Chatham Vacations

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Find the Best Chatham Vacation Packages

Chatham Hotel Deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is ₩149,867 per night from Aug 27 to Aug 28
₩149,867
₩182,580 total
Aug 27 - Aug 28
includes taxes & fees
8.6/10 Excellent! (1,957 reviews)
"A rare, affordable place in the Berkshires! The scenery is stunning, and we loved the pools (both indoor and out) and fire pit. The staff was friendly, and our room was spacious but dated: the blinds were broken, the doors stuck, the walls were paper thin and our king-size mattress had clearly seen ..."

Reviewed on Aug 18, 2025

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is ₩106,197 per night from Sep 7 to Sep 8
₩106,197
₩149,532 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (586 reviews)
"I stayed here for a work trip to a remote project site. This place was very impressive for the money. The rooms were large and had everything. The place was clean and staff very pleasant and accommodating. I didn’t expect a lot for what I paid but was pleasantly surprised."

Reviewed on Aug 23, 2025

Berkshire Mountain Lodge
Four Points by Sheraton Albany

Four Points by Sheraton Albany

3 out of 5
3 Mount Hope Way, Albany, NY
Fully refundableReserve now, pay when you stay
The price is ₩185,400 per night from Sep 1 to Sep 2
₩185,400
₩212,283 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (488 reviews)
"Very nice rooms"

Reviewed on Aug 18, 2025

Four Points by Sheraton Albany
See all 1,593 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.

Frequently asked questions

How much does a Chatham vacation package cost?
You'll find cheap prices 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?
The off-season is the best time to visit Chatham if you're trying to save. Another tip for getting cheap Chatham vacation packages? Try to avoid visiting during public holidays and any major events or festivals.
How many days is enough for Chatham?
The ideal duration for your Chatham vacation depends on what you'd like to see and do. Usually, a few days to a week will give you enough time to go to all the top sights 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.
How to plan a trip to Chatham?

  1. Pick your dates: What you'd like to do in Chatham and your favorite season will help you decide when to get away.
  2. Plan your budget wisely: Besides the price of your hotel, you'll need to factor in other expenses. These include flights, food and transportation. Also, put aside some extra funds for unexpected costs that may come up during your trip to Chatham.
  3. Decide your trip length: Think about how much time you'd like to spend exploring Chatham. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a comfortable pace.
  4. Combine your accommodations and airfare: After you've settled on your travel dates and duration, lock in the right Chatham vacation package for you.

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