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Chatham Vacations from $630

Book a Hotel + Flight or Car together to unlock savings

The Latest Chatham Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Balcony
    Sep 4 - Sep 8

    Studio 6 Lake George, NY - Adirondacks + Flight

    Lake George
    4 nights
    2.0 star property
    9.4/10 - Exceptional (6 reviews)
    "Friendly staff, nearby shops, great location."
    Reviewed July 23, 2026
    Roundtrip • New York (EWR) - Albany (ALB)
    EWR - ALB • 1 stop ALB - EWR • 1 stop
    $906
    $630
    per traveler
    found 3 hours ago
    Studio 6 Lake George, NY - Adirondacks
  • Seasonal outdoor pool
    Sep 4 - Sep 8

    Lodges At Cresthaven + Flight

    Lake George
    4 nights
    4.0 star property
    9.4/10 - Exceptional (621 reviews)
    Roundtrip • New York (EWR) - Albany (ALB)
    EWR - ALB • 1 stop ALB - EWR • 1 stop
    Save 100% on your flight
    $2,341
    $1,490
    per traveler
    found 3 hours ago
    Lodges At Cresthaven
  • Private beach, kayaking, rowing
    Sep 4 - Sep 8

    Sundowner on Lake George + Flight

    Lake George
    4 nights
    2.5 star property
    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 The place is old and outdated."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 May 3, 2026
    Roundtrip • New York (EWR) - Albany (ALB)
    EWR - ALB • 1 stop ALB - EWR • 1 stop
    Save 100% on your flight
    $1,435
    $1,012
    per traveler
    found 3 hours ago
    Sundowner on Lake George
  • Exterior
    Sep 16 - Sep 21

    The Cornell Inn, Lenox & The Berkshires + Flight

    Lenox
    5 nights
    3.5 star property
    9.2/10 - Wonderful (1,000 reviews)
    Roundtrip • Dallas (DFW) - Albany (ALB)
    DAL - ALB • 1 stop ALB - DAL • 1 stop
    Save 100% on your flight
    $1,801
    $1,317
    per traveler
    found 7 hours ago
    The Cornell Inn, Lenox & The Berkshires
  • Front of property - evening/night
    Sep 16 - Sep 21

    The Ponds at Foxhollow + Flight

    Lenox
    5 nights
    3.0 star property
    8.6/10 - 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, 2026
    Roundtrip • Dallas (DFW) - Albany (ALB)
    DAL - ALB • 1 stop ALB - DAL • 1 stop
    $1,303
    $1,008
    per traveler
    found 7 hours ago
    The Ponds at Foxhollow

Chatham Hotel Deals

Balcony

Chatham Travel Lodge

Chatham Travel Lodge
2.5 star property
2.6 mi from Chatham
7.8 out of 10, Good, (233 reviews)
"Very nice"
$112 nightly
The price is $125
Aug 2 - Aug 3
Total with taxes and fees
Chatham Travel Lodge
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.
See all properties in Chatham

Frequently Asked Questions

How much does a Chatham vacation package cost?

You'll find cheap prices from $630 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.