Chatham Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to €185 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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
The price is €113 per night from 27 Aug to 28 Aug
€113
27 Aug - 28 Aug
includes taxes & fees
8.6/10 Excellent! (1,942 reviews)
"This Vacation Village is amazing, returning this week for a little time away. Stayed last week for work and came home and planned a 3 day trip based on the location."

Reviewed on 10 Aug 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
8.8/10 Excellent! (555 reviews)
"It was a great stay. The couches in the room were dirty and should be replaced."

Reviewed on 11 Aug 2025

Get rates
Berkshire Mountain Lodge
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is €68 per night from 27 Aug to 28 Aug
€68
27 Aug - 28 Aug
includes taxes & fees
5.2/10 (764 reviews)
"This family is professional and kind. I left a $100 tip because I watched attend to her guests and her two Autistic sons as well as her elderly parent. Amazing"

Reviewed on 2 Aug 2025

FairBridge Inn Express
See all 1,604 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.

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