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Hotels in Chatham

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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 ...
8.6/10 Excellent! (2,179 reviews)
My stay was great with no problems.

Reviewed on Dec 19, 2025

Vacation Village in the Berkshires
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! (1,000 reviews)
Very clean and modern room with comfortable beds.

Reviewed on Nov 29, 2025

Comfort Inn Glenmont - Albany South
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

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 ...
9/10 Wonderful! (1,006 reviews)
The room is so spotless, bathroom is so luxurious! The bed is so soft and sleep very quickly! The staffs are so great! Quick to answer to my questions and my needs. Definitely come back again to stay!

Reviewed on Dec 22, 2025

The Yankee, Trademark Collection by Wyndham
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West 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 breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (993 reviews)
N/a

Reviewed on Dec 20, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
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 ...
9.4/10 Exceptional! (111 reviews)
Cozy and quaint cabin. It had most amenities we expected ex: kitchen utensils, paper towels, coffee & tea. The night we stayed dropped to the single digits but the cabin was well insulated and maintained its heat. So much that we didn’t turn on the heat throughout the night, there seems to be a heat ...

Reviewed on Dec 20, 2025

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
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! (793 reviews)
Spacious room and loved pool and hot tub!

Reviewed on Dec 19, 2025

Berkshire Mountain Lodge
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, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (1,002 reviews)
I had always wanted to stay at The Red Lion Inn and decided to treat myself to a one-night stay. Since it was in December I was especially excited to have a fireplace in the room. Sadly, I learned the fireplace didn’t work and that they are renovating some of the systems, but offered no partial refund ...

Reviewed on Dec 23, 2025

The Red Lion 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! (817 reviews)
Room was very nice and spacious!

Reviewed on Dec 14, 2025

Berkshires Untold
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 ...
9/10 Wonderful! (806 reviews)
very good stay my only recommendation would be to have more coffee supplies as their is only enough for one pot of coffee and we were staying two days other than that very peaceful and comfortable.

Reviewed on Dec 22, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
549 Washington Street Hudson NY
  • 19 min drive from The Mac-Haydn Theatre
Book a stay at this spa hotel in Hudson. Enjoy free WiFi, a full-service spa, and a 24-hour front desk. Popular attractions Hudson Area Library and Stoddard ...
8/10 Very Good! (11 reviews)
This was a very cool new hotel. Easy walk into the cute town of Hudson. They are still working out some kinks, we didn’t have hot water but staff was very understanding and offered us

Reviewed on Dec 9, 2025

Pocketbook Hotel and Bath
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 out of 5
415 Stockbridge Rd Great Barrington MA
  • 25 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 helpful staff and the ...
8.8/10 Excellent! (710 reviews)
The room was super clean and comfortable. Nice television and great bathroom. Highly recommend!

Reviewed on Dec 21, 2025

Holiday Inn Express Hotel & Suites Great Barrington by IHG
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 ...
8.4/10 Very Good! (1,000 reviews)
Really enjoyed our overnight mid-trip stay here. The facility is open and bright, clean and prep'd. The staff (including late-night check-in clerk) were all very friendly and outgoing. The breakfast was a cut above, including a couple waffle makers, some well-prepared scrambled eggs and crispy bacon ...

Reviewed on Dec 23, 2025

Comfort Inn & Suites East Greenbush - Albany
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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