Chatham Vacations from $559

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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 Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Nothside
Price was $755, price is now $559 per person
$559
per person
Apr 20 - Apr 24
found 24 hours ago
Roundtrip flight included
Charlotte (CLT) to Albany (ALB)
9.2/10 Wonderful! (1,001 reviews)
Shower was cold. No shower door or curtain to close to keep the heat in the shower. All the movies in the guide stated, unavailable! No coffee pot. Great warm cookie provided upon arrival. Staff very friendly. Room was clean and comfortable.

Reviewed on Mar 2, 2026

The Wiltwyck

The Wiltwyck

3.5 out of 5
Price was $725, price is now $583 per person
$583
per person
May 18 - May 22
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
9.4/10 Exceptional! (173 reviews)
It was an OK Inn. I felt it was overpriced.

Reviewed on Jan 29, 2026

Hotel Kinsley

Hotel Kinsley

3.5 out of 5
Stockade District
Price was $903, price is now $746 per person
$746
per person
May 18 - May 22
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
9/10 Wonderful! (344 reviews)
Very clean room and bathroom. Nice vibe. S

Reviewed on Feb 24, 2026

Marriott Albany

Marriott Albany

3.5 out of 5
Price was $1,196, price is now $1,003 per person
$1,003
per person
Apr 13 - Apr 17
found 24 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Albany (ALB)
8.4/10 Very Good! (870 reviews)
Room was VERY far from the parking garage. There was no internet or streaming available so the front desk asked if I wanted to cancel. I didn't, but was surprised they didn't offer a free pastry or muffin with their morning coffee(4 .00 dollars) as a trade. Especially since most places have these for FREE!! lol. Walk from garage to room was way too far. Will not stay again due to this.

Reviewed on Mar 5, 2026

Hutton Brickyards Riverfront Hotel + Venue

Hutton Brickyards Riverfront Hotel + Venue

3.5 out of 5
Price was $968, price is now $827 per person
$827
per person
May 18 - May 22
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.8/10 Excellent! (103 reviews)
Everything was perfect

Reviewed on Feb 17, 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
$119 nightly
The price is $133 total per night from Mar 8 to Mar 9
$133 total
Mar 8 - Mar 9
Total with taxes and fees
8.8/10 Excellent! (2,283 reviews)
Looks way better in person than the pictures. Still old and dated but not as spooky as the pictures seem. They don't tell you this at all, just expect you to read a packet - there is no housekeeping, no nothing. You are supposed to take your own trash out. They also do not really clean the room beforehand ...

Reviewed on Mar 7, 2026

Vacation Village in the Berkshires
Comfort Inn Glenmont - Albany South

Comfort Inn Glenmont - Albany South

2.5 out of 5
37 Route 9W Glenmont NY
Fully refundable
$82 nightly
The price is $94 total per night from Mar 19 to Mar 20
$94 total
Mar 19 - Mar 20
Total with taxes and fees
7.8/10 Good! (1,007 reviews)
The room was nice. They don't have any dressers for you to put your clothes in. The gym is extremely lack luster. It doesn't have any weights. Just 3 machines. The pool area

Reviewed on Mar 2, 2026

Comfort Inn Glenmont - Albany South
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
$149 nightly
The price is $161 total per night from Mar 11 to Mar 12
$161 total
Mar 11 - Mar 12
Total with taxes and fees
9.6/10 Exceptional! (167 reviews)
Clean room

Reviewed on Mar 6, 2026

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
See all 1,603 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 $559 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.