Chatham Vacations from $545

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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.
The Dewey

The Dewey

3.5 out of 5
Price was $716, price is now $545 per person
$545
per person
Apr 8 - Apr 11
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
8.6/10 Excellent! (329 reviews)
Great spot. Lots of history.

Reviewed on Sep 12, 2025

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

2 out of 5
Price was $888, price is now $579 per person
$579
per person
Mar 16 - Mar 20
found 2 days ago
Roundtrip non-stop flight included
Fayetteville (XNA) to Albany (ALB)
7.6/10 Good! (558 reviews)
Excellent location!!

Reviewed on Dec 26, 2025

Prospect Berkshires

Prospect Berkshires

3 out of 5
Price was $1,063, price is now $718 per person
$718
per person
Apr 8 - Apr 11
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
9.4/10 Exceptional! (13 reviews)
Wow, just wow! My high school friend and I met up at Prospect Berkshires for a girls weekend. We had an incredible time relaxing by using all the amenities. The staff are so helpful and profession.

Reviewed on Nov 29, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Manchester Village Historic District
Save 100% on your flight
Price was $2,412, price is now $1,774 per person
$1,774
per person
Feb 13 - Feb 17
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Albany (ALB)
7.4/10 Good! (567 reviews)
Was surprised at the dirty floors in common area and in my room one of the curtain sheers was ripped, other curtains were hanging off hokks, caulking at sink looked old, cracked, carpets in staircase dirty. I fear this beautiful hotel is in a downward spiral. One front desk person directed me to closed restaurants...

Reviewed on Jan 9, 2026

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $830, price is now $627 per person
$627
per person
Apr 8 - Apr 11
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
9/10 Wonderful! (1,002 reviews)
The staff was very welcoming and attentive. Room was clean.

Reviewed on Jan 3, 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

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
$126 nightly
The price is $141 total per night from Jan 19 to Jan 20
$141 total
Jan 19 - Jan 20
Total with taxes and fees
8.6/10 Excellent! (2,202 reviews)
Clean rooms, chimney did not work

Reviewed on Jan 4, 2026

Vacation Village in the Berkshires
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2 out of 5
282 Cairo Junction Rd Catskill NY
$169 nightly
The price is $183 total per night from Jan 15 to Jan 16
$183 total
Jan 15 - Jan 16
Total with taxes and fees
9.4/10 Exceptional! (119 reviews)
I loved every single part of the stay

Reviewed on Jan 8, 2026

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Comfort Inn Glenmont - Albany South

Comfort Inn Glenmont - Albany South

2.5 out of 5
37 Route 9W Glenmont NY
Fully refundable
$81 nightly
The price is $93 total per night from Jan 25 to Jan 26
$93 total
Jan 25 - Jan 26
Total with taxes and fees
7.8/10 Good! (1,001 reviews)
Clean room, comfortable bed

Reviewed on Jan 4, 2026

Comfort Inn Glenmont - Albany South
See all 1,584 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 $545 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.