Chatham Vacations from $775
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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.
The Latest Chatham vacation packages
Price found within the past 48 hours. Click for updated prices.
The Ponds at Foxhollow
Price was $962, price is now $775 per person
$775
per person
Sep 17 - Sep 20
found 3 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Albany (ALB)
8.6/10 Excellent! (141 reviews)
I had not visited the Ponds for 30 years. It has not gracefully aged. Condo unit has not been updated since it was built in the early 70s and it shows. Drafty and slightly damaged doors, slow drains in the bathrooms, furniture and rugs that show damage and age, and a clubhouse in need of updating. Front desk staff not very friendly or useful, odd because they don’t have a lot of foot traffic this time of the season. There are other similar facilities in the area that might be worth exploring versus this tired old place.
Reviewed on Feb 9, 2026
The Cornell Inn, Lenox & The Berkshires
Price was $1,339, price is now $1,062 per person
$1,062
per person
Sep 17 - Sep 20
found 3 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Albany (ALB)
9.2/10 Wonderful! (1,003 reviews)
Staff was helpful and friendly. Breakfast was amazing. The grounds are so beautiful . There were a number of lovely places inside and out for sitting and relaxing. We loved the welcome drink and a bottle of wine ( choice of red or white) to have in our room. We enjoyed it on our balcony with its lovely views of the main house and the yard. Unfortunately we couldn’t attend the cognac tasting as we were busy. I would love to come to the Cornell again-and again!
Reviewed on Jun 26, 2026
Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay
Price was $1,479, price is now $1,177 per person
$1,177
per person
Sep 17 - Sep 20
found 3 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Albany (ALB)
10/10 Exceptional! (1 review)
Such a beautiful time was spent here with my family for my nephews graduation from university at Albany. We feed the birds, played family games, got in the hot tub.
Reviewed on May 23, 2026
Stay near popular Chatham attractions
Chatham Hotel Deals
Country Inn & Suites by Radisson, Downtown Albany New York
300 Broadway Albany NY
Fully refundable
$103 nightly
The price is $117 total per night from Jul 12 to Jul 13
$117 total
Jul 12 - Jul 13
Total with taxes and fees
8/10 Very Good! (757 reviews)
"Great location to attend concerts. Have stayed here several times. Staff is friendly & helpful. Requested a late checkout & no hesitation by staff to accommodate. Room was great. Breakfast was decent as well."
Reviewed on Jul 1, 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
$139 nightly
The price is $156 total per night from Jul 6 to Jul 7
$156 total
Jul 6 - Jul 7
Total with taxes and fees
8.8/10 Excellent! (2,412 reviews)
"Staff was super friendly, splash pad was being renovated so that wasn’t available m.. we had fun but hate that check in is so late and check out so early!"
Reviewed on Jun 30, 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
$155 nightly
The price is $173 total per night from Jul 6 to Jul 7
$173 total
Jul 6 - Jul 7
Total with taxes and fees
9.2/10 Wonderful! (1,011 reviews)
"The friendly atmosphere coming from the staff."
Reviewed on Jun 30, 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.
Find the Best Chatham Vacation Packages
Chatham Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Albany Intl. Airport (ALB) |
Population | 1,700 |
Max Temp Winter | 30ºF |
Max Temp Summer | 80ºF |
Top Sights | The Mac-Haydn Theatre, Shaker Museum and Library and Hudson Chatham Winery |
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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.
