Chatham Vacations

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Find the Best Chatham Vacation Packages

Chatham Hotel Deals

Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AED 355 per night from Apr 17 to Apr 18
AED 355
AED 397 total
includes taxes & fees
17 Apr - 18 Apr
9/10 Wonderful! (539 reviews)
"Enjoyed having an excellent meal and bar was very convenient."

Reviewed on 30 March 2025

Life House Berkshires
Comfort Inn Glenmont - Albany South
Comfort Inn Glenmont - Albany South
2.5 out of 5
37 Route 9W, Glenmont, NY
Fully refundable
The price is AED 353 per night from May 4 to May 5
AED 353
AED 404 total
includes taxes & fees
4 May - 5 May
7.8/10 Good! (953 reviews)
"It was fine!"

Reviewed on 23 March 2025

Comfort Inn Glenmont - Albany South
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AED 325 per night from Apr 15 to Apr 16
AED 325
AED 363 total
includes taxes & fees
15 Apr - 16 Apr
9/10 Wonderful! (1,003 reviews)
Great but firm mattress
"Great location and the room was very nice. The only issue I had was the bed was very firm."

Reviewed on 2 April 2025

The Yankee, Trademark Collection by Wyndham
See all 1,544 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 vacation 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 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 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?

  1. Pick your dates: What you’d like to do in Chatham and your favorite 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 accommodations and airfare: After you’ve settled on your travel dates and duration, lock in the right Chatham vacation package for you.

Discover the most popular places to visit in Chatham

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.

The Mac-Haydn Theatre