Chatham Packages (Flight + Hotel)

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Top hotels in Chatham

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
8.6/10 Excellent! (1,882 reviews)
"This is a great get away! Beautiful atmosphere and lots of variety of activities"

Reviewed on 17 Jul 2025

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Vacation Village in the Berkshires
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is ฿14,045 per night from 25 Jul to 26 Jul
฿14,045
฿15,688 total
25 Jul - 26 Jul
includes taxes & fees
9/10 Wonderful! (635 reviews)
"this property is amazing, the only thing is it's right next to a highway, so the noise is not so cool, but from the inside you can't hear any traffic noise."

Reviewed on 15 Jul 2025

Berkshires Untold
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is ฿4,112 per night from 27 Jul to 28 Jul
฿4,112
฿4,593 total
27 Jul - 28 Jul
includes taxes & fees
8.4/10 Very Good! (1,013 reviews)
"Friendliness and cleanliness"

Reviewed on 15 Jul 2025

Best Western Plus Berkshire Hills Inn & Suites
See all 1,603 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 holiday 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 holiday 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 holiday 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 holiday 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 holiday as a package?
An Expedia holiday package could land you considerable savings when compared to booking accommodation 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 holiday 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 favourite 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 accommodation and airfare: After you've settled on your travel dates and duration, lock in the right Chatham holiday package for you.