Book Guest Houses in Chatham, NY
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Top Guest Houses in Chatham
The Central Downtown Inn & Suites
20 W Housatonic St. Pittsfield MA
$85 nightly
The price is $95 total per night
$95 total
Dec 11 - Dec 12
Total with taxes and fees
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, express check-in, and express check-out are also on offer.
Pet friendly
Parking included
Berkshire Village Carriage House - Super Private!!
Lanesborough MA
$189 nightly
The price is $211 total per night
$211 total
Dec 11 - Dec 12
Total with taxes and fees
This guesthouse includes a garden and barbecue grills.
Free WiFi
Air conditioning
The Dewey
7 Hubbard Street Lenox MA
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.
Parking included
Free WiFi
Hudson valley and The Berkshires Cottage
Hillsdale NY
$297 nightly
The price is $301 total per night
$301 total
Dec 15 - Dec 16
Total with taxes and fees
This guesthouse includes a garden and laundry facilities.
Pet friendly
Free WiFi
LEEDS A GREAT ESCAPE
Leeds NY
This guesthouse includes a garden and barbecue grills.
Air conditioning
Parking available
Renovated Private Guest House by Evergreen Home
Great Barrington MA
This guesthouse features a garden, laundry facilities, and barbecue grills.
Pet friendly
Free WiFi
Jacob's Tanglewood Ranch
560 Stockbridge Rd Lee MA
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a lobby fireplace, and a communal living room are also on offer.
Pet friendly
Parking included
1805 House Bed and Breakfast
775 Snydertown Road Craryville NY
This guesthouse features free self parking and a terrace. Enjoy the free continental breakfast each morning. A garden and a picnic area are also provided.
Breakfast included
Parking included
Chestnut Lodge
75 Chestnut Street Lee MA
A hot tub is featured at this guesthouse, along with free self parking. WiFi in public areas is free. A terrace and a picnic area are also provided.
Hot Tub
Parking included
Cliffwood Cottage by Evergreen Home
Lenox MA
This guesthouse features laundry facilities.
Free WiFi
Air conditioning
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.
Top hotels in Chatham
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$108 nightly
The price is $120 total per night from Jan 8 to Jan 9
$120 total
Jan 8 - Jan 9, 2026
Total with taxes and fees
9/10 Wonderful! (778 reviews)
Chatham Guest Houses essential information
Accommodation | 11 Guest Houses |
|---|---|
Lowest Price | $84 |
Highest Price | $301 |
Popular accommodation | The Central Downtown Inn & Suites, Berkshire Village Carriage House - Super Private!!, The Dewey, Hudson valley and The Berkshires Cottage, LEEDS A GREAT ESCAPE, Renovated Private Guest House by Evergreen Home, Jacob's Tanglewood Ranch, 1805 House Bed and Breakfast , Chestnut Lodge, Cliffwood Cottage by Evergreen Home, Vanderbilt Lakeside |
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