Chatham Vacations from $349

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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.
Four Points by Sheraton Albany

Four Points by Sheraton Albany

3 out of 5
Price was $425, price is now $349 per person
$349
per person
Dec 30 - Jan 2
found 3 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
9/10 Wonderful! (525 reviews)
Thank you for the late check out.

Reviewed on Oct 14, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Price was $1,280, price is now $964 per person
$964
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
7.4/10 Good! (549 reviews)
The breakfast staff were cold.

Reviewed on Oct 19, 2025

Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $1,261, price is now $951 per person
$951
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
9.6/10 Exceptional! (11 reviews)
Great property. Amazing views!

Reviewed on Dec 2, 2024

The Clocktower Hotel at Century House, an Ascend Collection Hotel

The Clocktower Hotel at Century House, an Ascend Collection Hotel

2.5 out of 5
Price was $500, price is now $393 per person
$393
per person
Dec 5 - Dec 8
found 18 hours ago
Roundtrip flight included
Charlotte (CLT) to Albany (ALB)
8.4/10 Very Good! (1,022 reviews)
Property was clean & neat. Room was clean & smelled nice.

Reviewed on Oct 20, 2025

Marriott Albany

Marriott Albany

3.5 out of 5
Price was $540, price is now $456 per person
$456
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.2/10 Very Good! (724 reviews)
Nice facility. They're not preference anytime I visit Albany.

Reviewed on Oct 19, 2025

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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
$112 nightly
The price is $125 total per night from Oct 30 to Oct 31
$125 total
Oct 30 - Oct 31
Total with taxes and fees
8.6/10 Excellent! (2,079 reviews)
"Front desk was friendly and helpful. Plenty of parking near our specific unit. Our room was clean, spacious, and very comfortable. The pool and hot tub area were clean and had plenty of towels to use. This was our first time here and we will definitely come back."

Reviewed on Oct 19, 2025

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $126 total per night from Nov 2 to Nov 3
$126 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (716 reviews)
"Yes, everything was very well set up. Thanks."

Reviewed on Oct 19, 2025

Berkshire Mountain Lodge
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
Fully refundable
$103 nightly
The price is $115 total per night from Nov 2 to Nov 3
$115 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (908 reviews)
"Enjoyed dinner and drinks"

Reviewed on Oct 18, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
See all 1,588 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.

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 $349 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.