Chatham Holidays

Book a Hotel + Flight or Car together to unlock savings

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 3.843.598 ₫ per night from 21 Jul to 22 Jul
3.843.598 ₫
4.581.558 ₫ total
21 Jul - 22 Jul
includes taxes & fees
8.8/10 Excellent! (2,454 reviews)
"Exceptional price point in the Berkshies. Accomodations were spacious and clean. It met all our needs."

Reviewed on 17 Jul 2026

Vacation Village in the Berkshires
Country Inn & Suites by Radisson, Downtown Albany New York

Country Inn & Suites by Radisson, Downtown Albany New York

2.5 out of 5
300 Broadway Albany NY
Fully refundableReserve now, pay when you stay
The price is 2.830.119 ₫ per night from 16 Aug to 17 Aug
2.830.119 ₫
3.240.487 ₫ total
16 Aug - 17 Aug
includes taxes & fees
Country Inn & Suites by Radisson, Downtown Albany New York
Comfort Inn Glenmont - Albany South

Comfort Inn Glenmont - Albany South

2.5 out of 5
37 Route 9W Glenmont NY
The price is 2.488.086 ₫ per night from 26 Jul to 27 Jul
2.488.086 ₫
2.848.857 ₫ total
26 Jul - 27 Jul
includes taxes & fees
7.8/10 Good! (1,003 reviews)
"It was clean and comfortable. Nothing fancy, but it was a good stop as we were traveling through."

Reviewed on 16 Jul 2026

Comfort Inn Glenmont - Albany South
See all 1,625 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.

Stay near popular Chatham attractions

The Mac-Haydn Theatre

This intimate theater-in-the-round presents professional summer musicals with New York City talent. Every seat offers an immersive view of the dynamic performances, running from Memorial Day through Labour Day.
See properties

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.

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