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Search results; Over 1,000 homes in Windham

Holiday home in Windham
Luxurious 4 BR Condo at Windham Mountain Resort
4 bedrooms, 8 beds, 4 private bathrooms
11–16 Sept
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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
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, 57 reviews
Home in Windham
Cascade House Alpine Retreat
4 bedrooms, 5 beds, 2.5 bathrooms
11–16 Sept
New place to stay
Chalet in Windham
Windham Peak Chalet
3 bedrooms, 5 beds, 2.5 bathrooms
11–16 Sept
New place to stay
Home in Windham
Luxury Windham Retreat | Hot tub + Speakeasy
5 bedrooms, 8 beds, 5.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Cabin in Windham
5 Min to Skiing | Hot Tub | Fire Pit | Pool Table
3 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.98 out of 5 average rating, 196 reviews
Top guest favourite
Chalet in Windham
Velvet Timber Haus | HotTub, Sauna, Firepit, Games
7 bedrooms, 11 beds, 3.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Chalet in Windham
Gorgeous Lodge | Mt View, HotTub, Firepit, Game Rm
4 bedrooms, 8 beds, 3.5 bathrooms
12–17 Sept
4.97 out of 5 average rating, 183 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
12–17 Sept
4.98 out of 5 average rating, 174 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
Top guest favourite
Home in Windham
Small house, Windham, NY
2 bedrooms, 3 beds, 1 bathroom
10–15 Sept
4.97 out of 5 average rating, 237 reviews
Guest favourite
Townhouse in Windham
Cheerful and Cozy 2 bedroom home in Windham
2 bedrooms, 4 beds, 2 bathrooms
11–16 Sept
4.98 out of 5 average rating, 61 reviews
Top guest favourite
Cottage in Windham
Cozy Cottage Retreat Close to Main St/Windham Mtn
2 bedrooms, 2 king beds, 1 bathroom
12–17 Sept
4.99 out of 5 average rating, 70 reviews
Home in Windham
5 Min to Skiing | Hot Tub | Fire Pit | Pool Table
6 bedrooms, 6 beds, 3 bathrooms
13–18 Sept
4.91 out of 5 average rating, 32 reviews
Guest favourite
Townhouse in Windham
Mill House 2 | 3BD + 3.5 Bath Catskills Retreat
3 bedrooms, 5 beds, 3.5 bathrooms
14–19 Sept
4.92 out of 5 average rating, 78 reviews
Superhost
Home in Windham
“Ski/Hike/Mtn Bike out the door Trailside Chalet”
4 bedrooms, 8 beds, 3 bathrooms
10–15 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Windham
Pool |MTNView| HotTub |Sauna| Games|Movie| Firepit
6 bedrooms, 9 beds, 3 bathrooms
5–10 Oct
4.97 out of 5 average rating, 37 reviews
Luxe
Cabin in Windham
NEW Modern Cabin 8 mins from Skiing-Hot Tub & Gym
5 bedrooms, 8 beds, 4 bathrooms
10–15 Sept
5.0 out of 5 average rating, 44 reviews