Chatham Vacation Packages
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Your Chatham Vacation
The adventure-packed city of Chatham is calling. Delve into everything from its highlights to its hidden gems with a Chatham vacation package that's customized to you. Any trip to Chatham needs a well-planned itinerary. Fill yours with attractions like Martin Van Buren National Historic Site, Art Omi International Arts Center - Fields Sculpture Park and The Mac-Haydn Theatre. Browse Expedia's wide range of travel options and start organizing your ideal vacation to Chatham today.
Top Chatham Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Whitlock
CA $811
per person
Nov 30 - Dec 4
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Albany (ALB)
8.4/10 Very good! (385 reviews)
The hotel staff were very friendly and helpful. There is ample parking and the location in town is great for walking to shops and restaurants. This is a very nice property.
Reviewed on Sep 25, 2026
Hideaway Inn Lenox
CA $866
per person
Nov 30 - Dec 4
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Albany (ALB)
7.8/10 Good! (60 reviews)
Easy check in, but a bit different since there is no staff to help check in. Had to find things on your own, but that was not difficult. Outside furniture could use and upgrade as our friends almost fell through the chair. But is was wonderful being able to sit outside, have appetizers, and play a game or just relax. All other guests we ran into were nice. I would return.
Reviewed on Sep 18, 2026
Holiday Inn Club Vacations Oak 'n Spruce Resort
CA $703
per person
Nov 30 - Dec 4
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Albany (ALB)
9.2/10 Wonderful! (989 reviews)
The room was very nice. Updated and clean Miniature golf fun . A lot of things to do. The staff pleasant and helpful. Would stay again
Reviewed on Sep 28, 2026
Ready to book your vacation to Chatham?
Chatham Hotel Deals
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
CA $135
CA $166 total
Sep 30 - Oct 1
includes taxes & fees
8.8/10 Excellent! (2,683 reviews)
"The temperature in the bedroom was very cold"
Reviewed on Sep 28, 2026
Country Inn & Suites by Radisson, Downtown Albany New York
300 Broadway Albany NY
Fully refundable
CA $155
CA $178 total
Oct 4 - Oct 5
includes taxes & fees
8.2/10 Very good! (1,103 reviews)
"Todo bien excelente muy bueno"
Reviewed on Sep 28, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
CA $111
CA $156 total
Oct 1 - Oct 2
includes taxes & fees
9/10 Wonderful! (1,159 reviews)
"The problem with the suites is that the cooking smell of the adjoining kitchen can really permeate throughout the entire space. So whoever cooked like a tomato sauce or something before I was there, I could really smell it in the bedroom. The bed was very comfortable though. The room was clean. The ..."
Reviewed on Sep 28, 2026
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
You can enjoy a show at The Mac-Haydn Theatre on your trip to Chatham. Stroll along this trendy area's riverfront, or simply enjoy its coffeehouses.
Frequently asked questions
How much does a Chatham vacation package cost?
You can pick up a vacation package to this popular destination from CA $675 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 many days is enough for Chatham?
Usually, a handful of days is enough to visit the top attractions during your Chatham vacation. However, if you want to have some time to rest or go on day tours, think about extending your itinerary.
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?
- Pick your dates: What you plan to do in Chatham and your favourite season will help you decide when to get away.
- 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.
- 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.
- 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
