Chesterfield Cottages
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Cottages in Chesterfield
Private Island - Largest Fresh Water Reservoir in Mass....
With a stay at this cottage in Otis, you'll be on the waterfront, just steps from Otis Reservoir and a 4-minute drive from Larkum Pond.
Kitchen
Pet friendly
East Otis Vacation Rental w/ Private Deck & BBQ!
With a stay at this cottage in Otis, you'll be steps from Otis Reservoir and a 3-minute drive from Larkum Pond.
Kitchen
Outdoor Space
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
Massachusetts Vacation Rental w/ Deck
With a stay at this cottage in Easthampton, you'll be within a 10-minute drive of Smith College and Academy of Music Theater.
Kitchen
Pet friendly
Lake Views & Dock Access - Pittsfield Cottage!
Located in Pittsfield, this cottage is on the waterfront, within a 10-minute drive of Pittsfield Dog Park and Crane Museum of Papermaking.
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.
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
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
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.
Chesterfield Cottages essential information
Accommodation | 40 Cottages |
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Lowest Price | |
Highest Price | |
Popular accommodation | Private Island - Largest Fresh Water Reservoir in Mass...., East Otis Vacation Rental w/ Private Deck & BBQ!, Charming historic cottage on scenic road to Mt. Greylock, Massachusetts Vacation Rental w/ Deck, Lake Views & Dock Access - Pittsfield 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, Picturesque Cottage with Sunroom on Ashmere Lake!, Historic Huntington Home - Walk to Westfield River, Private Lake Cottage on 3 acres w/350 sq. ft. deck |