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Hotels in Chatham

Choose from 1540 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 $119 per night from May 4 to May 5
$119
includes taxes & fees
May 4 - May 5
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! (549 reviews)
"Love the decor, amazing value for price"

Reviewed on Apr 11, 2025

Life House 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 23 to Apr 24
$99
includes taxes & fees
Apr 23 - Apr 24
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! (1,002 reviews)
"Most everything was good. They were doing major renovation! Beds were decent, shower was nice, free breakfast buffet was great, lots to choose from! Pool was nice, but only 5 feet, but jacuzzi was wonderful! Heat was very noisy, though. Just a couple things they could have explained better in the ..."

Reviewed on Apr 10, 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 $134 per night from Apr 28 to Apr 29
$134
includes taxes & fees
Apr 28 - Apr 29
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
9/10 Wonderful! (618 reviews)
"Great deal for villa resort suite. Lots of space, great condition, great amenities, great location."

Reviewed on Apr 12, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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 $75 per night from Apr 28 to Apr 29
$75
includes taxes & fees
Apr 28 - Apr 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 ...
8.2/10 Very Good! (1,001 reviews)
"We like Great Barrington. This is a great location. This is a great value.. We will be back."

Reviewed on Mar 29, 2025

Quality Inn
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 Apr 17 to Apr 18
$211
includes taxes & fees
Apr 17 - Apr 18
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)
"Quaint & hospitable!"

Reviewed on Apr 13, 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 28 to Apr 29
$103
includes taxes & fees
Apr 28 - Apr 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! (1,003 reviews)
"The continental breakfast was amazing in my opinion. Huge selection. The staff were courteous and friendly. The room was clean and I am very ocd . We would definitely recommend to our friends. We would like to return during summer as there is so much to do during summer time. Overall this was a very ..."

Reviewed on Apr 12, 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 $118 per night from May 11 to May 12
$118
includes taxes & fees
May 11 - May 12
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! (890 reviews)
"It was a clean & a very nice hotel , very nice staff"

Reviewed on Apr 14, 2025

Comfort Inn & Suites East Greenbush - Albany
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 $91 per night from May 4 to May 5
$91
includes taxes & fees
May 4 - May 5
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! (382 reviews)
"Lovely location!"

Reviewed on Apr 4, 2025

The Constance, The Whitlock, & The Dewey By The Lenox 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 $131 per night from Apr 27 to Apr 28
$131
includes taxes & fees
Apr 27 - Apr 28
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! (702 reviews)
"Comfortably laid out with a sitting area and artwork and decor is very cool."

Reviewed on Apr 11, 2025

Hotel On North
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 $135 per night from Apr 28 to Apr 29
$135
includes taxes & fees
Apr 28 - Apr 29
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! (1,794 reviews)
"The location to jimney peak was great."

Reviewed on Mar 26, 2025

Vacation Village in the Berkshires
Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham Lenox
2 out of 5
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
  • 7 min drive from The Mac-Haydn Theatre
The price is $84 per night from May 1 to May 2
$84
includes taxes & fees
May 1 - May 2
Stay at this motel in Lenox. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.6/10 Good! (716 reviews)
Nice value for room.
"Staff friendly. Room comfortable. Location great."

Reviewed on Apr 1, 2025

Howard Johnson by Wyndham Lenox
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 $113 per night from Apr 20 to Apr 21
$113
includes taxes & fees
Apr 20 - Apr 21
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! (959 reviews)
"The room we had was very clean and looks like it was just repainted. The staff were awesome! Looked like a family owned business. Staff were super friendly and helpful. I would definitely recommend this Comfort Inn to stay at! Very happy with the accommodations!"

Reviewed on Apr 10, 2025

Comfort Inn Glenmont - Albany 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.

Find cheap hotels in Chatham

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