Cheshire Cottages
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Cottages in Cheshire
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.
Kitchen
Free WiFi
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
Cozy cottage with pool, walking distance to lake
When you stay at this cottage in Averill Park, you'll be on a lake and 14 minutes by car from Pineridge Cross Country Ski Center.
Pool
Kitchen
Morgan House on Crooked Lake
A stay at this cottage places you in the heart of Averill Park, and within a 15-minute drive of Pineridge Cross Country Ski Center.
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.
Kitchen
Pet friendly
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.
Kitchen
Pet friendly
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.
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.
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.
Cheshire Cottages essential information
Accommodation | 56 Cottages |
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Lowest Price | |
Highest Price | |
Popular accommodation | Charming historic cottage on scenic road to Mt. Greylock, Cozy Berkshire cottage with fireplace., Cozy cottage with pool, walking distance to lake, Morgan House on Crooked Lake, 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, Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!, Picturesque Cottage with Sunroom on Ashmere Lake! |