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Compare 187 Cottages in Windham with updated reviews, rates, and availability.

Streamside Cottage Half Mile to Town of Woodstock
Streamside Cottage Half Mile to Town of Woodstock
10.0 out of 10, Exceptional, (230)

ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi
10.0 out of 10, Exceptional, (77)

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
10.0 out of 10, Exceptional, (60)

Charming Cottage in Private Lake Community (Pet-Friendly!)
Charming Cottage in Private Lake Community (Pet-Friendly!)
9.8 out of 10, Exceptional, (27)

Private Home ~ All Yours ~ In town ~ fenced in yard ~ Hot Tub ~ Pets welcome!
Private Home ~ All Yours ~ In town ~ fenced in yard ~ Hot Tub ~ Pets welcome!
9.8 out of 10, Exceptional, (110)

Experience Peace in this Beautiful country cottage nestled beneath the mountains
Experience Peace in this Beautiful country cottage nestled beneath the mountains
10.0 out of 10, Exceptional, (4)

The Cabin at Chichester in the Catskills Mountains
The Cabin at Chichester in the Catskills Mountains
9.8 out of 10, Exceptional, (180)

Romantic cottage w/hot tub . Close to skiing and breweries . Pet friendly!
Romantic cottage w/hot tub . Close to skiing and breweries . Pet friendly!
10.0 out of 10, Exceptional, (13)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Windham

A'Neils Windham Ski Lodge & Family Retreat
A'Neils Windham Ski Lodge & Family Retreat
10.0 out of 10, Exceptional, (28)

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge
10.0 out of 10, Exceptional, (154)

Tuscan Year Round Beauty - Pickleball Court
Tuscan Year Round Beauty - Pickleball Court
10.0 out of 10, Exceptional, (98)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Recent reviews of Windham hotels
Recent reviews of Windham hotels

Woodstock Way Hotel
5/5 Excellent
Quiet solitude in the heart of Woodstock
"This hotel was an amazing stay for us with our young baby. The location is right in the middle of Woodstock's main Street right walking distance from everywhere, all the best restaurants etc. However it seems like a nice natural setting with a waterfall and nice seating next to it. The best perk was the unlimited free caffeine from the lobby receptionists who double as baristas! Wonderful service and stay all around. "
A verified traveler stayed at Woodstock Way Hotel
Posted 22 hours ago
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