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 AEDĀ 295 per night from Nov 15 to Nov 16
AEDĀ 295
AEDĀ 370 total
15 Nov - 16 Nov
includes taxes & fees
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 refundable
The price is AEDĀ 372 per night from Nov 22 to Nov 23
AEDĀ 372
AEDĀ 425 total
22 Nov - 23 Nov
includes taxes & fees
8.2/10 Very Good! (1,257 reviews)
"Thumbs up"

Reviewed on 11 November 2026

Country Inn & Suites by Radisson, Downtown Albany New York
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 AEDĀ 282 per night from Dec 6 to Dec 7
AEDĀ 282
AEDĀ 397 total
6 Dec - 7 Dec
includes taxes & fees
Berkshire Mountain Lodge
See all 1,605 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 Labor Day.
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Frequently asked questions

How much does a Chatham vacation package cost?
You can pick up a vacation package to this popular destination on Expedia. However, how much your vacation to Chatham costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Chatham?
To score cheap Chatham vacation packages, organize your trip outside of peak times like public holidays and major events. You'll generally find better availability and lower prices for flights and hotels.
How to find the best Chatham package deals?
Start your search for a Chatham package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Chatham package deal right away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Chatham adventure off to a flying start.
Is it cheaper to book a Chatham vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component individually. And you'll still get the flexibility to create a personalized Chatham vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Chatham?
If you're planning a spur-of-the-moment Chatham getaway, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can score sensational deals on your hotels and flights by booking well in advance.
How to plan a trip to Chatham?

  1. Pick your dates: What you plan to do in Chatham and your favorite season will help you decide when to get away.
  2. Set a budget: Consider costs like food, flights and transportation when working out how much to set aside for your trip to Chatham. Then, pick a property that matches your budget, whether that's a low-cost option or a high-end getaway.
  3. Decide how long to go for: Now that you know more about Chatham, you can figure out the ideal length of your vacation. Create a rough plan and give yourself enough time for all the things you want to do.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to find a Chatham vacation package that brings all your bookings together.