Chatham Vacations from ￥206,559
Book a Hotel + Flight or Car together to unlock savings
The Latest Chatham Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Red Lion Inn
￥268,329
per person
Dec 26 - Dec 30
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Albany (ALB)
8.8/10 Excellent! (1,014 reviews)
Would go there again but would request to be in the main Inn, they have properties all over the town center that are considered the Inn. That was disappointing.
A very unique property and super cute!
Reviewed on Oct 6, 2026
Find the Best Chatham Vacation Packages
Chatham Hotel Deals
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
￥12,718
￥15,942 total
Nov 1 - Nov 2
includes taxes & fees
8.8/10 Excellent! (2,735 reviews)
"It's like home away from home."
Reviewed on Oct 12, 2026
Country Inn & Suites by Radisson, Downtown Albany New York
300 Broadway Albany NY
Fully refundable
￥16,013
￥18,336 total
Nov 1 - Nov 2
includes taxes & fees
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
￥13,571
￥18,696 total
Nov 9 - Nov 10
includes taxes & fees
9/10 Wonderful! (1,200 reviews)
"Great place, peaceful, good management, comfortable, price is right. 👍"
Reviewed on Oct 12, 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
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.
Frequently asked questions
How much does a Chatham vacation package cost?
You'll find cheap prices from ￥206,559 on Expedia for your Chatham getaway. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation 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 vacation 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 vacation 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 vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking accommodations 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 vacation 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?
- Pick your dates: What you'd like to do in Chatham and your favorite season will help you decide when to get away.
- 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.
- 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.
- Combine your accommodations and airfare: After you've settled on your travel dates and duration, lock in the right Chatham vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.