Search results; Over 1,000 homes in Ashland

Top guest favourite
Cottage in Ashland
Vineyard Cottage-Winery, Hot Tub, Privacy
1 bedroom, 1 bed, 1 private bathroom
23–28 Aug
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4.93 out of 5 average rating, 259 reviews
Top guest favourite
Guest house in Ashland
Historic carriage house close to downtown Ashland
1 bedroom, 2 beds, 1 bathroom
2–7 Nov
4.97 out of 5 average rating, 107 reviews
Top guest favourite
Cabin in Ashland
Cozy Ashland Farm Cabin
1 queen bed, 1 bathroom
22–27 Aug
4.96 out of 5 average rating, 847 reviews
Superhost
Home in Ashland
Harmony Cottage - 2bd/1ba, 10 min from downtown!
2 bedrooms, 2 queen beds, 1 bathroom
26–31 Jul
4.77 out of 5 average rating, 154 reviews
Home in Medford
Modern Pet-Friendly Stay | Near Downtown Medford
2 bedrooms, 2 queen beds, 1 bathroom
11–16 Jul
New place to stay
Superhost
Tiny home in Ashland
Walk to town! Cozy Forest Teeny House
1 bedroom, 1 bed, 1 bathroom
5–10 Jul
4.81 out of 5 average rating, 186 reviews
Guest favourite
Cabin in Ashland
Whispering Pines Cabin near Hyatt Lake
3 bedrooms, 6 beds, 1.5 bathrooms
19–24 Jul
4.91 out of 5 average rating, 43 reviews
Top guest favourite
Guest suite in Ashland
Eco-friendly Woodland Retreat
2 bedrooms, 3 beds, 1 bathroom
22–27 Aug
4.98 out of 5 average rating, 40 reviews
Guest favourite
Yurt in Ashland
Yurt in the mountains
1 bedroom, 1 bed, 1 bathroom
6–11 Jul
4.95 out of 5 average rating, 43 reviews
Top guest favourite
Home in Ashland
The Aloha House - Hot Tub - Pool
2 bedrooms, 2 king beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 149 reviews
Guest favourite
Home in Talent
Meadowsweet Farm | Hot Tub | Outdoor Kitchen
7 bedrooms, 11 beds, 3 bathrooms
10–15 Aug
5.0 out of 5 average rating, 18 reviews
Superhost
Room in Ashland
Cozy Sunset Loft Walk to town
1 queen bed, 1 bathroom
12–17 Jul
4.86 out of 5 average rating, 169 reviews
Superhost
Home in Ashland
Ashland creekside cottage
2 bedrooms, 3 beds, 1 bathroom
1–6 Aug
4.65 out of 5 average rating, 83 reviews
Guest favourite
Farm stay in Ashland
Ashland Lavender Estate
4 bedrooms, 6 beds, 3 bathrooms
12–17 Sept
4.94 out of 5 average rating, 35 reviews
Farm stay in Ashland
Peace and Joy Mini Farm
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Aug
4.7 out of 5 average rating, 207 reviews
Top guest favourite
Cottage in Ashland
Sweet Breeze Bungalow
1 bedroom, 2 beds, 1 bathroom
12–17 Sept
4.98 out of 5 average rating, 128 reviews
Guest favourite
Home in Ashland
Grandview of Ashland | Hot tub | Sauna | Firepit
2 bedrooms, 3 beds, 3 bathrooms
24–29 Jul
4.97 out of 5 average rating, 35 reviews
Guest favourite
Home in Ashland
Mountain Ave House by WanderLodges
3 bedrooms, 3 beds, 2 bathrooms
31 Jul – 5 Aug
4.92 out of 5 average rating, 62 reviews
Top guest favourite
Bungalow in Ashland
Hanna's House | Downtown Retreat, Steps to OSF
1 bedroom, 2 beds, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 38 reviews