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Search results; 946 homes in Ashland

Guest favorite
Cottage in Ashland
Vineyard Cottage-Winery, Hot Tub, Privacy
1 bedroom, 1 bed, 1 private bath
Sep 27 – Oct 2
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4.92 out of 5 average rating, 263 reviews
Top guest favorite
Guesthouse in Ashland
Historic carriage house close to downtown Ashland
1 bedroom, 2 beds, 1 bath
Oct 19 – 24
4.98 out of 5 average rating, 120 reviews
Top guest favorite
Home in Talent
La Casetta Tuscana
2 bedrooms, 2 beds, 2 baths
Aug 29 – Sep 3
4.97 out of 5 average rating, 79 reviews
Top guest favorite
Guesthouse in Ashland
Countryman-Fox Carriage House
1 king bed, 1 bath
Nov 1 – 6
5.0 out of 5 average rating, 294 reviews
Guest favorite
Home in Ashland
Grandview of Ashland | Hot tub | Sauna | Firepit
2 bedrooms, 3 beds, 3 baths
Aug 26 – 31
4.97 out of 5 average rating, 39 reviews
Guest favorite
Cottage in Ashland
Charming very well appointed cottage !
1 bedroom, 1 king bed, 1 bath
Sep 26 – Oct 1
4.94 out of 5 average rating, 489 reviews
Top guest favorite
Apartment in Ashland
The Carriage House, Winner 2025 Best of Ashland!
1 bedroom, 2 beds, 1 bath
Aug 21 – 26
4.89 out of 5 average rating, 295 reviews
Guest favorite
Yurt in Ashland
Yurt in the mountains
1 bedroom, 1 bed, 1 bath
Aug 15 – 20
4.91 out of 5 average rating, 57 reviews
Home in Ashland
Ashland creekside home
3 bedrooms, 3 queen beds, 1 bath
Sep 20 – 25
4.69 out of 5 average rating, 74 reviews
Home in Ashland
Ashland creekside cottage
2 bedrooms, 3 beds, 1 bath
Aug 27 – Sep 1
4.61 out of 5 average rating, 97 reviews
Top guest favorite
Guesthouse in Ashland
Courtside Cottage - WalkScore 93 - Dog Friendly
2 beds, 1 bath
Aug 29 – Sep 3
4.98 out of 5 average rating, 276 reviews
Guest favorite
Cottage in Talent
Paschal Winery - Dream 1 Cottage
1 bedroom, 2 beds, 1 bath
Aug 18 – 23
4.93 out of 5 average rating, 72 reviews
Guest favorite
Camper/RV in Ashland
Nice 250sq ft camper in town
1 bedroom, 1 double bed, 1 bath
Aug 25 – 30
4.85 out of 5 average rating, 13 reviews
Top guest favorite
Guest suite in Ashland
RedTail Inn - Red McCall Suite | Sleeps up to 6
2 bedrooms, 3 beds, 1 bath
Oct 12 – 17
4.97 out of 5 average rating, 121 reviews
Guest favorite
Cabin in Ashland
Studio Cottage near downtown Ashland - Queen Bed!
1 bedroom, 1 queen bed, 1 bath
Sep 27 – Oct 2
4.95 out of 5 average rating, 603 reviews
Guest favorite
Cabin in Ashland
Cabin 48 at Hyatt Prairie
2 bedrooms, 3 beds, 1 bath
Aug 25 – 30
4.9 out of 5 average rating, 50 reviews
Guest favorite
Camper/RV in Ashland
Walk to town! Sweet Vintage Aloha
1 bedroom, 1 bed, 1 bath
Aug 26 – 31
4.84 out of 5 average rating, 87 reviews
Dome in Ashland
The Acorn dome w/ sauna
1 bedroom, 1 queen bed, 1 bath
Aug 17 – 22
4.8 out of 5 average rating, 230 reviews
Superhost
Cottage in Ashland
Bluemoon Vacation Rentals - Bluemoon Cottage
1 bedroom, 2 beds, 1 bath
Aug 21 – 26
4.67 out of 5 average rating, 39 reviews