Book Hotels in Chatham, NY
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Top Chatham hotels
The Yankee Inn
"I got the impression that Yankee Inn has quite a history, although it has been recently updated and renovated. The staff were available and friendly. At times I felt I was on a 1950s movie set, imagining Bing Crosby singing in my head. I ultimately extended my stay because it's location was a hub ..."
Reviewed on Jun 8, 2026
Berkshire Mountain Lodge
"Great property and very nice condo unit with full kitchen. Everything I needed and very convenient location with good amenities overall. Would stay here again."
Reviewed on Jun 9, 2026
Berkshires Untold
"The hotel was beautiful. My room was very nice exactly what I needed. The decor was very inviting and the bathroom was amazingly beautiful as well as the lounge and grounds of the property. My only one wish was that there was coffee in the room. Although you just had to walk to the lobby to get coffee ..."
Reviewed on Jun 8, 2026
Vacation Village in the Berkshires
"This is a big beautful modern condo complex about 20 mins outside Wiilamstown (to the north) or Pittsfield (to the south). Huge swimming pools - one indoors, one out. Beautiful views of the Berkshires. Quiet rural environment. I could hear the frogs singing and the cricketa chirp at night. Excellent ..."
Reviewed on Jun 8, 2026
The Red Lion Inn
"It is a charming, historic hotel. Dinner in the tavern was delicious and service was very good. The only thing we didn't like was the mattress, which needs to be replaced as it has divits. Other than that, it's a cool place that is fun to explore. Wish we were here longer to try out the pool. We ..."
Reviewed on Jun 8, 2026
Quality Inn Great Barrington
"Excellent location, great low price, VERY Comfortable bed- throwback era motel. Why pay more when it’s all here!"
Reviewed on Jun 7, 2026
Comfort Inn & Suites East Greenbush - Albany
"This was a lovely, clean, and comfortable stay. The location was just a few miles from tons of shopping and dining. The included breakfast was tasty and had lots of options. We would absolutely stay again if in the area."
Reviewed on Jun 9, 2026
Country Inn & Suites by Radisson, Downtown Albany New York
"It had zero of the amenities that I had booked the hotel for. They need to update their website because none of the amenities listed on there are at the hotel."
Reviewed on Jun 7, 2026
Comfort Inn Glenmont - Albany South
"Clean room, friendly staff"
Reviewed on Jun 8, 2026
Chatham Hotel & Travel Guide\n
There isn't a big range of places to stay within easy driving distance of Chatham's center. Be sure to book well in advance if you'd like to stay close to Chatham's action.
The Inn At Richmond, Massachusetts, which is the nearest hotel, is 11 miles (18 kilometers) from the heart of downtown Chatham. A second handy Travelocity-listed option is the Wyndham Bentley Brook, which is situated in Massachusetts, 20 miles (33 kilometers) from the center of Chatham.
The Stockbridge Country Inn is 12 miles (19 kilometers) from the center of Chatham. Also, the Fairfield Inn and Suites by Marriott Lenox Great Barrington is situated 14 miles (23 kilometers) away. You might like to check in to the Holiday Inn Express Hotel & Suites Great Barrington or the Jiminy Peak Mountain Resort.
After you've thoroughly explored Chatham, why don't you discover a little more of the region? The Hudson Valley vicinity boasts plenty of things to check out. Explore Hudson Valley's historic bridges and don't forget to fall in love with the area's rivers. Enlightened travelers in this corner of United States of America enjoy rock climbing and hiking.
On the hunt for things to do? You could spend a few hours seeing Marist College and Culinary Institute of America, which can be found in Poughkeepsie, 50 miles (77 kilometers) southwest of Chatham. When you visit Poughkeepsie, be sure to check out the Buttermilk Falls Inn and Residence Inn by Marriott Poughkeepsie. 35 miles (58 kilometers) southwest of Chatham, you will reach Kingston, home to the Best Western Plus Kingston Hotel And Conference Center and Hampton Inn Kingston. The El Paso Winery and Old Dutch Church are popular places to experience when in Kingston.
Prior to departing from Hudson Valley, you sure ensure you enjoy enthusiastic locals watching an exciting game of sport. Make your way to Times Union Center, located to the northwest of Chatham. For tourists who like the thought of staying close to the game, book a room in the Hilton Albany or TownePlace Suites by Marriott Albany Downtown/Medical Center.
When you are traveling through Albany International Airport and hope to book a room in the area, have a look at Albany Marriott or Homewood Suites by Hilton Albany.
Frequently asked questions
Recent Chatham hotel reviews by fellow wanderers
Berkshire Mountain Lodge
"Great property and very nice condo unit with full kitchen. Everything I needed and very convenient location with good amenities overall. Would stay here again."
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