Chatham Vacations from $542
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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.
Albany Airport Inn
$542
per person
Dec 2 - Dec 8
found 16 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Albany (ALB)
6.6/10 (1,013 reviews)
This hotel has become my home away from home. I feel like I've stayed in almost half of the rooms on the property at least once a piece. The rooms are always clean and neat, as is the entire hotel. The pool is well maintained and the staff is impeccable and very good at their jobs!
Reviewed on Sep 16, 2026
Aspen At Manchester
$575
per person
Oct 23 - Oct 28
found 19 hours ago
Roundtrip non-stop flight included
Raleigh (RDU) to Albany (ALB)
8.8/10 Excellent! (683 reviews)
Absolutely loved this property! Amazing location, super clean and spacious rooms! We loved being in close proximity to the town, which was soooooo amazingly pet friendly! We will definitely be back
Reviewed on Sep 14, 2026
Saratoga Casino Hotel
$576
per person
Oct 23 - Oct 26
found 3 hours ago
Roundtrip flight included
St. Petersburg (PIE) to Albany (ALB)
9.4/10 Exceptional! (1,004 reviews)
I loved saratoga casino hotel. Everyone was so helpful. I come here several times a year and can't say enough about the wonderful service. Everyone is so pleasant ☺️ and helpful.
Reviewed on Sep 16, 2026
The Manchester View
$633
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Albany (ALB)
9.4/10 Exceptional! (875 reviews)
Great place. Exceeded our expectations. The view, and surroundings are spectacular. And the "continental" breakfast was beyond continental. And it's dog friendly!!!
Reviewed on Sep 15, 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
Country Inn & Suites by Radisson, Downtown Albany New York
300 Broadway Albany NY
Fully refundable
$110 nightly
$126 total
Sep 27 - Sep 28
Total with taxes and fees
8.2/10 Very Good! (1,073 reviews)
"Easy acccess off route 90 with free breakfast & free parking. Mattress was excellent! Room very clean"
Reviewed on Sep 15, 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
$122 nightly
$136 total
Sep 17 - Sep 18
Total with taxes and fees
8.8/10 Excellent! (2,647 reviews)
"There was mold in the outdoor pool. There wasn’t an elevator."
Reviewed on Sep 16, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$111 nightly
$124 total
Oct 1 - Oct 2
Total with taxes and fees
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 $542 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.
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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.
