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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Chatham inns

A room with a large sliding glass door leading to a balcony with cherry blossom trees.

1. Wm. Farmer & Sons

Wm. Farmer & Sons
2.5 star property
Hudson
9.2 out of 10, Wonderful, (124 reviews)
"Great bar and restaurant right on property."
United States
Lori
The price is AED 645
AED 729 total
includes taxes & fees
6 Dec - 7 Dec
Wm. Farmer & Sons
A dining table set for two with red plates, silverware, and a wine glass, viewed through a window overlooking a red building.

2. Gregory House Country Inn

Gregory House Country Inn
3.0 star property
Averill Park
8.8 out of 10, Excellent, (164 reviews)
"Both the room and the restaurant were very good! we enjoyed our stay and the food was excellent!"
United States
daniel
The price is AED 413
AED 459 total
includes taxes & fees
7 Nov - 8 Nov
Gregory House Country Inn
A dining area with round tables set for two, a fireplace, and a mural on the wall.

3. The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (96 reviews)
"Lovely property.unique historic buildings and rooms with updated amenities! Quiet and peaceful beautiful dinner!"
United States
mary ellen
The price is AED 1,065
AED 1,285 total
includes taxes & fees
8 Nov - 9 Nov
The Old Inn On The Green
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.
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Learn more about Chatham

This charming upstate village hosts the Mac-Haydn Theatre's summer productions and a vibrant Main Street with independent shops and cafés. Explore the historic Union Station or time your visit for the Columbia County Fair, a beloved local tradition since 1841.

See all hotels in Chatham
A brick building with a green dome and columns, labeled "TRACY MEMORIAL VILLAGE HALL".

Top reviews in Chatham

A room with a large sliding glass door leading to a balcony with cherry blossom trees.
Wm. Farmer & Sons

Wm. Farmer & Sons

Wm. Farmer & Sons
Hudson

10/10 Excellent

WM Farmer & Sons was a great boutique hotel. Location is amazing! We stayed in the Mercer suite & I would highly recommend. Great amenities, bed was unbelievably comfortable, and quiet. The common areas and outdoor space were beautiful. I will look forward to staying at this property again. We were there on a Wednesday and unfortunately, the restaurant was closed. Staff were great before, during, and after our stay. Absolutely 5 STARS
United States
Stacy
Reviewed October 20, 2026
Wm. Farmer & Sons

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