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Choose from 1626 Chatham Hotel Deals

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! (962 reviews)
"We love the Bershire Mountain Lodge. We've stayed here five other times but this time we do have a few very minor negatives. 1) The cabinet door under the kitchenette sink had a loose hinge. We messaged the staff and requested that they wait until after we checked out to repair the hinge. We hope ..."

Reviewed on Jun 4, 2026

Berkshire Mountain Lodge
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 Colonie Center Mall and Irish American ...
8/10 Very Good! (677 reviews)
"Too much noise from traffic at night not peaceful sleep. They closed the breakfast before the time . About this property breakfast time is Full breakfast included Served daily from 6:30 AM - 10:00 AM We were there 9:35 and it was closed. I tell to the receptionist that’s the time online. She was ..."

Reviewed on Jun 5, 2026

Country Inn & Suites by Radisson, Downtown Albany New York
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! (2,389 reviews)
"Great place just listed again for four more nights"

Reviewed on Jun 3, 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! (1,003 reviews)
"Beautiful and well maintained and close to shipping and food"

Reviewed on May 29, 2026

The Yankee Inn
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! (972 reviews)
"Here’s what we liked: If we were just reviewing BERKSHIRES UNTOLD based on the staff, we’d be giving it a 5. The staff were extremely friendly, helpful and gracious. When we asked for extra towels and requested a room change, they accommodated those requests immediately. After we switched rooms they ..."

Reviewed on Jun 4, 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! (1,002 reviews)
"Very Charming hotel. Good size rooms, has many interesting features due to the age of the hotel. Takes you back to another era."

Reviewed on Jun 2, 2026

The Red Lion Inn
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! (1,001 reviews)
"Parking is free"

Reviewed on Jun 5, 2026

Comfort Inn Glenmont - Albany South
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! (1,001 reviews)
"Everything was great,the staff was very nice and everything went well."

Reviewed on Jun 2, 2026

Comfort Inn & Suites East Greenbush - Albany
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! (239 reviews)
"I went on a solo cabin trip and it was so relaxed and peaceful! The condition of the cabin was better than I expected it to be and the staff were super friendly and accommodating. Definitely plan to go again next year! The cabin had so many supplies from cooking material, mini fridge (no freezer ..."

Reviewed on Jun 5, 2026

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
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! (904 reviews)
"Spacious well-equipped units. Staff was friendly and helpful. Activity center was very nice. Would definitely stay again"

Reviewed on May 28, 2026

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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! (863 reviews)
"Hotels Amazing stay here"

Reviewed on May 29, 2026

Hotel On North
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! (1,001 reviews)
"Hotel was fine with the exception of nearby train coming through in the middle of the night."

Reviewed on Jun 2, 2026

Quality Inn Great Barrington
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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