Chatham Guest Houses

Located in Pittsfield, The Central Downtown Inn & Suites is a 1-minute drive from Berkshire Museum and 7 minutes from Bousquet Ski Area.

When you stay at Hideaway Inn Lenox in Lenox, you'll be near ski lifts, within a 5-minute drive of Shakespeare and Company and Tanglewood Music Center.

Located in Lanesborough, this guesthouse is in the mountains, a 4-minute drive from Cheshire Reservoir and 6 minutes from Pontoosuc Lake.

Located in Catskill, this guesthouse is in a rural location, a 5-minute drive from Catskill Golf Club and 5 minutes from Thomas Cole National Historic Site.

With a stay at The Dewey in Lenox, you'll be in the suburbs, within a 5-minute drive of Tanglewood Music Center and Lenox Library.

With a stay at this guesthouse in Hillsdale, you'll be within a 15-minute drive of W.E.B. Du Bois Boyhood Homesite and Hillsdale Town Hall.

Located in Great Barrington, this guesthouse is in a rural location, within a 10-minute drive of Monument Mountain and Housatonic River.

With a stay at this guesthouse, you'll be centrally located in Lenox, within a 5-minute drive of Tanglewood Music Center and Lenox Library.

Located in Craryville, 1805 House Bed and Breakfast is in a rural location, within a 15-minute drive of Claverack Library and Columbia-Greene Hospital Foundation.

With a stay at Chestnut Lodge in Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Housatonic River.

With a stay at Jacob's Tanglewood Ranch in Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Greenock Country Club.

Located in Philmont, Vanderbilt Lakeside is on a lake, within a 15-minute drive of High Falls Trail and Claverack Library.