Chatham Vacations from $559

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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.
Aspen At Manchester

Aspen At Manchester

2.5 out of 5
Price was $663, price is now $559 per person
$559
per person
Dec 16 - Dec 20
found 19 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.8/10 Excellent! (709 reviews)

Hotel Kinsley

Hotel Kinsley

3.5 out of 5
Stockade District
Save 100% on your flight
Price was $1,580, price is now $1,220 per person
$1,220
per person
Dec 27 - Jan 2
found 14 hours ago
Roundtrip flight included
San Juan (SJU) to Albany (ALB)
9/10 Wonderful! (405 reviews)

Luxury Private Estate w Pool Near Rhinebeck

Luxury Private Estate w Pool Near Rhinebeck

2 out of 5
Save 100% on your flight
Price was $11,705, price is now $9,710 per person
$9,710
per person
Dec 27 - Jan 2
found 14 hours ago
Roundtrip flight included
San Juan (SJU) to Albany (ALB)
No reviews

Kingston Carriage House

Kingston Carriage House

4 out of 5
Rondout
Price was $1,460, price is now $1,232 per person
$1,232
per person
Dec 27 - Jan 2
found 14 hours ago
Roundtrip flight included
San Juan (SJU) to Albany (ALB)
9.2/10 Wonderful! (57 reviews)

The Landing Hotel at Rivers Casino Schenectady

The Landing Hotel at Rivers Casino Schenectady

4 out of 5
Nothside
Price was $1,085, price is now $919 per person
$919
per person
Dec 16 - Dec 22
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
9.2/10 Wonderful! (1,005 reviews)

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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
$108 nightly
The price is $121 total per night from Nov 16 to Nov 17
$121 total
Nov 16 - Nov 17
Total with taxes and fees
8.8/10 Excellent! (2,853 reviews)
"Big place,nice indoor pool with arcade. Fireplace in the suite and nice balcony on 2nd floor units. Really close to Jimney Peak"

Reviewed on Nov 15, 2026

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
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
$107 nightly
The price is $119 total per night from Dec 16 to Dec 17
$119 total
Dec 16 - Dec 17
Total with taxes and fees
Berkshire Mountain Lodge
See all 1,605 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 $559 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.