Chatham Vacations from $462

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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.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $579, price is now $462 per person
$462
per person
Aug 17 - Aug 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
8.8/10 Excellent! (2,411 reviews)
The "2 bedroom oom suite" was 2 condos -- one with a full kitchen and the other with a kitchenette. Worked very well for a couple and 2 adult children. Pools, both indoor and outdoor were very nice, and free gas grill was great for a barbecue. Overall, lovely for our July 4th get away

Reviewed on Jul 7, 2026

Wilburton Inn

Wilburton Inn

3.5 out of 5
Price was $1,597, price is now $1,183 per person
$1,183
per person
Aug 23 - Aug 28
found 9 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
9/10 Wonderful! (130 reviews)
This is a magical place. We enjoyed a very relaxing four days at the Wilburton. First time, we will be back!

Reviewed on Mar 21, 2026

Aspen At Manchester

Aspen At Manchester

2.5 out of 5
Price was $1,079, price is now $817 per person
$817
per person
Aug 23 - Aug 28
found 9 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
8.8/10 Excellent! (667 reviews)
Clean..convenient location. Only complaint is AC going on and off constantly throughout the night..noisier than normal.

Reviewed on Jun 22, 2026

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Price was $618, price is now $485 per person
$485
per person
Aug 8 - Aug 11
found 16 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
9/10 Wonderful! (1,009 reviews)
Nice property good coffee

Reviewed on Jul 6, 2026

Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $860, price is now $678 per person
$678
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Albany (ALB)
9.2/10 Wonderful! (17 reviews)
The cabin and grounds are well-maintained. The pool was crystal clear and the slide was a nice addition. Gorgeous views!

Reviewed on Jun 28, 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

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
$101 nightly
The price is $115 total per night from Aug 2 to Aug 3
$115 total
Aug 2 - Aug 3
Total with taxes and fees
8/10 Very Good! (786 reviews)
"Not good"

Reviewed on Jul 7, 2026

Country Inn & Suites by Radisson, Downtown Albany New York
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
$143 nightly
The price is $159 total per night from Jul 12 to Jul 13
$159 total
Jul 12 - Jul 13
Total with taxes and fees
8.8/10 Excellent! (2,426 reviews)
"The "2 bedroom oom suite" was 2 condos -- one with a full kitchen and the other with a kitchenette. Worked very well for a couple and 2 adult children. Pools, both indoor and outdoor were very nice, and free gas grill was great for a barbecue. Overall, lovely for our July 4th get away"

Reviewed on Jul 7, 2026

Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $169 total per night from Jul 9 to Jul 10
$169 total
Jul 9 - Jul 10
Total with taxes and fees
9.2/10 Wonderful! (1,007 reviews)
"Great location with easy parking Excellent cleaning staff. Done promptly and right. Very helpful front desk staff."

Reviewed on Jul 7, 2026

The Yankee Inn
See all 1,623 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 $462 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.