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Search results; Over 1,000 homes in Ashland

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Top guest favourite
Cabin in Town of Ashland
Luxury Cabin Retreat - 7 Mins to Windham
3 bedrooms, 8 beds, 2 private bathrooms
17–22 Sept
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5.0 out of 5 average rating, 32 reviews
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Top guest favourite
Cabin in Windham
Cozy Creekside Cabin | 5 Mins to Windham Mt!
3 bedrooms, 4 beds, 1 bathroom
25–30 Oct
4.95 out of 5 average rating, 226 reviews
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Guest favourite
Cabin in Windham
Dream cabin
5 bedrooms, 7 beds, 3 bathrooms
19–24 Oct
4.89 out of 5 average rating, 62 reviews
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Guest favourite
Home in Windham
Creekside Lodge | 7 Min to Skiing | Sleeps 12
4 bedrooms, 8 beds, 3 bathrooms
28 Sept – 3 Oct
4.93 out of 5 average rating, 72 reviews
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Home in Prattsville
Our Ski House
4 bedrooms, 6 queen beds, 2.5 bathrooms
22–27 Sept
5.0 out of 5 average rating, 32 reviews
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Top guest favourite
Cabin in Windham
Catskills Designer Retreat near Hiking + Swimming
4 bedrooms, 4 beds, 2 bathrooms
17–22 Sept
4.97 out of 5 average rating, 142 reviews
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Home in Windham
Entire Magda Cabin XL! Sauna! Hot Tub!
7 bedrooms, 13 beds, 5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Home in Prattsville
10 min to Windham! 20 min to Hunter! EV charger!
3 bedrooms, 8 beds, 3 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 44 reviews
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Top guest favourite
Home in Windham
Private cabin in the Catskills
2 bedrooms, 2 queen beds, 1 bathroom
11–16 Oct
5.0 out of 5 average rating, 420 reviews
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Chalet in Prattsville
NEW HOT TUB! Game Room • Firepit • Near Windham
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.76 out of 5 average rating, 42 reviews
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Home in Prattsville
Hot Tub • Sauna • Mtn View • Firepit • Home Office
3 bedrooms, 3 beds, 2 bathrooms
5–11 Oct
5.0 out of 5 average rating, 33 reviews
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Home in Jewett
Hot Tub | Sauna | Mountain Views | Fire Pit
4 bedrooms, 5 beds, 3.5 bathrooms
8–13 Nov
4.99 out of 5 average rating, 84 reviews
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Top guest favourite
Home in Windham
Modern Forest Retreat with Hot Tub and Sauna
4 bedrooms, 8 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 18 reviews
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Home in Windham
Windham Mountain Escape, Private 5 bed/4 bath home
5 bedrooms, 8 beds, 4 bathrooms
18–23 Sept
5.0 out of 5 average rating, 23 reviews
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Top guest favourite
Cabin in Jewett
Catskills Mountain Retreat: Luxury Meets Serenity
4 bedrooms, 4 beds, 3 bathrooms
18–23 Oct
5.0 out of 5 average rating, 19 reviews
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Top guest favourite
Home in Prattsville
Secluded Modern Mountain Home
4 bedrooms, 5 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 22 reviews
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Top guest favourite
Home in Prattsville
Modern Mountain Home - Near Windham & Hunter ski!
3 bedrooms, 3 beds, 2 bathrooms
2–7 Nov
5.0 out of 5 average rating, 39 reviews
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Top guest favourite
Home in Jewett
Mountain house w/ Scandinavian BBQ hut Spa & more!
3 bedrooms, 4 beds, 3 bathrooms
27 Sept – 2 Oct
4.93 out of 5 average rating, 230 reviews
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Top guest favourite
Home in Lexington
Valley View Chalet: AC, Hot Tub, Firepit, Games
3 bedrooms, 6 beds, 3 bathrooms
6–11 Dec
4.99 out of 5 average rating, 171 reviews