Williamstown Cottages

Name: Spacious Historic Home in the Berkshires!
Address: Pittsfield

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Cottages in Williamstown

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 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.

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.

Welcome to the Red Bridge Cottage!

Located in Valatie, this cottage is in a rural location, within a 10-minute drive of Shaker Museum and Library and Valatie Free Library.

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.

Cross Country Ski? Downhill? Prospect and Mt Snow. Winter wonderland book now.

With a stay at this cottage in Bennington, you'll be on the waterfront, just steps from Green Mountain National Forest and a 2-minute drive from Prospect Mountain Nordic Ski Center.

Perfect for a peaceful get away in clean fresh Vermont air!

A stay at this cottage places you in the heart of Bennington, steps from Green Mountain National Forest and a 2-minute drive from Prospect Mountain Nordic Ski Center.

Lake life at Woodford Cottage

With a stay at this cottage in Bennington, you'll be on a river, just steps from Green Mountain National Forest and a 3-minute drive from Prospect Mountain Nordic Ski Center.

Morgan House Ski Lodge 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.

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.

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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.