Book Guest Houses in Old Chatham, NY

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Top Guest Houses in Old Chatham

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St. Pittsfield MA
$94 nightly
The price is $105 total per night
$105 total
Jan 25 - Jan 26
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.
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough MA
$188 nightly
The price is $210 total per night
$210 total
Jan 13 - Jan 14
Total with taxes and fees
This guesthouse includes a garden and barbecue grills.
The Dewey

The Dewey

3.5 out of 5
7 Hubbard Street Lenox MA
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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.
Hudson valley and The Berkshires Cottage

Hudson valley and The Berkshires Cottage

Hillsdale NY
$341 nightly
The price is $346 total per night
$346 total
Jan 14 - Jan 15
Total with taxes and fees
A garden is available at this guesthouse.
Tranquil Retreat - Comfort and Convenience.

Tranquil Retreat - Comfort and Convenience.

Delmar NY
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This guesthouse features barbecue grills.
Renovated Private Guest House by Evergreen Home

Renovated Private Guest House by Evergreen Home

Great Barrington MA
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This guesthouse features a garden, laundry facilities, and barbecue grills.
Jacob's Tanglewood Ranch

Jacob's Tanglewood Ranch

3 out of 5
560 Stockbridge Rd Lee MA
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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.
1805 House Bed and Breakfast

1805 House Bed and Breakfast

3 out of 5
775 Snydertown Road Craryville NY
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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.
Chestnut Lodge

Chestnut Lodge

3.5 out of 5
75 Chestnut Street Lee MA
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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.
Cliffwood Cottage by Evergreen Home

Cliffwood Cottage by Evergreen Home

Lenox MA
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This guesthouse features laundry facilities.
Vanderbilt Lakeside

Vanderbilt Lakeside

3.5 out of 5
161 Main St Philmont NY
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This guesthouse features free WiFi in public areas, wedding services, and free self parking. Enjoy the free continental breakfast each morning. A terrace, a garden, and a communal living room are also on offer.
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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.

Top hotels in Old Chatham

Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!

Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!

Old Chatham NY
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9.6/10 Exceptional! (66 reviews)

Old Chatham Guest Houses essential information

Accommodation
11 Guest Houses
Lowest Price
$93
Highest Price
$346
Popular accommodation
The Central Downtown Inn & Suites, Berkshire Village Carriage House - Super Private!!, The Dewey, Hudson valley and The Berkshires Cottage, Tranquil Retreat - Comfort and Convenience., 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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