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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
19–24 Sept
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4.93 out of 5 average rating, 260 reviews
Top guest favourite
Guest house in Ashland
Historic carriage house close to downtown Ashland
4.97 out of 5 average rating, 109 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Nov
Guest favourite
Cottage in Ashland
Charming very well appointed cottage !
4.95 out of 5 average rating, 473 reviews, 1 bedroom, 1 bed, 1 bathroom
31 Aug – 5 Sept
Top guest favourite
Guest house in Ashland
Courtside Cottage - WalkScore 93 - Dog Friendly
4.98 out of 5 average rating, 270 reviews, 2 beds, 1 bathroom
22–27 Jul
Superhost
Home in Ashland
Harmony Cottage - 2bd/1ba, 10 min from downtown!
4.77 out of 5 average rating, 154 reviews, 2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
Superhost
Dome in Ashland
The Acorn dome w/ sauna
4.8 out of 5 average rating, 214 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Aug
Guest favourite
Cabin in Ashland
Bluemoon Vacation Rentals - Cabin 52
4.84 out of 5 average rating, 112 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
Hotel in Ashland
Ashland Abode | Swim. Ski Nearby.
4.74 out of 5 average rating, 34 reviews, 1 bedroom, 2 beds, 1 bathroom
1–6 Jul
Top guest favourite
Apartment in Ashland
Plaza North Suite 203 Windsor
4.98 out of 5 average rating, 56 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
28 Aug – 2 Sept
Superhost
Camper van/Motorhome in Ashland
Walk to town! Sweet Vintage Aloha
4.84 out of 5 average rating, 74 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 Jul
Top guest favourite
Farm stay in Ashland
Kelly’s Farm 4 miles to Ashland
4.93 out of 5 average rating, 808 reviews, 1 bedroom, 2 beds, 1 bathroom
31 Aug – 5 Sept
Top guest favourite
Home in Ashland
Abram's Cottage
4.93 out of 5 average rating, 122 reviews, 2 bedrooms, 4 beds, 2 bathrooms
26–31 Oct
Top guest favourite
Place to stay in Ashland
Beautiful, peaceful & private King size apt
4.97 out of 5 average rating, 408 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Aug
Top guest favourite
Apartment in Ashland
Plaza North Suite 201 Alexander
5.0 out of 5 average rating, 69 reviews, 2 bedrooms, 3 beds, 2 bathrooms
12–17 Oct
Guest favourite
Cabin in Ashland
Whispering Pines Cabin near Hyatt Lake
4.91 out of 5 average rating, 43 reviews, 3 bedrooms, 6 beds, 1.5 bathrooms
19–24 Jul
Top guest favourite
Room in Ashland
Wood Hamlet - Noble Forest Room Private by DownTn
4.97 out of 5 average rating, 221 reviews, 1 queen bed, 1 bathroom
14–19 Aug
Top guest favourite
Cabin in Ashland
Studio Cottage near downtown Ashland - Queen Bed!
4.95 out of 5 average rating, 583 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Aug
Home in Ashland
Come Stroll-Inn downtown Ashland
New place to stay, 2 bedrooms, 2 beds, 2 bathrooms
27 Jul – 1 Aug
Top guest favourite
Guest suite in Ashland
The Billiard Room, Winner 2025 Best of Ashland!
4.88 out of 5 average rating, 206 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Aug