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Hotels in Chatham

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Choose from 1537 Chatham Hotel Deals

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 $137 per night from Mar 9 to Mar 10
$137
includes taxes & fees
Mar 9 - Mar 10
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! (1,762 reviews)
"Super clean and spacious. Rooms have everything you need for a long stay."

Reviewed on Feb 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
The price is $108 per night from Mar 2 to Mar 3
$108
includes taxes & fees
Mar 2 - Mar 3
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! (932 reviews)
"It was very easy to park"

Reviewed on Feb 18, 2025

Comfort Inn Glenmont - Albany South
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 Mar 9 to Mar 10
$108
includes taxes & fees
Mar 9 - Mar 10
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! (503 reviews)
Looks nice but is eh
"Life House Berkshires looks great, but no one actually works there. Or at least that's how it seemed during our stay. I never got the welcome text they said I would get to be able to communicate with staff. I called the 800 number once to try to get someone and couldn't get a person. I finally did ..."

Reviewed on Feb 19, 2025

Life House Berkshires
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 $147 per night from Feb 24 to Feb 25
$147
includes taxes & fees
Feb 24 - Feb 25
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! (595 reviews)
Greatness
"It was a great little getaway from the city, service was great and helpful nothing to complain about this spot"

Reviewed on Feb 10, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
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 $211 per night from Feb 24 to Feb 25
$211
includes taxes & fees
Feb 24 - Feb 25
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! (1,001 reviews)
"The heated pool . Nice to go outside for a swim when it's 23 degrees outside ."

Reviewed on Feb 19, 2025

The Red Lion Inn
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 $116 per night from Feb 28 to Mar 1
$116
includes taxes & fees
Feb 28 - Mar 1
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! (738 reviews)
Dated but trying
"Great for the money. Unfortunately the jacuzzi was non-functional which was the one thing I was looking forward to after a ski day. Hotel staff was amazing."

Reviewed on Feb 17, 2025

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
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 $89 per night from Mar 2 to Mar 3
$89
includes taxes & fees
Mar 2 - Mar 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! (1,000 reviews)
"Staff was super nice, the rooms were really nice and clean."

Reviewed on Feb 17, 2025

The Yankee, Trademark Collection by Wyndham
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 $131 per night from Mar 23 to Mar 24
$131
includes taxes & fees
Mar 23 - Mar 24
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! (432 reviews)
Easy spot for an overnight!
"We had a great stay. Pool was great, room was good, the pull out couch was a little uncomfortable, but when aren't they. The game room needed updating as one arcade machine was broken. Kitchen was great in the room, and the whole hotel had a good vibe to it!"

Reviewed on Feb 10, 2025

Berkshire Mountain Lodge
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 Mar 2 to Mar 3
$122
includes taxes & fees
Mar 2 - Mar 3
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! (1,002 reviews)
"Two adults and a baby to enjoy winter wonderland: it worked very well! Very close to everything!"

Reviewed on Feb 19, 2025

The Black Swan Lee - Lenox, Ascend Hotel Collection
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 Mar 2 to Mar 3
$122
includes taxes & fees
Mar 2 - Mar 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! (684 reviews)
"Amazing place to stay. So unique and cozy! I would stay there everytime l visited Pittsfield but its always booked because its so popular."

Reviewed on Feb 12, 2025

Hotel On North
The Little Lion
The Little Lion
3 out of 5
506 Stockbridge Road, Great Barrington, MA
  • 20 min drive from The Mac-Haydn Theatre
The price is $71 per night from Mar 9 to Mar 10
$71
includes taxes & fees
Mar 9 - Mar 10
Stay at this 3-star motel in Great Barrington. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular ...
8.6/10 Excellent! (473 reviews)
"Easy check in. No disturbances. Cute rooms. Disappointed there was no availability for my last trip to GB because I would have loved to stay here one last time."

Reviewed on Feb 20, 2025

The Little Lion
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 $85 per night from Mar 9 to Mar 10
$85
includes taxes & fees
Mar 9 - Mar 10
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)
"Very good stay at the Quality Inn!"

Reviewed on Feb 17, 2025

Quality Inn
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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