Chatham Vacations from $398

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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

Albany Airport Inn

2.5 out of 5
Price was $480, price is now $398 per person
$398
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Albany (ALB)
6.6/10 (1,006 reviews)

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $815, price is now $534 per person
$534
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Albany (ALB)
9.2/10 Wonderful! (1,004 reviews)

Hideaway Inn Lenox

Hideaway Inn Lenox

2 out of 5
Price was $694, price is now $497 per person
$497
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Albany (ALB)
8/10 Very Good! (64 reviews)

The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
Price was $621, price is now $453 per person
$453
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Albany (ALB)
8.4/10 Very Good! (156 reviews)
liked it was clean . furniture is dated. Roads need repair . too many potholes

Reviewed on Nov 2, 2026

Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views

Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views

3 out of 5
Price was $899, price is now $759 per person
$759
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
10/10 Exceptional! (1 review)
Wonderful

Reviewed on Mar 29, 2026

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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.
See properties

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
$128 nightly
The price is $143 total per night from Nov 5 to Nov 6
$143 total
Nov 5 - Nov 6
Total with taxes and fees
Vacation Village in the Berkshires
Country Inn & Suites by Radisson, Downtown Albany New York

Country Inn & Suites by Radisson, Downtown Albany New York

2.5 out of 5
300 Broadway Albany NY
Fully refundable
$101 nightly
The price is $116 total per night from Nov 22 to Nov 23
$116 total
Nov 22 - Nov 23
Total with taxes and fees
8.2/10 Very Good! (1,234 reviews)
"Price is good for the area. The surrounding area isn’t great, located near a bus depot and abandoned factory building. Free parking is a plus. 3rd floor seems to have an issue with their heat/ ac system not working. We checked into the first room and it was 77 degrees in the room and would not go ..."

Reviewed on Nov 4, 2026

Country Inn & Suites by Radisson, Downtown Albany New York
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $128 total per night from Dec 5 to Dec 6
$128 total
Dec 5 - Dec 6
Total with taxes and fees
Berkshire Mountain Lodge
See all 1,622 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 $398 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.