Chatham Guest Houses

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Guest Houses in 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

LEEDS A GREAT ESCAPE

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

Hudson valley and The Berkshires Cottage

$296

includes taxes & fees

$296 per night

Jan 8 - Jan 9, 2025

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

Renovated Private Guest House by Evergreen Home

Located in Great Barrington, this guesthouse is in a rural location, 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 Columbia-Greene Hospital Foundation.

Breakfast included

Parking included

Jacob's Tanglewood Ranch

560 Stockbridge Rd, Lee, MA

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.

Pet friendly

Parking included

Chestnut Lodge

75 Chestnut Street, Lee, MA

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

Hot Tub

Parking included

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.