Chatham Vacations from $416
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Chatham Vacation Packages
- Vacation Village in the Berkshires
Sep 17 - Sep 20Vacation Village in the Berkshires + Flight
Williamstown3 nights3.0 star property8.8/10 - Excellent (2,480 reviews)"This place was awesome!!!! The staff was so nice. The location is beautiful, and it's super easy to drive to fun attractions. I honestly wish I could have stayed longer!"Reviewed July 27, 2026Roundtrip • Orlando (MCO) - Albany (ALB)MCO - ALB • 1 stop ALB - MCO • 1 stop$531$416found 1 day agoper traveler - The Perch Hotel
Sep 3 - Sep 7The Perch Hotel + Flight
East Windham4 nights2.0 star property9.6/10 - Exceptional (33 reviews)"It was a wonderful stay the room was very clean and spacious. The common area downstairs was my favorite part of my whole stay. Wide variety of games to play with other guest that are also staying."Reviewed July 16, 2026Roundtrip • Atlanta (ATL) - Albany (ALB)ATL - ALB • Nonstop ALB - ATL • Nonstop - Brook Bound Inn
Sep 17 - Sep 20Brook Bound Inn + Flight
Wilmington3 nights2.0 star property9.2/10 - 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 June 28, 2026Roundtrip • Orlando (MCO) - Albany (ALB)MCO - ALB • 1 stop ALB - MCO • 1 stop$866$632found 1 day agoper traveler - Lake Haven Motel
Sep 20 - Sep 26Lake Haven Motel + Flight
Lake George6 nights2.5 star property7.4/10 - Good (112 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 July 5, 2026Roundtrip • New York (NYC) - Albany (ALB)LGA - ALB • Nonstop ALB - LGA • Nonstop - Lodges At Cresthaven
Aug 28 - Sep 2Lodges At Cresthaven + Flight
Lake George5 nights4.0 star property9.4/10 - Exceptional (621 reviews)Roundtrip • New York (EWR) - Albany (ALB)EWR - ALB • 1 stop ALB - EWR • 1 stop
Chatham Hotel Deals
Holiday Inn Express Hotel & Suites West Coxsackie by IHG
Holiday Inn Express Hotel & Suites West Coxsackie by IHG
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
Comfort Inn & Suites East Greenbush - Albany
Comfort Inn & Suites East Greenbush - AlbanyFrequently Asked Questions
How much does a Chatham vacation package cost?
You'll find cheap prices from $416 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.