Chatham Guest Houses

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Guest Houses in Chatham

The Central Downtown Inn & Suites

20 W Housatonic St. Pittsfield MA

$99 nightly

$111 total

Mar 11 - Mar 12

Total with taxes and fees

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

Hudson valley and The Berkshires Cottage

Hillsdale NY

$314 nightly

$319 total

Mar 16 - Mar 17

Total with taxes and fees

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

Free WiFi

The Dewey

7 Hubbard Street Lenox MA

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

Parking included

Free WiFi

LEEDS A GREAT ESCAPE

Leeds NY

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.

Air conditioning

Parking available

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.

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 Housatonic River.

Hot Tub

Parking included

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 Columbia-Greene Hospital Foundation.

Breakfast included

Parking included

Cliffwood Cottage by Evergreen Home

Lenox MA

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

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.

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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.