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Cottages in Windham County
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Our top choices for Windham County cottages

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendlyWilmington
8.6 out of 10, Excellent, (66 reviews)

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
The Cairn, 1840s Cozy Stone Cottage, Pet FriendlyChester
10.0 out of 10, Exceptional, (20 reviews)

Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!Whitingham

Rare new Home on Lake Whitingham. Semi-priv beach
Rare new Home on Lake Whitingham. Semi-priv beachWilmington
10.0 out of 10, Exceptional, (6 reviews)

10 Mi to Mt Snow! Grand Estate Built to Entertain
10 Mi to Mt Snow! Grand Estate Built to EntertainWilmington
10.0 out of 10, Exceptional, (1 review)

Hiking Trails On-site: Cozy Falls Brook Cabin
Hiking Trails On-site: Cozy Falls Brook CabinBrattleboro
10.0 out of 10, Exceptional, (2 reviews)

Cottage-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK
Cottage-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OKJamaica
10.0 out of 10, Exceptional, (3 reviews)

Charming Putney Home: Porch, Grill & Hiking Trails
Charming Putney Home: Porch, Grill & Hiking TrailsPutney
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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Top Windham County Hotel Reviews

The Covered Bridge Inn
10/10 Excellent
















































































