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Chatham Vacations from $438

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The Latest Chatham Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Sep 4 - Sep 7

    Vacation Village in the Berkshires + Flight

    Williamstown
    3 nights
    3.0 star property
    8.8/10 - Excellent (2,474 reviews)
    "It was a nice room with a beautiful location, and the pools were well maintained. However, the front desk was repeatedly grumpy whenever we had a question. Even saying good morning was met with an indifferent tone. For example, the washer didn't work (rinse cycle didn't work) and when I reported it in order to help the next person who would use it, they didn't seem interested and were put off. Additionally, the keys consistently didn't work until after several times, and whenever we tried to..."
    Reviewed July 24, 2026
    Roundtrip • Miami (MIA) - Albany (ALB)
    MIA - EWR • 1 stop EWR - MIA • 1 stop
    $551
    $438
    per traveler
    found 1 day ago
    Vacation Village in the Berkshires
  • Exterior
    Oct 1 - Oct 5

    The Cornell Inn, Lenox & The Berkshires + Flight

    Lenox
    4 nights
    3.5 star property
    9.2/10 - Wonderful (1,000 reviews)
    "The entire staff was amazing and the inn was beautiful, we will definitely be back"
    Reviewed July 21, 2026
    Roundtrip • Miami (MIA) - Albany (ALB)
    MIA - ALB • 1 stop ALB - MIA • 1 stop
    Save 100% on your flight
    $1,672
    $1,104
    per traveler
    found 1 day ago
    The Cornell Inn, Lenox & The Berkshires
  • Exterior
    Oct 1 - Oct 5

    Prospect Berkshires + Flight

    Egremont
    4 nights
    3.0 star property
    9.8/10 - Exceptional (38 reviews)
    "Loved it—unique. Great restaurant. Nice people"
    Reviewed July 25, 2026
    Roundtrip • Miami (MIA) - Albany (ALB)
    MIA - ALB • 1 stop ALB - MIA • 1 stop
    Save 100% on your flight
    $1,588
    $1,133
    per traveler
    found 1 day ago
    Prospect Berkshires
  • Seasonal outdoor pool
    Aug 28 - Sep 2

    Lodges At Cresthaven + Flight

    Lake George
    5 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
    $2,452
    $1,819
    per traveler
    found 1 day ago
    Lodges At Cresthaven
  • Exterior
    Oct 1 - Oct 5

    The Whitlock + Flight

    Lenox
    4 nights
    2.0 star property
    8.4/10 - 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, 2026
    Roundtrip • Miami (MIA) - Albany (ALB)
    MIA - ALB • 1 stop ALB - MIA • 1 stop
    $902
    $673
    per traveler
    found 1 day ago
    The Whitlock

Chatham Hotel Deals

Classic Tent, Garden View | Outdoor dining

Gatherwild Ranch

Gatherwild Ranch
3.0 star property
22.1 mi from Chatham
$200 nightly
The price is $224
Jul 30 - Jul 31
Total with taxes and fees
Gatherwild Ranch
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 $438 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.