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Hotels in Chatham

Choose from 1517 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 Feb 5 to Feb 6
$108
includes taxes & fees
Feb 5 - Feb 6
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! (479 reviews)
"I love this place! The staff is friendly, helpful and accommodating. The lobby and rooms are updated and gorgeous! There is an onsite bar and restaurant.Great location, minutes from restaurants and shopping (Lee Outlets, Marshall's and quaint boutiques)."

Reviewed on Jan 17, 2025

Life House 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 $106 per night from Jan 31 to Feb 1
$106
includes taxes & fees
Jan 31 - Feb 1
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! (922 reviews)
Nice stay
"Great night sleep & close to all my needs"

Reviewed on Jan 19, 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
The price is $115 per night from Jan 30 to Jan 31
$115
includes taxes & fees
Jan 30 - Jan 31
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! (1,003 reviews)
"Had a great time at this hotel. The rooms are comfortable. The staff is very friendly. Ended up spending Friday and Saturday night hanging out in the bar in the hotel where Carl and George kept us entertained. We had a lot of unexpected fun (I’m not one to hang out in a bar but felt at home)"

Reviewed on Jan 19, 2025

The Yankee, Trademark Collection by Wyndham
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 Jan 27 to Jan 28
$147
includes taxes & fees
Jan 27 - Jan 28
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! (585 reviews)
Quiet winter break
"Great place for a quiet winter break. Kitchen was well-equipped and everything was in working order and spotlessly clean"

Reviewed on Jan 17, 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 $146 per night from Jan 29 to Jan 30
$146
includes taxes & fees
Jan 29 - Jan 30
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)
"Little disappointed with the service in the Dining Room. Bar closed early which was disappointing in the sense there was nothing to do after hours."

Reviewed on Jan 14, 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 $118 per night from Jan 24 to Jan 25
$118
includes taxes & fees
Jan 24 - Jan 25
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! (727 reviews)
Reliable, friendly
"Appreciated that the hotel offered free valet, especially given how cold it was. Check in was fast, courteous. Room was spacious and clean. Breakfast was good, reasonably priced. Check out was speedy and friendly. Hotel was still decorated for the holidays which made it festive looking. Could use ..."

Reviewed on Jan 13, 2025

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
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 $113 per night from Jan 28 to Jan 29
$113
includes taxes & fees
Jan 28 - Jan 29
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 ...
9/10 Wonderful! (1,002 reviews)
Great affordable but nice option
"Excellent affordable option with a very pretty view of the lake. The 24 hour coffee and tea stand was also great. Staff were very polite and helpful. Room was very clean. Would definitely stay here again."

Reviewed on Jan 19, 2025

The Black Swan Lee - Lenox, Ascend Hotel Collection
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 23 to Jan 24
$216
includes taxes & fees
Jan 23 - Jan 24
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! (1,755 reviews)
"It had a great pool and hot tub. also right near the ski area, jiminey Peak."

Reviewed on Jan 20, 2025

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 $153 per night from Jan 26 to Jan 27
$153
includes taxes & fees
Jan 26 - Jan 27
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! (238 reviews)
"Well maintained property and very attentive staff."

Reviewed on Jan 20, 2025

voco James Newbury Hudson Valley, an IHG Hotel
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 $145 per night from Jan 26 to Jan 27
$145
includes taxes & fees
Jan 26 - Jan 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! (412 reviews)
"Very clean, quiet , convenient hotel. Appreciate the pool."

Reviewed on Jan 10, 2025

Four Points by Sheraton Albany
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 Jan 28 to Jan 29
$94
includes taxes & fees
Jan 28 - Jan 29
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! (1,001 reviews)
"Good area, close to the restaurant and shop"

Reviewed on Jan 8, 2025

Quality Inn
Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox
2.5 out of 5
445 Pittsfield Rd, Lenox, MA
  • 7 min drive from The Mac-Haydn Theatre
The price is $141 per night from Jan 28 to Jan 29
$141
includes taxes & fees
Jan 28 - Jan 29
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 helpful staff ...
9.2/10 Wonderful! (999 reviews)
"Nice pool and breakfast. Exactly like my previous experiences at Hampton Inn except this was probably the the fewest people I've encountered when staying with this chain. It was very quiet. Had the pool to ourselves for an hour."

Reviewed on Jan 5, 2025

Hampton Inn & Suites Berkshires-Lenox
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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