Chatham Vacations from $396

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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.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
per person
Aug 15 - Aug 18
found 18 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.8/10 Excellent! (493 reviews)
Clean, comfortable and great staff. Highly recommend and will be staying there again in the future.

Reviewed on Jul 10, 2025

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Save 100% on your flight
per person
Aug 15 - Aug 18
found 18 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
9/10 Wonderful! (1,000 reviews)
Cornell Inn was lovely. The place is so clean- and I’m a germaphobe! The staff was kind, helpful and welcoming. The breakfast was delicious and served outside in a beautiful garden. Would definitely recommend.

Reviewed on Jul 7, 2025

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 out of 5
Save 100% on your flight
per person
Aug 15 - Aug 18
found 18 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
9.2/10 Wonderful! (1,002 reviews)
Air conditioner was loud, went on and off frequently. Disturbed sleep

Reviewed on Jul 7, 2025

Sundowner on Lake George

Sundowner on Lake George

2.5 out of 5
per person
Aug 15 - Aug 18
found 20 hours ago
Roundtrip non-stop flight included
Raleigh (RDU) to Albany (ALB)
7.4/10 Good! (236 reviews)
Overpriced for what it is and given many other options. Totally expected a view and barely one of you stated outside at edge of deck. Bed pillows were ridiculously uncomfortable /Get many small pillows for flexibility.

Reviewed on Oct 12, 2024

Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
per person
Aug 21 - Aug 24
found 24 hours ago
Roundtrip flight included
Billings (BIL) to Albany (ALB)
9.2/10 Wonderful! (34 reviews)
Had an excellent stay at the brand new Brookmere Hotel. The room was clean and comfortable, and the service throughout was top-notch. I want to give a special shoutout to Jose from the restaurant staff, who helped me with a personal request. His kindness and professionalism really stood out. Great hospitality all around — highly recommend!

Reviewed on Jul 8, 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
$103 nightly
The price is $115 total per night from Jul 13 to Jul 14
$115 total
Jul 13 - Jul 14
Total includes taxes and fees
8.6/10 Excellent! (1,860 reviews)
"Activities look good during week but we miss them on our weekend stay"

Reviewed on Jul 8, 2025

Vacation Village in the Berkshires
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $141 total per night from Jul 15 to Jul 16
$141 total
Jul 15 - Jul 16
Total includes taxes and fees
8.4/10 Very Good! (1,008 reviews)
"Great stay"

Reviewed on Jul 5, 2025

Best Western Plus Berkshire Hills Inn & Suites
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 out of 5
190 Meadow Street, South Lee, MA
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $170 total per night from Jul 16 to Jul 17
$170 total
Jul 16 - Jul 17
Total includes taxes and fees
9/10 Wonderful! (667 reviews)
"Very good"

Reviewed on Jul 7, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
See all 1,598 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 $396 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.