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Compare 49 Cottages in Winchester with updated reviews, rates, and availability.

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-friendly
8.8 out of 10, Excellent, (47)

Waterfront Cottage on Scenic Sportsman Pond
Waterfront Cottage on Scenic Sportsman Pond
9.6 out of 10, Exceptional, (41)

Cottage on Partridge Pond
Cottage on Partridge Pond
10.0 out of 10, Exceptional, (19)

Vacationer's oasis on the waterfront of picturesque Pearly Pond.
Vacationer's oasis on the waterfront of picturesque Pearly Pond.
10.0 out of 10, Exceptional, (29)

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
10.0 out of 10, Exceptional, (7)
The price is AED 814
AED 999 total
includes taxes & fees
8 Jun - 9 Jun

Finnish Cabin with Sauna on Lake Monomonac
Finnish Cabin with Sauna on Lake Monomonac
10.0 out of 10, Exceptional, (10)
The price is AED 823
AED 1,232 total
includes taxes & fees
9 Jun - 10 Jun

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
10.0 out of 10, Exceptional, (17)

Beautiful Waterfront Cottage With a HOT TUB For Your Family Getaway!
Beautiful Waterfront Cottage With a HOT TUB For Your Family Getaway!
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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Recent reviews of Winchester hotels
Recent reviews of Winchester hotels

Hampton Inn & Suites Greenfield
5/5 Excellent
"Staff were terrific. Property is in good condition while renovation is taking place.
Pool is very nice."
A verified traveler stayed at Hampton Inn & Suites Greenfield
Posted 23 hours ago