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Search results; Over 1,000 homes in Windham

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Guest favourite
Apartment in Windham
Luxury 5 * Ski-in Ski-out @ Whisper Creek
3 bedrooms, 6 beds, 3 private bathrooms
17–22 Sept
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5.0 out of 5 average rating, 11 reviews
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Cabin in Durham
Spectacular Windham Chalet with Sauna & Hot Tub
4 bedrooms, 7 beds, 3 bathrooms
18–23 Sept
New place to stay
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Home in Windham
Renovated Mountain House - Barrel Sauna & Fire Pit
4 bedrooms, 5 beds, 2.5 bathrooms
26–31 Oct
New place to stay
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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, 100 reviews
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Home in Windham
Luxury Windham Retreat | Hot tub + Speakeasy
5 bedrooms, 8 beds, 5.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 5 reviews
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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
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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
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Chalet in Windham
Windham Peak Chalet
3 bedrooms, 5 beds, 2.5 bathrooms
18–23 Sept
New place to stay
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Top guest favourite
Home in Windham
Small house, Windham, NY
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 237 reviews
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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
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Home in Windham
Cascade House Alpine Retreat
4 bedrooms, 5 beds, 2.5 bathrooms
18–23 Sept
New place to stay
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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, 60 reviews
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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
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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
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Guest favourite
Chalet in Windham
A Windham Chalet for All Seasons
4 bedrooms, 9 beds, 2 bathrooms
25–30 Oct
4.96 out of 5 average rating, 141 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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Superhost
Home in Windham
Le Mont Bleu- Pickleball, Hot tub, Sauna, Game Rm
5 bedrooms, 9 beds, 3.5 bathrooms
21–26 Sept
New place to stay
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Top guest favourite
Cabin in Windham
CozyCatskillChalet w/ Hot Tub (Catskill Mountains)
2 bedrooms, 3 queen beds, 1 bathroom
17–22 Sept
4.95 out of 5 average rating, 515 reviews
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Guest favourite
Apartment in Windham
Slope Side Luxe | Views, Decks, Walk to Mtn & Town
5 bedrooms, 8 beds, 5.5 bathrooms
17–22 Sept
4.98 out of 5 average rating, 45 reviews