Stockbridge 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 this guesthouse in Sandisfield, you'll be in the mountains and 7 minutes by car from Cookson State Forest.

With a stay at this cottage 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 Housatonic River and Lake Mansfield Park.

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 Jacob's Tanglewood Ranch in Lee, you'll be within a 5-minute drive of Greenock Country Club and Berkshire Theatre Festival.

With a stay at Chestnut Lodge in Lee, you'll be within a 5-minute drive of October Mountain State Forest and Housatonic River.

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

Located in Becket, Guest House Sanctuary by Evergreen Home is a 5-minute drive from Pyramid Lake and 5 minutes from Jacob's Pillow.