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Search results; 961 homes in Ashland

Top guest favourite
Cottage in Ashland
Victorian Garden Carriage House
2 bedrooms, 2 beds, 1 private bathroom
17–22 Oct
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4.97 out of 5 average rating, 508 reviews
Top guest favourite
Cabin in Ashland
Cozy Ashland Farm Cabin
4.96 out of 5 average rating, 853 reviews, 1 bed, 1 bathroom
2–7 Oct
Home in Medford
Viewtacular Estate House, Pool, Hot tub & Sauna!
New place to stay, 4 bedrooms, 4 beds, 3.5 bathrooms
19–24 Jul
Guest favourite
Camper van/Motorhome in Ashland
Walk to town! The Deep Blue Metallic Dream Machine
4.86 out of 5 average rating, 197 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Top guest favourite
Guest house in Ashland
Historic carriage house close to downtown Ashland
4.97 out of 5 average rating, 112 reviews, 1 bedroom, 2 beds, 1 bathroom
10–15 Nov
Top guest favourite
Room in Ashland
Cozy/rural close to town
4.9 out of 5 average rating, 944 reviews, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
Top guest favourite
Place to stay in Ashland
Beautiful, peaceful & private King size apt
4.97 out of 5 average rating, 414 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Cottage in Talent
Paschal Winery - Dream 1 Cottage
4.93 out of 5 average rating, 71 reviews, 1 bedroom, 2 beds, 1 bathroom
15–20 Aug
Tiny home in Ashland
Ashland tiny home and barrel sauna
4.77 out of 5 average rating, 279 reviews, 1 bedroom, 1 bed, 1 bathroom
28 Jul – 2 Aug
Superhost
Room in Ashland
Lovely light filled room with porch
4.69 out of 5 average rating, 900 reviews, 1 queen bed, 1 bathroom
20–25 Aug
Home in Medford
Cozy Cottage
New place to stay, 2 bedrooms, 2 beds, 1.5 bathrooms
18–23 Jul
Superhost
Home in Ashland
Harmony Cottage - 2bd/1ba, 10 min from downtown!
4.78 out of 5 average rating, 157 reviews, 2 bedrooms, 2 beds, 1 bathroom
21–26 Aug
Top guest favourite
Home in Ashland
The Aloha House - Hot Tub - Pool
4.96 out of 5 average rating, 156 reviews, 2 bedrooms, 2 beds, 2 bathrooms
27 Sept – 2 Oct
Guest favourite
Cabin in Ashland
Cabin 48 at Hyatt Prairie
4.9 out of 5 average rating, 49 reviews, 2 bedrooms, 3 beds, 1 bathroom
17–22 Jul
Top guest favourite
Guest suite in Ashland
The Billiard Room, Winner 2025 Best of Ashland!
4.89 out of 5 average rating, 210 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Superhost
Yurt in Ashland
Yurt in the mountains
4.9 out of 5 average rating, 50 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Jul
Top guest favourite
Home in Medford
New 1BR House | Hot Tub | W/D | Full Kitchen
4.99 out of 5 average rating, 71 reviews, 1 bedroom, 2 beds, 1 bathroom
13–18 Aug
Top guest favourite
Guest house in Ashland
JJ's Loft | Downtown | Large Deck | Kitchenette
4.95 out of 5 average rating, 135 reviews, 1 bedroom, 1 bed, 1 bathroom
29 Aug – 3 Sept
Superhost
Guest house in Ashland
The Milkhouse
4.78 out of 5 average rating, 9 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Jul