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Hotels in Chatham

Choose from 1538 Chatham Hotel Deals

Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
  • 5 min drive from The Mac-Haydn Theatre
The price is $108 per night from Apr 8 to Apr 9
$108
includes taxes & fees
Apr 8 - Apr 9
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (535 reviews)
"Motel style building with refreshed modern room. Very clean and the restaurant onsite was good but the breakfast is somewhat limited."

Reviewed on Mar 22, 2025

Life House Berkshires
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
The price is $142 per night from Mar 26 to Mar 27
$142
includes taxes & fees
Mar 26 - Mar 27
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and in-room massages. Our guests praise the helpful staff in ...
8.6/10 Excellent! (1,790 reviews)
"Very nice accomodations, more like a mini apartment than a motel room."

Reviewed on Mar 19, 2025

Vacation Village in the Berkshires
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
The price is $99 per night from Apr 2 to Apr 3
$99
includes taxes & fees
Apr 2 - Apr 3
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! (1,001 reviews)
"They upgraded our room when they found out it was our wedding night. Everything was so nice, the room was extremely clean and beautiful"

Reviewed on Mar 18, 2025

The Yankee, Trademark Collection by Wyndham
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
The price is $147 per night from Mar 26 to Mar 27
$147
includes taxes & fees
Mar 26 - Mar 27
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff in our ...
8.8/10 Excellent! (610 reviews)
"I loved it so much to do"

Reviewed on Mar 19, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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
The price is $178 per night from Apr 14 to Apr 15
$178
includes taxes & fees
Apr 14 - Apr 15
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
8.8/10 Excellent! (1,000 reviews)
"Loved the Inn. Great place and awesome accommodations. Staff, hotel pets, and the building are amazing."

Reviewed on Mar 20, 2025

The Red Lion Inn
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Black Swan Lee - Lenox, Ascend Hotel Collection
3 out of 5
435 Laurel St, Lee, MA
  • 8 min drive from The Mac-Haydn Theatre
The price is $103 per night from Apr 1 to Apr 2
$103
includes taxes & fees
Apr 1 - Apr 2
Stay at this 3-star hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular ...
8.8/10 Excellent! (1,004 reviews)
"Beautiful views of the lake with cozy rooms. Staff is excellent."

Reviewed on Mar 20, 2025

The Black Swan Lee - Lenox, Ascend Hotel Collection
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
The price is $108 per night from Mar 30 to Mar 31
$108
includes taxes & fees
Mar 30 - Mar 31
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! (876 reviews)
"Great property, great staff. Clean rooms"

Reviewed on Mar 24, 2025

Comfort Inn & Suites East Greenbush - Albany
Hotel On North
Hotel On North
3.5 out of 5
297 North Street, Pittsfield, MA
  • 15 min drive from The Mac-Haydn Theatre
The price is $122 per night from Apr 2 to Apr 3
$122
includes taxes & fees
Apr 2 - Apr 3
Stay at this 3.5-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (695 reviews)
Great but noisey on Saturday nights
"This is my second time staying and I love the attention to detail. However I happened to be there on a Saturday in room 202 and I could hear the dj music in my room till 1 am. This seems like it will be a regular Saturday night thing in the dining room. I would inquire about the quietness of your ..."

Reviewed on Mar 12, 2025

Hotel On North
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
The price is $116 per night from Mar 28 to Mar 29
$116
includes taxes & fees
Mar 28 - Mar 29
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (760 reviews)
"Easy check in, nice staff. Rug in the room was kind of musty. They were accommodating to me requesting to have a slightly later check out. Would return if in the area."

Reviewed on Mar 18, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Constance, The Whitlock, & The Dewey By The Lenox Collection
The Constance, The Whitlock, & The Dewey By The Lenox Collection
3.5 out of 5
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
  • 24 min walk from The Mac-Haydn Theatre
The price is $93 per night from Mar 31 to Apr 1
$93
includes taxes & fees
Mar 31 - Apr 1
Stay at this 3.5-star hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.4/10 Very Good! (380 reviews)
Wonderful
"The Constance is so cute! We loved the aesthetic of the building and its proximity to town. We were able to walk to dinner, and Lenox is full of great food spots. The room itself was a great size, with beautiful green walls and old wooden furniture. The shower was to die for and I loved how they ..."

Reviewed on Mar 11, 2025

The Constance, The Whitlock, & The Dewey By The Lenox Collection
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
The price is $109 per night from Apr 13 to Apr 14
$109
includes taxes & fees
Apr 13 - Apr 14
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! (948 reviews)
"Easy check in and"

Reviewed on Mar 23, 2025

Comfort Inn Glenmont - Albany South
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3 out of 5
8 Dan Fox Dr, Pittsfield, MA
  • 9 min drive from The Mac-Haydn Theatre
The price is $144 per night from Apr 4 to Apr 5
$144
includes taxes & fees
Apr 4 - Apr 5
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (442 reviews)
Great family time
"We had a great time at the hotel. My sons and I loved spending time in the pool and the hot tub. The bedroom was spacious, the kitchen had everything we needed, and the bathroom was ample and clean."

Reviewed on Mar 16, 2025

Berkshire Mountain Lodge
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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