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Search results; 945 homes in Ashland

Guest favourite
Cottage in Ashland
Sherwin Cottage
2 bedrooms, 3 beds, 2 private bathrooms
26–31 Oct
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4.94 out of 5 average rating, 47 reviews
Guest favourite
Home in Ashland
Grandview of Ashland | Hot tub | Sauna | Firepit
2 bedrooms, 3 beds, 3 bathrooms
26–31 Aug
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Guest house in Ashland
Historic carriage house close to downtown Ashland
1 bedroom, 2 beds, 1 bathroom
19–24 Oct
4.98 out of 5 average rating, 120 reviews
Top guest favourite
Home in Talent
La Casetta Tuscana
2 bedrooms, 2 beds, 2 bathrooms
29 Aug – 3 Sept
4.97 out of 5 average rating, 79 reviews
Guest favourite
Camper van/Motorhome in Ashland
Walk to town! Sweet Vintage Aloha
1 bedroom, 1 bed, 1 bathroom
26–31 Aug
4.84 out of 5 average rating, 87 reviews
Top guest favourite
Guest house in Ashland
Courtside Cottage - WalkScore 93 - Dog Friendly
2 beds, 1 bathroom
29 Aug – 3 Sept
4.98 out of 5 average rating, 276 reviews
Top guest favourite
Place to stay in Ashland
Beautiful, peaceful & private King size apt
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 425 reviews
Guest favourite
Cabin in Ashland
Studio Cottage near downtown Ashland - Queen Bed!
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 603 reviews
Dome in Ashland
The Acorn dome w/ sauna
1 bedroom, 1 queen bed, 1 bathroom
17–22 Aug
4.8 out of 5 average rating, 230 reviews
Guest favourite
Cottage in Ashland
Charming very well appointed cottage !
1 bedroom, 1 king bed, 1 bathroom
26 Sept – 1 Oct
4.94 out of 5 average rating, 489 reviews
Top guest favourite
Guest house in Ashland
Countryman-Fox Carriage House
1 king bed, 1 bathroom
1–6 Nov
5.0 out of 5 average rating, 294 reviews
Top guest favourite
Guest suite in Medford
Parkside East Medford Studio (Easy I-5 Access)
2 beds, 1 bathroom
15–20 Aug
4.99 out of 5 average rating, 289 reviews
Guest favourite
Flat in Ashland
Beautiful Ashland Flat
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.82 out of 5 average rating, 22 reviews
Top guest favourite
Flat in Ashland
The Carriage House, Winner 2025 Best of Ashland!
1 bedroom, 2 beds, 1 bathroom
21–26 Aug
4.89 out of 5 average rating, 295 reviews
Superhost
Room in Ashland
Lovely light filled room with porch
1 queen bed, 1 bathroom
10–15 Sept
4.7 out of 5 average rating, 910 reviews
Guest favourite
Yurt in Ashland
Yurt in the mountains
1 bedroom, 1 bed, 1 bathroom
15–20 Aug
4.91 out of 5 average rating, 57 reviews
Guest favourite
Home in Medford
New 1BR House | Hot Tub | W/D | Full Kitchen
1 bedroom, 2 beds, 1 bathroom
22–27 Aug
4.93 out of 5 average rating, 84 reviews
Top guest favourite
Guest house in Ashland
Charming cottage, walk to town.
1 bedroom, 2 beds, 1.5 bathrooms
18–23 Oct
4.98 out of 5 average rating, 562 reviews
Guest favourite
Room in Ashland
Château Herbe ~ Vienna Room
1 king bed, 1 bathroom
31 Aug – 5 Sept
4.89 out of 5 average rating, 121 reviews