Chatham Vacations from $602
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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 Cornell Inn, Lenox & The Berkshires
Save 100% on your flight
per person
Aug 15 - Aug 18
found 16 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
9/10 Wonderful! (1,000 reviews)
Cornell Inn was lovely. The place is so clean- and I’m a germaphobe! The staff was kind, helpful and welcoming. The breakfast was delicious and served outside in a beautiful garden. Would definitely recommend.
Reviewed on Jul 7, 2025
Discover the most popular places to visit in Chatham
The Mac-Haydn Theatre
You can enjoy a show at The Mac-Haydn Theatre on your trip to Chatham. Stroll along this trendy area's riverfront, or simply enjoy its coffeehouses.
Chatham Hotel Deals
Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $115 total per night from Jul 13 to Jul 14
$115 total
Jul 13 - Jul 14
Total includes taxes and fees
8.6/10 Excellent! (1,860 reviews)
"Activities look good during week but we miss them on our weekend stay"
Reviewed on Jul 8, 2025
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $141 total per night from Jul 15 to Jul 16
$141 total
Jul 15 - Jul 16
Total includes taxes and fees
8.4/10 Very Good! (1,008 reviews)
"Great stay"
Reviewed on Jul 5, 2025
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $170 total per night from Jul 16 to Jul 17
$170 total
Jul 16 - Jul 17
Total includes taxes and fees
9/10 Wonderful! (667 reviews)
"Very good"
Reviewed on Jul 7, 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.
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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- Hotels near The Mac-Haydn Theatre
- Ghent Hotels
- Vacation Homes in Ghent
- Motels in Ghent
- Hotels near Hudson Chatham Winery
- Hotels near Art Omi International Arts Center - Fields Sculpture Park
- Hotels near Omi International Arts Center
- East Chatham Hotels
- 4 Star Hotels in East Chatham
- B&B in East Chatham
- Apartments in East Chatham
- Hotels near Van Alen House
- Valatie Hotels
- Motels in Valatie
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- Hotels near Shaker Museum and Library
- Old Chatham Hotels
- B&B in Old Chatham
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- RV Parks in Old Chatham
- 4 Star Hotels in Old Chatham
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- Hotels near Martin Van Buren National Historic Site
- Kinderhook Hotels
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- Malden Bridge Hotels
- North Chatham Hotels
- The Mac-Haydn Theatre
- Visit Ghent
- Art Omi International Arts Center - Fields Sculpture Park
- Visit East Chatham
- Valatie Vacations
- Shaker Museum and Library
- Old Chatham Vacations
- Visit Valatie
- Visit Old Chatham
- Visit Kinderhook
- Niverville Vacations
- Visit Spencertown
- Visit Niverville
- Visit Stuyvesant Falls
- Car rentals near Ghent
- Car rentals near Art Omi International Arts Center - Fields Sculpture Park
- Car rentals near East Chatham
- Car rentals near Van Alen House
- Car rentals near Valatie
- Car rentals near Old Chatham
- Car rentals near Kinderhook
- Car rentals near Niverville
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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.