Pittsfield Cottages

Located in Cummington, this cottage is in a rural location, a 1-minute drive from Westfield River and 8 minutes from Chesterfield Gorge Reservation.

Located in Great Barrington, this cottage is on a lake, within a 5-minute drive of Lake Buel and Les Trois Emme Winery.

Located in Valatie, this cottage is on a lake, a 1-minute drive from Kinderhook Lake and 7 minutes from Valatie Free Library.

With a stay at this cottage in Great Barrington, you'll be steps from Lake Buel and a 4-minute drive from Les Trois Emme Winery.

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.

With a stay at this cottage in Charlemont, you'll be within a 15-minute drive of Deerfield River and Zoar Outdoor/Deerfield Valley Canopy Tours.

Located in Canaan, this cottage is on the waterfront, a 3-minute drive from Queechy Lake and 7 minutes from Furnace Brook Winery at Hilltop Orchards.

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.

With a stay at this cottage in Windsor, you'll be 8.1 mi (13 km) from Susan B. Anthony Birthplace Museum and 8.2 mi (13.2 km) from Tannery Falls.

Located in Great Barrington, this cottage is within a 10-minute drive of Art et Industrie and Housatonic River.

Located in Nassau, this cottage is on the waterfront, within a 15-minute drive of Berkshire Retreat Center and Kinderhook Lake.

With a stay at Berkshires farm, 30+ guests, 50 acres in New Lebanon, you'll be within a 5-minute drive of New Lebanon Library and Shatford Memorial Park.