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Hotels in Chatham

Choose from 1632 Chatham Hotel Deals

Country Inn & Suites by Radisson, Downtown Albany New York

Country Inn & Suites by Radisson, Downtown Albany New York

3 out of 5
300 Broadway Albany NY
  • 48 min drive from The Mac-Haydn Theatre
Book a stay at this business-friendly hotel in Albany. Enjoy free breakfast, free WiFi, and free parking. Popular attractions MVP Arena and Colonie Center Mall ...
8/10 Very Good! (695 reviews)
"Very convenient location just off 787 in downtown Albany. Quite nice for the price. I appreciated the spacious breakfast room and the easy, free parking. Gracious hosts, too."

Reviewed on Jun 10, 2026

Country Inn & Suites by Radisson, Downtown Albany New York
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
  • 9 min drive from The Mac-Haydn Theatre
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (974 reviews)
"Staff, breakfast, spaciousness of the room, all fabulous."

Reviewed on Jun 11, 2026

Berkshire Mountain Lodge
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
  • 34 min drive from The Mac-Haydn Theatre
Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,392 reviews)
"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

Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
  • 8 min drive from The Mac-Haydn Theatre
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9.2/10 Wonderful! (1,012 reviews)
"The room was large, clean and comfortable. The location was near shopping and dining. The check in was quick and pleasant."

Reviewed on Jun 11, 2026

The Yankee Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
  • 28 min drive from The Mac-Haydn Theatre
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,000 reviews)
"Excellent location, great low price, VERY Comfortable bed- throwback era motel. Why pay more when it’s all here!"

Reviewed on Jun 7, 2026

Quality Inn Great Barrington
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
  • 5 min drive from The Mac-Haydn Theatre
Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
9/10 Wonderful! (982 reviews)
"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

Berkshires Untold
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
  • 14 min drive from The Mac-Haydn Theatre
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,006 reviews)
"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

The Red Lion Inn
Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

2.5 out of 5
99 Miller Rd Castleton-on-Hudson NY
  • 37 min drive from The Mac-Haydn Theatre
Book a stay at this business-friendly hotel in Castleton-on-Hudson. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the ...
8.6/10 Excellent! (1,002 reviews)
"Enjoyed the breakfast and pool"

Reviewed on Jun 9, 2026

Comfort Inn & Suites East Greenbush - Albany
Comfort Inn Glenmont - Albany South

Comfort Inn Glenmont - Albany South

2.5 out of 5
37 Route 9W Glenmont NY
  • 44 min drive from The Mac-Haydn Theatre
Book a stay at this business-friendly hotel in Glenmont. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
7.8/10 Good! (1,002 reviews)
"Including breakfast"

Reviewed on Jun 11, 2026

Comfort Inn Glenmont - Albany South
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2 out of 5
282 Cairo Junction Rd Catskill NY
  • 19 min drive from The Mac-Haydn Theatre
Stay at this cabin in Catskill. Enjoy free parking, furnished patios, and climate control. Popular attractions Catskill Golf Club and Angelo Canna Town Park ...
9.6/10 Exceptional! (246 reviews)
"Good for a getaway"

Reviewed on Jun 11, 2026

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
  • 15 min drive from The Mac-Haydn Theatre
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
9.6/10 Exceptional! (864 reviews)
"Hotels Amazing stay here"

Reviewed on May 29, 2026

Hotel On North
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street South Lee MA
  • 15 min drive from The Mac-Haydn Theatre
Book a stay at this family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in ...
9.2/10 Wonderful! (908 reviews)
"Love it here. Staff is amazing and beautiful units and resort :)"

Reviewed on Jun 11, 2026

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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.

Find cheap hotels in Chatham

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