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Search results; 963 homes in Ashland

Guest favourite
Cottage in Ashland
Vineyard Cottage-Winery, Hot Tub, Privacy
1 bedroom, 1 bed, 1 private bathroom
4–9 Oct
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4.93 out of 5 average rating, 261 reviews
Top guest favourite
Cabin in Ashland
Cozy Ashland Farm Cabin
4.96 out of 5 average rating, 853 reviews, 1 bed, 1 bathroom
31 Aug – 5 Sept
Top guest favourite
Place to stay in Ashland
Beautiful, peaceful & private King size apt
4.97 out of 5 average rating, 413 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
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
Home in Medford
Cozy Cottage
New place to stay, 2 bedrooms, 2 beds, 1.5 bathrooms
17–22 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
Guest favourite
Farm stay in Ashland
Kelly’s Carriage House 4 miles from Ashland
4.97 out of 5 average rating, 376 reviews, 1 bedroom, 2 beds, 1 bathroom
20–25 Sept
Top guest favourite
Home in Ashland
The Aloha House - Hot Tub - Pool
4.96 out of 5 average rating, 155 reviews, 2 bedrooms, 2 beds, 2 bathrooms
27 Sept – 2 Oct
Guest favourite
Room in Ashland
Château Herbe ~ Vienna Room
4.9 out of 5 average rating, 115 reviews, 1 king bed, 1 bathroom
31 Jul – 5 Aug
Dome in Ashland
The Acorn dome w/ sauna
4.8 out of 5 average rating, 220 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Guest favourite
Guest suite in Ashland
RedTail Inn - Louisa Suite | Hot Tub |DWTN
4.91 out of 5 average rating, 74 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Top guest favourite
Room in Talent
1-bedroom on a small country farm.
4.94 out of 5 average rating, 298 reviews, 2 beds, 1 bathroom
26–31 Jul
Guest favourite
Flat in Ashland
Beautiful Ashland Flat
4.82 out of 5 average rating, 17 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Guest house in Ashland
Countryman-Fox Carriage House
5.0 out of 5 average rating, 285 reviews, 1 bed, 1 bathroom
18–23 Oct
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
11–16 Aug
Guest favourite
Cabin in Ashland
Cabin 48 at Hyatt Prairie
4.91 out of 5 average rating, 46 reviews, 2 bedrooms, 3 beds, 1 bathroom
17–22 Jul
Guest favourite
Home in Talent
Beautiful 3-bedroom Family House
4.86 out of 5 average rating, 42 reviews, 3 bedrooms, 3 beds, 2 bathrooms
28 Aug – 2 Sept
Top guest favourite
Guest suite in Ashland
The Billiard Room, Winner 2025 Best of Ashland!
4.89 out of 5 average rating, 209 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Top guest favourite
Apartment in Ashland
Plaza North Suite 203 Windsor
4.98 out of 5 average rating, 58 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
28 Aug – 2 Sept