Old Chatham Guest Houses

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Guest Houses in Old Chatham

The Central Downtown Inn & Suites

20 W Housatonic St., Pittsfield, MA

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

Pet friendly

Parking included

Hudson valley and The Berkshires Cottage

$88

per night

May 29 - May 30

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.

Pet friendly

Air conditioning

Suite East Side

With a stay at this guesthouse in Troy, you'll be within a 15-minute drive of Rensselaer Polytechnic Institute and MVP Arena.

Renovated Private Guest House by Evergreen Home

With a stay at this guesthouse in Great Barrington, you'll be within a 10-minute drive of Housatonic River and Lake Mansfield Park.

Pet friendly

Free WiFi

1805 House Bed and Breakfast

775 Snydertown Road, Craryville, NY

Located in Craryville, 1805 House Bed and Breakfast is in a rural location, within a 15-minute drive of Claverack Library and Lake Taghkanic State Park.

Jacob's Tanglewood Ranch

560 Stockbridge Rd, Lee, MA

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.

Pet friendly

Parking included

Chestnut Lodge

75 Chestnut Street, Lee, MA

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

Vanderbilt Lakeside

161 Main St, Philmont, NY

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

Breakfast included

Parking included

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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.