Chatham Vacations from $673
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The Latest Chatham Vacation Packages
- The Whitlock
Oct 1 - Oct 5The Whitlock + Flight
Lenox4 nights2.0 star property8.4/10 - Very Good (338 reviews)"Very nice coffee set up in the morning. Staff was super courteous and helpful. Most of property is updated although carpeting and rugs are tired. Location is great, very convenient to Tanglewood and restaurants. Parking is onsite and more than ample. B"Reviewed July 25, 2026Roundtrip • Miami (MIA) - Albany (ALB)MIA - ALB • 1 stop ALB - MIA • 1 stop$902$673found 1 day agoper traveler - The Cornell Inn, Lenox & The Berkshires
Oct 1 - Oct 5The Cornell Inn, Lenox & The Berkshires + Flight
Lenox4 nights3.5 star property9.2/10 - Wonderful (1,000 reviews)"The entire staff was amazing and the inn was beautiful, we will definitely be back"Reviewed July 21, 2026Roundtrip • Miami (MIA) - Albany (ALB)MIA - ALB • 1 stop ALB - MIA • 1 stop - Prospect Berkshires
Oct 1 - Oct 5Prospect Berkshires + Flight
Egremont4 nights3.0 star property9.8/10 - Exceptional (38 reviews)"Loved it—unique. Great restaurant. Nice people"Reviewed July 25, 2026Roundtrip • Miami (MIA) - Albany (ALB)MIA - ALB • 1 stop ALB - MIA • 1 stop - 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 - The Ponds at Foxhollow
Oct 1 - Oct 5The Ponds at Foxhollow + Flight
Lenox4 nights3.0 star property8.6/10 - Excellent (143 reviews)"This holiday apartment was very dated, dark, and had a damp smell. The pull-out sofa was extremely uncomfortable, making it impossible for anyone to get a good night’s sleep. The walls were paper-thin, so we could hear everything from our neighbors, including footsteps, and toilets flushing. As a family with a young child, we felt like we had spent three days in an assisted living facility rather than a vacation resort. The staff in the main office were friendly, but unfortunately, that is..."Reviewed July 19, 2026Roundtrip • Miami (MIA) - Albany (ALB)MIA - ALB • 1 stop ALB - MIA • 1 stop$916$728found 1 day agoper traveler
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 $673 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.