Chatham Vacations

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    Better together
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

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 ₩125,406 per night from Jul 5 to Jul 6
₩125,406
₩154,958 total
Jul 5 - Jul 6
includes taxes & fees
8.6/10 Excellent! (1,843 reviews)
"amazing for the price and overall SOOO clean"

Reviewed on Jun 28, 2025

Vacation Village in the Berkshires
Quality Inn
Quality Inn
2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is ₩160,260 per night from Jul 17 to Jul 18
₩160,260
₩179,010 total
Jul 17 - Jul 18
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"Great location, good price I wish the mattresses were firmer and an option for Netflix would be nice."

Reviewed on Jul 3, 2025

Quality Inn
Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham Lenox
2 out of 5
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is ₩134,285 per night from Jul 6 to Jul 7
₩134,285
₩149,992 total
Jul 6 - Jul 7
includes taxes & fees
7.4/10 Good! (746 reviews)
"I have stayed here on and off, and even during home renovations. It’s always clean and the staff are friendly, this is one of the best kept hotels in the area!"

Reviewed on Jun 26, 2025

Howard Johnson by Wyndham Lenox
See all 1,595 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.