Chatham Vacations from $479

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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.
Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
Price was $542, price is now $479 per person
$479
per person
Aug 19 - Aug 21
found 6 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
8.8/10 Excellent! (1,007 reviews)
friendly helpful receptive staff, great bed and room

Reviewed on Jun 9, 2026

Bluebird Spa City Motor Lodge

Bluebird Spa City Motor Lodge

3 out of 5
Downtown Saratoga Springs
Price was $1,551, price is now $1,389 per person
$1,389
per person
Aug 28 - Aug 30
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Albany (ALB)
9/10 Wonderful! (904 reviews)
Perfect location! Step onto Broadway all the shops and restaurants within seconds.

Reviewed on Jun 7, 2026

Hyatt Place Saratoga Malta

Hyatt Place Saratoga Malta

3 out of 5
Price was $878, price is now $789 per person
$789
per person
Aug 28 - Aug 30
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Albany (ALB)
8.8/10 Excellent! (1,010 reviews)
The hotel was clean. It had two outdoor sitting areas, plus lots of indoors seating. It had a pool and exercise room which I did not have time to use. The room was bigger than expected with a sitting area and desk, plenty of counterspace, etc. All was good.

Reviewed on Jun 2, 2026

The Landing Hotel at Rivers Casino Schenectady

The Landing Hotel at Rivers Casino Schenectady

4 out of 5
Nothside
Price was $1,051, price is now $948 per person
$948
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Albany (ALB)
9.2/10 Wonderful! (1,004 reviews)
Exactly what a casino hotel should be like . Very clean and everything seems new . The staff are very friendly and attentive to our needs . We will definitely be back .

Reviewed on May 28, 2026

Marriott Albany

Marriott Albany

3.5 out of 5
Price was $602, price is now $545 per person
$545
per person
Aug 19 - Aug 21
found 6 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
8.2/10 Very Good! (1,000 reviews)
Huge hotel! Everyone was very friendly!!

Reviewed on Jun 7, 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

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
$93 nightly
The price is $106 total per night from Jun 21 to Jun 22
$106 total
Jun 21 - Jun 22
Total with taxes and fees
8/10 Very Good! (693 reviews)
"Good"

Reviewed on Jun 9, 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
$152 nightly
The price is $170 total per night from Jun 11 to Jun 12
$170 total
Jun 11 - Jun 12
Total with taxes and fees
9/10 Wonderful! (971 reviews)
"rented for 2 nights. Apt was clean and climate control worked as expected. Nicely equipped location is good."

Reviewed on Jun 9, 2026

Berkshire Mountain Lodge
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
$136 nightly
The price is $152 total per night from Jun 14 to Jun 15
$152 total
Jun 14 - Jun 15
Total with taxes and fees
8.8/10 Excellent! (2,392 reviews)
"This is a big beautful modern condo complex about 20 mins outside Wiilamstown (to the north) or Pittsfield (to the south). Huge swimming pools - one indoors, one out. Beautiful views of the Berkshires. Quiet rural environment. I could hear the frogs singing and the cricketa chirp at night. Excellent ..."

Reviewed on Jun 8, 2026

Vacation Village in the Berkshires
See all 1,632 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 $479 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.