Windsor Cottages
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Cottages in Windsor
Charming historic cottage on scenic road to Mt. Greylock
With a stay at this cottage in Lanesborough, you'll be in the mountains, within a 10-minute drive of Jiminy Peak Mountain Resort and Mount Greylock State Reservation.
Cozy Berkshire cottage with fireplace.
Located in Pittsfield, this cottage is in the mountains, within a 5-minute drive of Guido's Marketplace and Berkshire Museum.
Kitchen
Washer
Beachwood Cottage
Located in West Stockbridge, this cottage is on a lake, a 5-minute drive from Frelinghuysen Morris House and Studio and 6 minutes from Tanglewood Music Center.
Kitchen
Washer
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
With a stay at this cottage in Charlemont, you'll be within a 10-minute drive of Deerfield River and Mohawk Trail State Forest.
Spacious Historic Home in the Berkshires!
With a stay at this cottage in Pittsfield, you'll be within a 10-minute walk of Colonial Theater and Berkshire Athenaeum.
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
With a stay at this cottage in Williamsburg, you'll be within a 10-minute drive of Silvio O. Conte National Fish and Wildlife Refuge and Three Sisters Sanctuary.
Kitchen
Pet friendly
Charlemont Retreat on Chickley River w/ EV Charger
Located in Charlemont, this cottage is within a 15-minute drive of Mohawk Trail State Forest and Zoar Outdoor/Deerfield Valley Canopy Tours.
Kitchen
Pet friendly
Cottage in the Clouds With Mountain Views
Located in New Lebanon, this cottage is on a lake, within a 10-minute drive of Shatford Memorial Park and New Lebanon Library.
Kitchen
Pet friendly
Picturesque Cottage with Sunroom on Ashmere Lake!
Located in Hinsdale, this cottage is on the waterfront, within a 15-minute drive of Bas Ridge Golf Course and Crane Museum of Papermaking.
Kitchen
Washer
Stockbridge Home: Walk to Town Beach!
With a stay at this cottage in Stockbridge, you'll be within a 5-minute drive of Frelinghuysen Morris House and Studio and Tanglewood Music Center.
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.
Windsor Cottages essential information
Accommodation | 51 Cottages |
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Highest Price | |
Popular accommodation | Charming historic cottage on scenic road to Mt. Greylock, Cozy Berkshire cottage with fireplace., Beachwood Cottage, Hawley Home w/ Deck: 4 Mi to Berkshire East Resort, Spacious Historic Home in the Berkshires!, Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!, Charlemont Retreat on Chickley River w/ EV Charger, Cottage in the Clouds With Mountain Views, Picturesque Cottage with Sunroom on Ashmere Lake!, Stockbridge Home: Walk to Town Beach!, Historic Huntington Home - Walk to Westfield River, Private Lake Cottage on 3 acres w/350 sq. ft. deck |