Chatham Vacations from $311

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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
Price was $432, price is now $311 per person
$311
per person
Jun 19 - Jun 22
found 15 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
9/10 Wonderful! (928 reviews)
Nice for families, has kitchen facilities for cooking. Door to room needs attention. Had to slam hard to close. Nice big bathroom. Thought we were getting 2 beds but had king bed and pull out couch. Wouldn’t always work for everyone. Could hear dog barking in nearby room. Price was right

Reviewed on May 17, 2026

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
Save 100% on your flight
Price was $650, price is now $457 per person
$457
per person
Jun 19 - Jun 22
found 15 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
9.2/10 Wonderful! (894 reviews)
Family friendly resort with amenities the whole family can enjoy!

Reviewed on May 12, 2026

The Yankee Inn

The Yankee Inn

2.5 out of 5
Price was $1,061, price is now $753 per person
$753
per person
Jul 30 - Aug 4
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Albany (ALB)
9.2/10 Wonderful! (1,007 reviews)
Breakfast ok, coffee good, staff great

Reviewed on May 19, 2026

Gedney Farm

Gedney Farm

3.5 out of 5
Price was $921, price is now $666 per person
$666
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Albany (ALB)
9.4/10 Exceptional! (136 reviews)
Had a great stay. Beautiful location.

Reviewed on May 15, 2026

Hideaway Inn Lenox

Hideaway Inn Lenox

2 out of 5
Price was $766, price is now $578 per person
$578
per person
Jun 30 - Jul 3
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
6/10 (1 review)
The room was comfortable and well done. There was no heat in our room with no control for the air unit. There was also a drip coming from the exhaust fan in the bathroom. We were only there one night so I didn't call for support.

Reviewed on Apr 16, 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

Comfort Inn Glenmont - Albany South

Comfort Inn Glenmont - Albany South

2.5 out of 5
37 Route 9W Glenmont NY
Fully refundable
$93 nightly
The price is $107 total per night from May 31 to Jun 1
$107 total
May 31 - Jun 1
Total with taxes and fees
7.8/10 Good! (1,000 reviews)
"Room was great. Other areas were under construction so hard to say. Landscaping/entrance could be nicer. Staff was lovely and location is super convenient for downtown."

Reviewed on May 18, 2026

Comfort Inn Glenmont - Albany South
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $126 total per night from May 24 to May 25
$126 total
May 24 - May 25
Total with taxes and fees
9/10 Wonderful! (941 reviews)
"the Kitchen appeared to be fully equiped. The only cpmplaint I have was there were no avaiable plugs for mt CPAP machine nect to the bed> Easy fix is to offit the room with a multi plug on the night table.or lamp with plugs. Also there were no USB charging ports. Otherwise the facility was great"

Reviewed on May 19, 2026

Berkshire Mountain Lodge
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
$114 nightly
The price is $130 total per night from May 31 to Jun 1
$130 total
May 31 - Jun 1
Total with taxes and fees
8/10 Very Good! (646 reviews)
"The breakfast is ok. No meat only eggs. The harshbrown tastes like overweight."

Reviewed on May 19, 2026

Country Inn & Suites by Radisson, Downtown Albany New York
See all 1,642 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 $311 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.