Chatham Vacation Packages
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Your Chatham Vacation
The adventure-packed city of Chatham is calling. Delve into everything from its highlights to its hidden gems with a Chatham vacation package that's customized to you. Any trip to Chatham needs a well-planned itinerary. Fill yours with attractions like Martin Van Buren National Historic Site, Art Omi International Arts Center - Fields Sculpture Park and The Mac-Haydn Theatre. Browse Expedia's wide range of travel options and start organizing your ideal vacation to Chatham today.
Chatham Hotel Deals
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is CA $142 per night from Feb 8 to Feb 9
CA $142
CA $174 total
Feb 8 - Feb 9
includes taxes & fees
8.6/10 Excellent! (2,227 reviews)
Spacious 2 bed 2 bath!
Reviewed on Feb 3, 2026
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
282 Cairo Junction Rd Catskill NY
The price is CA $176 per night from Feb 9 to Feb 10
CA $176
CA $250 total
Feb 9 - Feb 10
includes taxes & fees
9.4/10 Exceptional! (140 reviews)
It was an amazing experience. Finding the cabin was a little difficult because I arrived at night time.
Reviewed on Jan 31, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Feb 8 to Feb 9
CA $135
CA $181 total
Feb 8 - Feb 9
includes taxes & fees
9/10 Wonderful! (825 reviews)
We had a lovely extended family weekend here. The staff was outstanding, every staff member was helpful, friendly and courteous. The large room in back of the lobby was especially helpful for our large group to hang out in and be comfortable. Everyone enjoyed the pool and hot tub despite it being ...
Reviewed on Feb 1, 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
