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Search results; Over 1,000 homes in Windham

Top guest favourite
Chalet in Windham
Luxe Lodge w/ Mt View | Hot Tub, Fire Pit, Game Rm
5 bedrooms, 9 beds, 4.5 private bathrooms
20–25 Aug
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4.98 out of 5 average rating, 173 reviews
Top guest favourite
Chalet in Windham
Stargazing Dome|Sauna|Firepit|HotTub|Pet Frndly
5 bedrooms, 9 beds, 4.5 bathrooms
7–12 Sept
4.98 out of 5 average rating, 93 reviews
Top guest favourite
Cabin in Windham
5 Min to Skiing | Hot Tub | Fire Pit | Pool Table
3 bedrooms, 3 beds, 2 bathrooms
25–30 Aug
4.98 out of 5 average rating, 191 reviews
Top guest favourite
Cabin in Windham
Cozy Creekside Cabin | 5 Mins to Windham Mt!
3 bedrooms, 4 beds, 1 bathroom
7–12 Sept
4.95 out of 5 average rating, 224 reviews
Top guest favourite
Home in Windham
Modern Forest Retreat with Hot Tub and Sauna
4 bedrooms, 8 beds, 3 bathrooms
23–28 Aug
5.0 out of 5 average rating, 16 reviews
Home in Windham
Hot Tub · Fire pit · Pond · Minutes to Windham
4 bedrooms, 7 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Chalet in Windham
Gorgeous Lodge | Mt View, HotTub, Firepit, Game Rm
4 bedrooms, 8 beds, 3.5 bathrooms
30 Aug – 4 Sept
4.97 out of 5 average rating, 181 reviews
Top guest favourite
Townhouse in Windham
First Floor Condo with full kitchen.
2 beds, 1 bathroom
17–22 Aug
4.99 out of 5 average rating, 74 reviews
Top guest favourite
Cabin in Windham
Aframe Escape | Hot tub | Movie Room | Karaoke
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 48 reviews
Top guest favourite
Cabin in Windham
Catskills Designer Retreat near Hiking + Swimming
4 bedrooms, 4 beds, 2 bathrooms
17–22 Aug
4.97 out of 5 average rating, 139 reviews
Guest favourite
Townhouse in Windham
Secluded and Scenic Large Townhouse
3 bedrooms, 7 beds, 2.5 bathrooms
17–22 Aug
4.94 out of 5 average rating, 52 reviews
Top guest favourite
Home in East Jewett
Creekside Couple's Escape w/ Hot Tub Sauna & More!
1 bedroom, 2 beds, 1.5 bathrooms
28 Nov – 3 Dec
5.0 out of 5 average rating, 23 reviews
Guest favourite
Home in Windham
5 Min to Skiing | Hot Tub | Fire Pit | Pool Table
6 bedrooms, 6 beds, 3 bathrooms
17–22 Aug
4.97 out of 5 average rating, 31 reviews
Guest favourite
Home in Hensonville
Spacious Townhome for an Upstate getaway!
2 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Chalet in Windham
Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven
4 bedrooms, 10 beds, 4 bathrooms
18–23 Aug
4.96 out of 5 average rating, 26 reviews
Home in Windham
Luxury Windham Retreat | Hot tub + Speakeasy
5 bedrooms, 8 beds, 5.5 bathrooms
24–29 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Jewett
Mountain house w/ Scandinavian BBQ hut Spa & more!
3 bedrooms, 4 beds, 3 bathrooms
30 Aug – 4 Sept
4.94 out of 5 average rating, 226 reviews
Top guest favourite
Home in Windham
Family-ready retreat, games and BBQ
3 bedrooms, 6 beds, 2.5 bathrooms
18–23 Aug
5.0 out of 5 average rating, 54 reviews
Top guest favourite
Chalet in Town of Gilboa
Luxurious Chalet w/ Incredible Views on 20+ Acres
3 bedrooms, 4 beds, 2 bathrooms
25–30 Aug
4.98 out of 5 average rating, 207 reviews