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Search results; Over 1,000 homes in Windham

Guest favourite
Chalet in Windham
Secluded Fernwood Chalet, Hot Tub, & Sauna House
4 bedrooms, 5 beds, 2 private bathrooms
20–25 Sept
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4.94 out of 5 average rating, 119 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
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
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
Chalet in Windham
Windham Peak Chalet
3 bedrooms, 5 beds, 2.5 bathrooms
13–18 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
Guest favourite
Home in Windham
The Mad Brook House | Walk to Main St, Windham
2 bedrooms, 3 beds, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Windham
Small house, Windham, NY
2 bedrooms, 3 beds, 1 bathroom
11–16 Sept
4.97 out of 5 average rating, 237 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
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
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
Apartment in Windham
Hideaway Windham/Hunter Fireplace, Snow & Skiing
1 bedroom, 1 sofa bed, 1 bathroom
4–9 Oct
4.9 out of 5 average rating, 256 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
Home in Windham
Modern Cozy Townhome in Windham
2 bedrooms, 3 beds, 2.5 bathrooms
23–28 Sept
5.0 out of 5 average rating, 5 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
Guest favourite
Home in Hensonville
Spacious Townhome for an Upstate getaway!
2 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Townhouse in Windham
First Floor Condo with full kitchen.
2 beds, 1 bathroom
21–26 Sept
4.99 out of 5 average rating, 77 reviews
Guest favourite
Home in Windham
Comfy-Cozy Quads Hideaway
2 bedrooms, 5 beds, 2 bathrooms
5–10 Oct
4.87 out of 5 average rating, 15 reviews