Pittsfield Cottages

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

When you stay at this cottage in Otis, you'll be on a lake, within a 5-minute drive of County Beach and Otis Ridge.

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

Located in Lanesborough, this cottage is in the mountains, a 3-minute drive from Mount Greylock State Reservation and 5 minutes from Mount Greylock State Reservation Visitor Center.

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.

Located in Averill Park, this cottage is on a lake, within a 15-minute drive of Sand Lake Center for the Arts and Berkshire Retreat Center.

Located in Becket, this cottage is a 4-minute drive from Iroquis Waterfront and 8 minutes from Becket Quarry.

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.

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.

When you stay at this cottage in Monterey, you'll be within a 10-minute drive of Bidwell House Museum and Dry Hill.

When you stay at this cottage in West Stockbridge, you'll be on a lake, within a 10-minute drive of Tanglewood Music Center and National Shrine of the Divine Mercy.