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Hotels in Chatham

Choose from 1507 Chatham Hotel Deals

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 $110 per night from Jan 2 to Jan 3
$110
includes taxes & fees
Jan 2 - Jan 3, 2025
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! (913 reviews)
Great price and clean
"Nice clean hotel but hot tub was working and restaurant was not open. Great hotel for the price."

Reviewed on Dec 15, 2024

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
The price is $108 per night from Jan 1 to Jan 2
$108
includes taxes & fees
Jan 1 - Jan 2, 2025
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)
"This hotel was awesome! We enjoyed the hot tub along with the fireplace in our room!"

Reviewed on Dec 15, 2024

The Yankee, Trademark Collection by Wyndham
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 $144 per night from Jan 6 to Jan 7
$144
includes taxes & fees
Jan 6 - Jan 7, 2025
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)
Heritage stay at an old Inn
"It is one of the oldest inns in America - so it creaks a lot, uneven floors, and for sure that look of old.. not necessarily bad... just a heritage property that has its quirks. We liked it.. the bed could be better for sure... I think that's the main fault.. the restaurant and pub were wonderful, ..."

Reviewed on Dec 16, 2024

The Red Lion Inn
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 $99 per night from Jan 5 to Jan 6
$99
includes taxes & fees
Jan 5 - Jan 6, 2025
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! (455 reviews)
"The coziest best hotel in area! Staff was so wonderful, room was perfect! Lobby bar and lounge is so great."

Reviewed on Dec 19, 2024

Life House Berkshires
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 $122 per night from Jan 12 to Jan 13
$122
includes taxes & fees
Jan 12 - Jan 13, 2025
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! (1,000 reviews)
"Good"

Reviewed on Dec 9, 2024

The Black Swan Lee - Lenox, Ascend Hotel Collection
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3 out of 5
One West Street, Pittsfield, MA
  • 15 min drive from The Mac-Haydn Theatre
The price is $111 per night from Jan 5 to Jan 6
$111
includes taxes & fees
Jan 5 - Jan 6, 2025
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! (701 reviews)
"Staff was very accommodating. The pool area was quite nice and it was deep"

Reviewed on Dec 16, 2024

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Quality Inn
Quality Inn
2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
  • 28 min drive from The Mac-Haydn Theatre
The price is $94 per night from Dec 29 to Dec 30
$94
includes taxes & fees
Dec 29 - Dec 30
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 ...
8/10 Very Good! (1,000 reviews)
"Friendly staff"

Reviewed on Dec 16, 2024

Quality Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
3.5 out of 5
190 Meadow Street, South Lee, MA
  • 15 min drive from The Mac-Haydn Theatre
The price is $158 per night from Jan 9 to Jan 10
$158
includes taxes & fees
Jan 9 - Jan 10, 2025
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! (571 reviews)
"Westayed at the resort for the Stockbridge Christmas weekend location was so convenient to town, dining and events, Resort facilities were extra special pool movie theatre and resort Christmas themed activities would recommend."

Reviewed on Dec 9, 2024

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
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 $216 per night from Jan 1 to Jan 2
$216
includes taxes & fees
Jan 1 - Jan 2, 2025
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a health club, and in-room massages. Our guests praise the helpful staff in our ...
8.6/10 Excellent! (1,748 reviews)
"Nice and quiet family get a way"

Reviewed on Dec 16, 2024

Vacation Village in the Berkshires
voco James Newbury Hudson Valley, an IHG Hotel
voco James Newbury Hudson Valley, an IHG Hotel
3.5 out of 5
60 S River St, Coxsackie, NY
  • 18 min walk from The Mac-Haydn Theatre
The price is $149 per night from Jan 1 to Jan 2
$149
includes taxes & fees
Jan 1 - Jan 2, 2025
Stay at this 3.5-star spa hotel in Coxsackie. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms ...
9.2/10 Wonderful! (226 reviews)
"Love everything about this hotel! We’ll be back again."

Reviewed on Dec 3, 2024

voco James Newbury Hudson Valley, an IHG Hotel
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 $155 per night from Dec 30 to Dec 31
$155
includes taxes & fees
Dec 30 - Dec 31
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! (359 reviews)
"It was amazing! The staff was incredible, the room was very clean and cozy, and overall was a great place to stay. Loved it here!"

Reviewed on Dec 21, 2024

The Constance, The Whitlock, & The Dewey By The Lenox Collection
Four Points by Sheraton Albany
Four Points by Sheraton Albany
3 out of 5
3 Mount Hope Way, Albany, NY
  • 45 min drive from The Mac-Haydn Theatre
The price is $139 per night from Dec 26 to Dec 27
$139
includes taxes & fees
Dec 26 - Dec 27
Stay at this 3-star business-friendly hotel in Albany. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
8.8/10 Excellent! (403 reviews)
"Easily accessible from thr I87"

Reviewed on Dec 20, 2024

Four Points by Sheraton 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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