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Hotels in Chatham

Choose from 1621 Chatham Hotel Deals

Country Inn & Suites by Radisson, Downtown Albany New York

Country Inn & Suites by Radisson, Downtown Albany New York

2.5 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! (762 reviews)
"Property was between two abandoned buildings and the highway. Did not feel safe or secure at all. Shower didn’t work and the lighting was dim. Part of our group got stuck in an elevator and doors had to be prayed open and kids lifted out between floors."

Reviewed on Jul 2, 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! (2,414 reviews)
"Clean large room- some wear on the kitchen cabinets and the bathroom door stuck check in was a bit of a challenge. Otherwise good"

Reviewed on Jul 1, 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! (1,000 reviews)
"The Yankee Inn was a convenient and affordable option for our visit to Tanglewood. The check-in staff was friendly and advised us of breakfast and checkout hours. The room was clean and thankfully well air conditioned during our stay there in 90 degree weather! The included breakfast was typical ..."

Reviewed on Jul 2, 2026

The Yankee Inn
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! (1,010 reviews)
"The hotel was nice, full kitchen and quiet large for our family of four. We had a one bedroom suite, tucked into a corner of the hotel. Location was quiet, on the main floor. Pool and hot tub were nice. The sofa bed was not comfortable, at all. It would be worth the hotel replacing the sofa bed, ..."

Reviewed on Jul 2, 2026

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, free parking, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,000 reviews)
"Staff was great. Cool place - so historic"

Reviewed on Jun 30, 2026

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! (997 reviews)
"Nice place to stay."

Reviewed on Jul 1, 2026

Berkshires Untold
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! (1,003 reviews)
"AC was not working in our room. They took 2 hours in fixing it."

Reviewed on Jul 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

2.5 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! (253 reviews)
"I brought my wife to the Poscard Cabin because a friend of owers told me about it. I have to tell you my wife had a blast we came here to celebrate her 66th Birthay and ower 20 years anniversary and it was the best choice I made. I will recommend to everyone I know."

Reviewed on Jul 1, 2026

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
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)
"Room was spacious and clean with a comfortable bed. Easy parking, nice quiet location. Easy walk to town."

Reviewed on Jul 1, 2026

Quality Inn Great Barrington
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
  • 8 min drive from The Mac-Haydn Theatre
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and ...
9.4/10 Exceptional! (119 reviews)
"It was generally excellent. The only difficultly I found was using the TV and that thermostat. A little too hi- tech"

Reviewed on Jul 2, 2026

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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)
"What I did not like was EXPEDIA!!!!! When I looked up this hotel (that I have used before!!!) this is the price that showed › 5 Best Seller Best value! 1 King Bed Our Best Rate Pay Now & Save Also comes with: Free Breakfast Free Parking Partially refundable $105.00night i $138total Book now Also ..."

Reviewed on Jun 30, 2026

Comfort Inn Glenmont - Albany South
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

2.5 out of 5
170 Housatonic Street Lee MA
  • 11 min drive from The Mac-Haydn Theatre
Book a stay at this business-friendly hotel in Lee. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (1,001 reviews)
"A great budget stay in Berkshires."

Reviewed on Jul 2, 2026

Quality Inn Lee - Lenox South
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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