Chatham Vacations from $523

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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.
Gedney Farm

Gedney Farm

3.5 out of 5
Save 100% on your flight
Price was $759, price is now $523 per person
$523
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
18.4/10 Exceptional! (132 reviews)
My wife and I chose Gedney Farms at the last minute to enjoy a quick escape from the city. The staff was friendly and welcoming. The checkin and checkout experience was seamless. The room had a truly rustic charm, and clean and orderly. In the morning we took a nice walk on the grounds. For a quick and relaxing getaway, Gedney Farms is a great choice.

Reviewed on Nov 2, 2025

Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $1,723, price is now $1,026 per person
$1,026
per person
Dec 28 - Jan 2
found 1 hour ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
18.8/10 Exceptional! (13 reviews)
Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay....

Reviewed on Oct 20, 2025

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 out of 5
Save 100% on your flight
Price was $1,303, price is now $824 per person
$824
per person
Dec 28 - Jan 2
found 1 hour ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
18.4/10 Exceptional! (110 reviews)
It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!

Reviewed on Oct 27, 2025

Church Des Artistes Guest House

Church Des Artistes Guest House

3 out of 5
Roundout
Save 100% on your flight
Price was $5,233, price is now $3,586 per person
$3,586
per person
Dec 28 - Jan 2
found 1 hour ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
18.8/10 Exceptional! (18 reviews)
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Save 100% on your flight
Price was $1,615, price is now $1,153 per person
$1,153
per person
Dec 26 - Dec 30
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
14.8/10 Exceptional! (567 reviews)
Nice room, comfortable bed. This is an old grand hotel in tip top shape. We often stay in this type of hotel in NH and VT and found the Equinox to be the best maintained of them all. All the architectural class of its age in virtually new condition. Nice, reasonably priced onsite dining. We didn’t use the large indoor pool but it looked first class. Pleasant staff. We hope to return. Recommend “Ok for breakfast”, a 2nd floor breakfast & lunch restaurant downtown.

Reviewed on Oct 27, 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
$94 nightly
The price is $105 total per night from Nov 20 to Nov 21
$105 total
Nov 20 - Nov 21
Total with taxes and fees
8.6/10 Excellent! (2,135 reviews)
My room was amazing nice view of the mountains the staff were very friendly they have a beautiful indoor pool amazing hot tub and cute movie theater along with a game room and other activities

Reviewed on Nov 17, 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
$120 nightly
The price is $135 total per night from Nov 30 to Dec 1
$135 total
Nov 30 - Dec 1
Total with taxes and fees
9/10 Wonderful! (758 reviews)
The suites were large. Nice to have separate bedroom. Kitchen with all the basics. Perfect for a getaway

Reviewed on Nov 14, 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 refundableReserve now, pay when you stay
$88 nightly
The price is $99 total per night from Nov 22 to Nov 23
$99 total
Nov 22 - Nov 23
Total with taxes and fees
7.8/10 Good! (959 reviews)
Everything was amazing my bf did get a beer at the bar that was expired but everything else was amazing

Reviewed on Nov 16, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
See all 1,587 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 $523 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.