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Search results; Over 1,000 homes in Ashland

Top guest favourite
Cabin in Town of Ashland
Luxury Cabin Retreat - 7 Mins to Windham
3 bedrooms, 8 beds, 2 private bathrooms
14–19 Sept
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5.0 out of 5 average rating, 32 reviews
Top guest favourite
Cabin in Windham
Cozy Creekside Cabin | 5 Mins to Windham Mt!
3 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 226 reviews
Guest favourite
Cabin in Windham
Dream cabin
5 bedrooms, 7 beds, 3 bathrooms
19–24 Oct
4.89 out of 5 average rating, 61 reviews
Top guest favourite
Home in Windham
Private cabin in the Catskills
2 bedrooms, 2 queen beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 419 reviews
Guest favourite
Home in Windham
Creekside Lodge | Windham | A/C | Sleeps 12
4 bedrooms, 8 beds, 3 bathrooms
28 Sept – 3 Oct
4.93 out of 5 average rating, 72 reviews
Top guest favourite
Home in Windham
Entire Magda Cabin XL! Sauna! Hot Tub!
7 bedrooms, 13 beds, 5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Prattsville
Hot Tub • Sauna • Mtn View • Firepit • Home Office
3 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Home in Prattsville
Modern Mountain Home - Near Windham & Hunter ski!
3 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 39 reviews
Top guest favourite
Cabin in Windham
Catskills Designer Retreat near Hiking + Swimming
4 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
4.97 out of 5 average rating, 141 reviews
Top guest favourite
Home in Prattsville
Our Ski House
4 bedrooms, 6 queen beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Home in Windham
Modern Forest Retreat with Hot Tub and Sauna
4 bedrooms, 8 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 16 reviews
Home in Windham
Windham Mountain Escape, Private 5 bed/4 bath home
5 bedrooms, 8 beds, 4 bathrooms
13–18 Sept
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Home in Prattsville
10 min to Windham! 20 min to Hunter! EV charger!
3 bedrooms, 8 beds, 3 bathrooms
12–17 Sept
5.0 out of 5 average rating, 44 reviews
Top guest favourite
Home in Prattsville
Gem w Hot tub/Pond/ 9 min to Ski
4 bedrooms, 6 beds, 4 bathrooms
14–19 Sept
5.0 out of 5 average rating, 10 reviews
Chalet in Prattsville
NEW HOT TUB! Game Room • Firepit • Near Windham
4 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
4.76 out of 5 average rating, 42 reviews
Chalet in Windham
Windham Peak Chalet
3 bedrooms, 5 beds, 2.5 bathrooms
13–18 Sept
New place to stay
Top guest favourite
Home in Prattsville
Scandi A-Frame w/Hot Tub & Sauna
3 bedrooms, 6 beds, 2 bathrooms
27 Sept – 2 Oct
4.99 out of 5 average rating, 154 reviews
Top guest favourite
Cabin in Windham
Windham Cabin - On 80 Acres - 4 Mi to Ski Resort
6 bedrooms, 13 beds, 6.5 bathrooms
21–26 Sept
4.94 out of 5 average rating, 36 reviews
Top guest favourite
Chalet in Jewett
Luxe Party Retreat: Ski| Pool |Karaoke|Game| Movie
5 bedrooms, 6 queen beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 93 reviews