Chatham Vacations from $709

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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.
Lake Haven Motel

Lake Haven Motel

2.5 out of 5
Price was $978, price is now $709 per person
$709
per person
Sep 20 - Sep 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
7.4/10 Good! (111 reviews)
Room was clean and staff was helpful when asked for things like toilet paper and towels. Out of their control but the whole village lost power Friday 7/3 from about 8:00 am - 2:00 pm. They don’t open their pool until 10:00 am I would have thought with the no power and heat they would have opened sooner. Only other thing is if you are on the ground floor you can definitely hear everything above you.

Reviewed on Jul 5, 2026

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Save 100% on your flight
Price was $1,363, price is now $907 per person
$907
per person
Sep 18 - Sep 21
found 12 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
9.2/10 Wonderful! (1,002 reviews)
So welcoming and peaceful. Lovely property.

Reviewed on Jul 13, 2026

Sundowner on Lake George

Sundowner on Lake George

2.5 out of 5
Save 100% on your flight
Price was $1,616, price is now $1,112 per person
$1,112
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
7.6/10 Good! (248 reviews)
Nothing like the pictures. No staffs to receive you, you have to call a phone number. The place is old and outdated.

Reviewed on May 3, 2026

Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Save 100% on your flight
Price was $1,994, price is now $1,413 per person
$1,413
per person
Sep 20 - Sep 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
9.4/10 Exceptional! (616 reviews)
what a beautiful and special place! Theres a fantastic pool for kids/family overlooking the beautiful lake. I wish we were able to stay longer. It was really one of the most beautiful places I have stayed. The Cabin lodging, the rooms, the bathrooms, everything was just great! Check out is at 10am, I wish it was maybe till noon for what you pay for but I understand because the cabins need to be cleaned. It was great!

Reviewed on Jul 9, 2026

Brook Bound Inn

Brook Bound Inn

2 out of 5
Save 100% on your flight
Price was $1,630, price is now $1,168 per person
$1,168
per person
Aug 29 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Albany (ALB)
9.2/10 Wonderful! (17 reviews)
The cabin and grounds are well-maintained. The pool was crystal clear and the slide was a nice addition. Gorgeous views!

Reviewed on Jun 28, 2026

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Stay near popular Chatham attractions

The Mac-Haydn Theatre

This intimate theater-in-the-round presents professional summer musicals with New York City talent. Every seat offers an immersive view of the dynamic performances, running from Memorial Day through Labor Day.
See properties

Chatham Hotel Deals

Country Inn & Suites by Radisson, Downtown Albany New York

Country Inn & Suites by Radisson, Downtown Albany New York

2.5 out of 5
300 Broadway Albany NY
Fully refundable
$101 nightly
The price is $116 total per night from Aug 2 to Aug 3
$116 total
Aug 2 - Aug 3
Total with taxes and fees
8.2/10 Very Good! (813 reviews)
"The room and hotel were entirely adequate. The breakfast was basic but filling. The bed was comfortable. The internet worked. We were able to park in the lot without a problem. The staff were friendly enough. Roomkeeping did a good job. Nothing too fancy, but exactly what I would expect for the very ..."

Reviewed on Jul 15, 2026

Country Inn & Suites by Radisson, Downtown Albany New York
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
$145 nightly
The price is $162 total per night from Jul 16 to Jul 17
$162 total
Jul 16 - Jul 17
Total with taxes and fees
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
$88 nightly
The price is $101 total per night from Jul 26 to Jul 27
$101 total
Jul 26 - Jul 27
Total with taxes and fees
7.8/10 Good! (1,000 reviews)
"We arrived late and left early so we didn't see too much of the property.. It was obvious that renovations were going on.. Our room was clean and comfortable. I'd stay there again."

Reviewed on Jul 12, 2026

Comfort Inn Glenmont - Albany South
See all 1,617 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 $709 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.