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Search results; 961 homes in Ashland

Top guest favourite
Guest house in Ashland
JJ's Loft | Downtown | Large Deck | Kitchenette
1 bedroom, 1 bed, 1 private bathroom
29 Aug – 3 Sept
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4.95 out of 5 average rating, 136 reviews
Top guest favourite
Guest house in Ashland
Historic carriage house close to downtown Ashland
4.97 out of 5 average rating, 113 reviews, 1 bedroom, 2 beds, 1 bathroom
19–24 Sept
Dome in Ashland
The Acorn dome w/ sauna
4.8 out of 5 average rating, 221 reviews, 1 bedroom, 1 bed, 1 bathroom
17–22 Aug
Top guest favourite
Guest house in Ashland
Countryman-Fox Carriage House
5.0 out of 5 average rating, 288 reviews, 1 bed, 1 bathroom
18–23 Oct
Guest favourite
Home in Ashland
Pioneer Vacation Rentals - Pioneer South
4.92 out of 5 average rating, 60 reviews, 3 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
Top guest favourite
Cottage in Ashland
Sweet Breeze Bungalow
4.98 out of 5 average rating, 135 reviews, 1 bedroom, 2 beds, 1 bathroom
4–9 Sept
Top guest favourite
Room in Ashland
Wood Hamlet - Noble Forest Room Private by DownTn
4.97 out of 5 average rating, 222 reviews, 1 queen bed, 1 bathroom
31 Aug – 5 Sept
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
Guest suite in Ashland
Eco-friendly Woodland Retreat
4.98 out of 5 average rating, 42 reviews, 2 bedrooms, 3 beds, 1 bathroom
22–27 Aug
Superhost
Room in Ashland
Lovely light filled room with porch
4.7 out of 5 average rating, 902 reviews, 1 queen bed, 1 bathroom
20–25 Aug
Guest favourite
Guest house in Ashland
Neil Creek Cottage
4.93 out of 5 average rating, 152 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Aug
Top guest favourite
Home in Medford
New 1BR House | Hot Tub | W/D | Full Kitchen
4.99 out of 5 average rating, 72 reviews, 1 bedroom, 2 beds, 1 bathroom
13–18 Aug
Top guest favourite
Guest suite in Ashland
Wood Hamlet - Miro Room, walk to town
4.97 out of 5 average rating, 233 reviews, 1 bedroom, 1 bed, 1 bathroom
28 Sept – 3 Oct
Top guest favourite
Home in Ashland
Creekside Retreat Close to Town
4.97 out of 5 average rating, 247 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
22–27 Oct
Guest favourite
Home in Ashland
Grandview of Ashland | Hot tub | Sauna | Firepit
4.97 out of 5 average rating, 36 reviews, 2 bedrooms, 3 beds, 3 bathrooms
8–13 Aug
Top guest favourite
Cabin in Ashland
Studio Cottage near downtown Ashland - Queen Bed!
4.95 out of 5 average rating, 589 reviews, 1 bedroom, 1 bed, 1 bathroom
3–8 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
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
26–31 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