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Compare 50 Cottages in Windsor with updated reviews, rates, and availability.
Charming historic cottage on scenic road to Mt. Greylock
Charming historic cottage on scenic road to Mt. Greylock
10.0 out of 10, Exceptional, (101)
Cozy Berkshire cottage with fireplace.
Cozy Berkshire cottage with fireplace.
10.0 out of 10, Exceptional, (20)
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
6.0 out of 10, (1)
Charlemont Retreat on Chickley River w/ EV Charger
Charlemont Retreat on Chickley River w/ EV Charger
10.0 out of 10, Exceptional, (1)
Cottage in the Clouds With Mountain Views
Cottage in the Clouds With Mountain Views
9.4 out of 10, Exceptional, (3)
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 Windsor
Vacation Village in the Berkshires
Vacation Village in the Berkshires
8.6 out of 10, Excellent, (1713)
The price is SAR 633
SAR 732 total
includes taxes & fees
23 Sep - 24 Sep
The price is SAR 559
SAR 613 total
includes taxes & fees
14 Oct - 15 Oct
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 Windsor hotels
Recent reviews of Windsor hotels
5/5 Excellent
"This is a family owned motel and they made us feel like family in that they took great care of us. The family went the extra mile and helped to recover from our section hike. I would gladly stay here again. We stopped at the Trail house kitchen and bar on the way off the Appalachian trail and had the excellent Berkshire burger. A great meal and a great stay who could ask for more."
A verified traveler stayed at Willows Motel Williamstown
Posted 10 hours ago
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