
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.
Top Chatham Vacation Deals
Price found within the past 48 hours. Click for updated prices.


Lodges At Cresthaven
per person
Jun. 6 - Jun. 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.4/10 Exceptional! (397 reviews)
The view of Lake George from our balcony was spectacular! We also enjoyed the convenience of lakeside dining on premises at the Boathouse.
Reviewed on Apr. 27, 2025


The Equinox Golf Resort & Spa
per person
Jun. 6 - Jun. 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
7.4/10 Good! (462 reviews)
We a been coming to the Equinox multiple times a year for over 20 years but had not been here in over a year because the last time I was there it was not a pleasant experience. I am happy to say things are back to being very enjoyable again and we will be back soon!
Reviewed on Apr. 25, 2025
Chatham Hotel Deals

Life House Berkshires
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is CA $143 per night from Apr. 30 to May 1
CA $143
CA $159 total
includes taxes & fees
Apr 30 - May 1
9/10 Wonderful! (573 reviews)
Beautiful & Affordable!
"Excellent experience and gorgeous property! Will stay again next time we visit the Berkshires."
Reviewed on Apr. 27, 2025

Comfort Inn Glenmont - Albany South
37 Route 9W, Glenmont, NY
Fully refundable
The price is CA $141 per night from May 7 to May 8
CA $141
CA $161 total
includes taxes & fees
May 7 - May 8
7.8/10 Good! (968 reviews)
"Clean and close to Albany"
Reviewed on Apr. 19, 2025

The Black Swan Lee - Lenox, Ascend Hotel Collection
435 Laurel St, Lee, MA
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Apr. 30 to May 1
CA $151
CA $169 total
includes taxes & fees
Apr 30 - May 1
9/10 Wonderful! (1,006 reviews)
"Friendly staff, great location for hiking and biking in the Berkshires."
Reviewed on Apr. 27, 2025
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.