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Search results; Over 1,000 homes in Windham

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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, 123 reviews
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Home in Windham
Renovated Mountain House - Barrel Sauna & Fire Pit
4 bedrooms, 5 beds
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
27 Sept – 2 Oct
4.98 out of 5 average rating, 100 reviews
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Top guest favourite
Home in Windham
Luxury Windham Retreat | Hot tub + Speakeasy
5 bedrooms, 8 beds
21–26 Sept
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Cabin in Windham
Aframe Escape | Hot tub | Movie Room | Karaoke
3 bedrooms, 4 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 60 reviews
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Top guest favourite
Chalet in Windham
Gorgeous Lodge | Mt View, HotTub, Firepit, Game Rm
4 bedrooms, 8 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 184 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
27 Sept – 2 Oct
4.98 out of 5 average rating, 174 reviews
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Guest favourite
Home in Windham
Comfy-Cozy Quads Hideaway
2 bedrooms, 5 beds
5–10 Oct
4.87 out of 5 average rating, 15 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
20–25 Sept
4.98 out of 5 average rating, 197 reviews
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Top guest favourite
Townhouse in Windham
Windham Mountain Village 2 bedroom townhouse
3 bedrooms, 7 beds
4–9 Oct
4.91 out of 5 average rating, 138 reviews
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Guest favourite
Home in Windham
Pool |MTNView| HotTub |Sauna| Games|Movie| Firepit
6 bedrooms, 9 beds
12–17 Oct
4.97 out of 5 average rating, 37 reviews
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Chalet in Windham
Windham Peak Chalet
3 bedrooms, 5 beds
21–26 Sept
New place to stay
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Top guest favourite
Home in Windham
Small house, Windham, NY
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 238 reviews
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Luxe
Cabin in Windham
NEW Modern Cabin 8 mins from Skiing-Hot Tub & Gym
5 bedrooms, 8 beds
20–25 Sept
5.0 out of 5 average rating, 45 reviews
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Guest favourite
Townhouse in Windham
Mill House 2 | 3BD + 3.5 Bath Catskills Retreat
3 bedrooms, 5 beds
20–25 Sept
4.92 out of 5 average rating, 78 reviews
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Guest favourite
Townhouse in Windham
Cheerful and Cozy 2 bedroom home in Windham
2 bedrooms, 4 beds
20–25 Sept
4.97 out of 5 average rating, 62 reviews
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Guest favourite
Home in Windham
Windham Villa | 6BDRM, Pool, Hot Tub & Movie Room
6 bedrooms, 8 beds
20–25 Sept
4.95 out of 5 average rating, 109 reviews
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Guest favourite
Home in Hensonville
Spacious Townhome for an Upstate getaway!
2 bedrooms, 4 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 13 reviews
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Guest favourite
Cabin in Windham
The Windham A
3 bedrooms
20–25 Sept
4.95 out of 5 average rating, 40 reviews