Guesthouse in Central Point
Hot tub - Modern - Relaxing - Private - Clean
Guesthouse in Ashland
JJ's Loft | Downtown | Large Deck | Kitchenette
Guesthouse in Medford
Cabo Cottage, private guest house.
Guesthouse in Medford
Newer, quiet, private cottage
Guesthouse in Ashland
Guesthouse in Ashland 4 blocks from the OSF
Guesthouse in Ashland
East Main Downtown Bungalow
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
$50 before taxes and fees
Destinations to explore
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- Guesthouse rentals United States
- House rentals United States
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- Guesthouse rentals Oregon
- Rentals with a fireplace Ashland
- Kid-friendly rentals Ashland
- Cabin rentals Ashland
- Cottage rentals Ashland
- Rentals with a fire pit Ashland
- Rentals with outdoor seating Ashland
- Private suite rentals Ashland
- Rentals with an EV charger Ashland
- Rentals with breakfast Ashland
- Rentals with a washer and dryer Ashland
- Pet-friendly rentals Ashland
- Monthly Rentals Ashland
- Family-friendly rentals Ashland
- Rentals with a hot tub Ashland
- House rentals Ashland
- Rentals with pools Ashland
- Rentals with a patio Ashland
- Apartment rentals Ashland
- Guesthouse rentals Medford
- House rentals Medford
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- 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
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- Pet-Friendly Vacation Rentals United States
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- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom