Chatham Vacations from $483

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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 Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Nothside
Price was $625, price is now $483 per person
$483
per person
May 8 - May 11
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
9.2/10 Wonderful! (1,001 reviews)
The staff couldn’t have been nicer. The facility was clean and in great condition.

Reviewed on Mar 9, 2026

DoubleTree by Hilton Schenectady Downtown

DoubleTree by Hilton Schenectady Downtown

4 out of 5
Downtown
Price was $987, price is now $833 per person
$833
per person
May 14 - May 19
found 1 hour ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
8.4/10 Very Good! (744 reviews)
Quick check in and out. Bar is open late, quiet

Reviewed on Mar 4, 2026

Hilton Garden Inn Albany Airport

Hilton Garden Inn Albany Airport

3 out of 5
Price was $590, price is now $518 per person
$518
per person
Apr 24 - Apr 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
8.2/10 Very Good! (1,315 reviews)
There were two employees that obviously hated working the night shift. Otherwise the others were gold!!

Reviewed on Mar 8, 2026

Marriott Albany

Marriott Albany

3.5 out of 5
Price was $737, price is now $649 per person
$649
per person
May 3 - May 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
8.4/10 Very Good! (878 reviews)
Everything was fine except for the bedding. All the pillows smelled like body odor bad. I can’t figure out how the cleaner didn’t smell them when changing the bedding. I didn’t use them and their systems were down soo their phone wasn’t working to call the desk. Everything else was fine.

Reviewed on Mar 10, 2026

Hilton Albany

Hilton Albany

3.5 out of 5
Downtown Albany
Price was $797, price is now $702 per person
$702
per person
May 3 - May 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
7/10 Good! (1,010 reviews)
The hotel was clean and the staff was friendly. Unfortunately the heating/AC system in our room was extremely loud and would turn on with banging and grinding noises and kept us up during the night.

Reviewed on Mar 8, 2026

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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.

The Mac-Haydn Theatre

Chatham Hotel Deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $141 total per night from Mar 22 to Mar 23
$141 total
Mar 22 - Mar 23
Total with taxes and fees
8.8/10 Excellent! (2,295 reviews)
Great place in Williamstown. Near ski resort.

Reviewed on Mar 9, 2026

Vacation Village in the Berkshires
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2 out of 5
282 Cairo Junction Rd Catskill NY
$141 nightly
The price is $152 total per night from Mar 16 to Mar 17
$152 total
Mar 16 - Mar 17
Total with taxes and fees
9.6/10 Exceptional! (171 reviews)
A very cozy cabin! We loved how spread out they were and had privacy and quiet. Beautiful view! Well equipped for cooking/grilling dinner and simple breakfasts. Could use a good deep clean. I understand it’s glamping but the built up dust in spots and the vents was a little gross.

Reviewed on Mar 10, 2026

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Country Inn & Suites by Radisson, Downtown Albany New York

Country Inn & Suites by Radisson, Downtown Albany New York

3 out of 5
300 Broadway Albany NY
Fully refundable
$124 nightly
The price is $141 total per night from Apr 9 to Apr 10
$141 total
Apr 9 - Apr 10
Total with taxes and fees
8/10 Very Good! (533 reviews)
The staff is always friendly and very helpful! Very comfortable stay, and walking distance to downtown. They also offer free parking which is a huge plus downtown! This is my second work trip to downtown Albany and have stayed here both times. Breakfast is also decent, full, hot breakfast. I definitely ...

Reviewed on Mar 10, 2026

Country Inn & Suites by Radisson, Downtown Albany New York
See all 1,603 properties in Chatham
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 $483 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.