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Search results; Over 1,000 homes in Windham

Guest favourite
Guest house in Windham
Little Bear’s Cottage Great location, cozy & cute
2 bedrooms, 3 beds, 1 private bathroom
20–25 Sept
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4.97 out of 5 average rating, 122 reviews
Top guest favourite
Chalet in Windham
Stargazing Dome|Sauna|Firepit|HotTub|Pet Frndly
5 bedrooms, 9 beds, 4.5 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 99 reviews
Home in Windham
Renovated Mountain House - Barrel Sauna & Fire Pit
4 bedrooms, 5 beds, 2.5 bathrooms
18–23 Oct
New place to stay
Top guest favourite
Cabin in Windham
5 Min to Skiing | Hot Tub | Fire Pit | Pool Table
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
4.98 out of 5 average rating, 197 reviews
Top guest favourite
Cabin in Windham
Aframe Escape | Hot tub | Movie Room | Karaoke
3 bedrooms, 4 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 59 reviews
Home in Windham
Luxury Windham Retreat | Hot tub + Speakeasy
5 bedrooms, 8 beds, 5.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Chalet in Windham
Gorgeous Lodge | Mt View, HotTub, Firepit, Game Rm
4 bedrooms, 8 beds, 3.5 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 184 reviews
Luxe
Cabin in Windham
NEW Modern Cabin 8 mins from Skiing-Hot Tub & Gym
5 bedrooms, 8 beds, 4 bathrooms
15–20 Sept
5.0 out of 5 average rating, 45 reviews
Top guest favourite
Home in Windham
EAT, DRINK, PLAY ... and Relax in Windham
5 bedrooms, 8 beds, 3 bathrooms
15–20 Sept
4.95 out of 5 average rating, 62 reviews
Top guest favourite
Home in Windham
Hyttå|Cozy Nordic Retreat|Hot Tub|Clubhouse|Wifi
4 bedrooms, 6 beds, 2 bathrooms
20–25 Sept
4.96 out of 5 average rating, 25 reviews
Top guest favourite
Chalet in Windham
Luxe Lodge w/ Mt View | Hot Tub, Fire Pit, Game Rm
5 bedrooms, 9 beds, 4.5 bathrooms
20–25 Sept
4.98 out of 5 average rating, 174 reviews
Top guest favourite
Home in Windham
Windham Vacation with Heated Pool, Hot Tub & Sauna
5 bedrooms, 5 beds, 4.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 48 reviews
Top guest favourite
Home in Windham
River & Golf Mountain Retreat
4 bedrooms, 5 beds, 4 bathrooms
15–20 Sept
5.0 out of 5 average rating, 89 reviews
Top guest favourite
Cabin in Windham
Windham Cabin - On 80 Acres - 4 Mi to Ski Resort
6 bedrooms, 13 beds, 6.5 bathrooms
22–27 Sept
4.94 out of 5 average rating, 36 reviews
Top guest favourite
Cabin in Windham
Catskills Designer Retreat near Hiking + Swimming
4 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
4.97 out of 5 average rating, 142 reviews
Chalet in Windham
Windham Peak Chalet
3 bedrooms, 5 beds, 2.5 bathrooms
16–21 Sept
New place to stay
Top guest favourite
Home in Windham
Family-ready retreat, games and BBQ
3 bedrooms, 6 beds, 2.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 55 reviews
Top guest favourite
Chalet in Windham
Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven
4 bedrooms, 10 beds, 4 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 27 reviews
Top guest favourite
Chalet in Windham
Velvet Timber Haus | HotTub, Sauna, Firepit, Games
7 bedrooms, 11 beds, 3.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 18 reviews