Chatham Vacations from $581
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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.
Vacation Village in the Berkshires
$581
per person
Oct 23 - Oct 29
found 1 day ago
Roundtrip flight included
Chicago (MDW) to Albany (ALB)
8.8/10 Excellent! (2,503 reviews)
This is a great resort with large, clean, well equipped rooms. My only gripe is the location is quite remote and you have to drive 10 minutes for food.
Reviewed on Aug 18, 2026
Stay near popular Chatham attractions
The Mac-Haydn Theatre
This intimate theater-in-the-round presents professional summer musicals with New York City talent. Every seat offers an immersive view of the dynamic performances, running from Memorial Day through Labor Day.
Chatham Hotel Deals
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
$128 nightly
$143 total
Aug 31 - Sep 1
Total with taxes and fees
8.8/10 Excellent! (2,549 reviews)
"This is a great resort with large, clean, well equipped rooms. My only gripe is the location is quite remote and you have to drive 10 minutes for food."
Reviewed on Aug 18, 2026
Country Inn & Suites by Radisson, Downtown Albany New York
300 Broadway Albany NY
Fully refundable
$105 nightly
$120 total
Aug 30 - Aug 31
Total with taxes and fees
8.2/10 Very Good! (970 reviews)
"Nice place to stay. It is not dog friendly as i found out the next morning after my 2am check in. They did make accommodations so that was appreciated."
Reviewed on Aug 19, 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$158 nightly
$176 total
Sep 14 - Sep 15
Total with taxes and fees
9.2/10 Wonderful! (1,009 reviews)
"No elevators to the second floor. Breakfast was terrible. Staff was good. The ice machine was only in the main building no satellite machines. Furniture needs upgrades. Air conditioning needs upgrades."
Reviewed on Aug 18, 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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Frequently asked questions
How much does a Chatham vacation package cost?
You'll find cheap prices from $581 on Expedia for your Chatham getaway. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Chatham costs.
What are the cheapest months to go to Chatham?
If you'd like to snag a cheap Chatham vacation package, consider traveling in June, September and October. You'll typically find better rates on flights and hotels during these months — ideal for travelers wishing to save money.
How many days is enough for Chatham?
The ideal length for your Chatham vacation depends on what you'd like to see and do. Typically, a few days to a week will give you time to check out all the top attractions and discover some hidden gems along the way.
How to find the best Chatham package deals?
Begin your search for a Chatham package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select some filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Chatham package deal straight away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Chatham escape underway.
Is it cheaper to book a Chatham vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking accommodations and flights separately. Better still, you can tailor your Chatham escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Chatham?
Secure incredible bargains by reserving your flights ahead of time with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for an impromptu Chatham escape.
Does Expedia offer Book Now, Pay Later Chatham vacation packages?
If you're anything like us, you love exploring new places but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Chatham trip over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.
Explore a world of travel with Expedia
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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.
