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.
La Quinta Inn & Suites by Wyndham Latham Albany Airport

La Quinta Inn & Suites by Wyndham Latham Albany Airport

2.5 out of 5
per person
Jun. 6 - Jun. 10
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
7.4/10 Good! (1,000 reviews)
Convenient parking and exit at the back.

Reviewed on Apr. 28, 2025

Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
per person
Jun. 6 - Jun. 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.4/10 Exceptional! (397 reviews)
The view of Lake George from our balcony was spectacular! We also enjoyed the convenience of lakeside dining on premises at the Boathouse.

Reviewed on Apr. 27, 2025

Brookmere

Brookmere

2.5 out of 5
Save 100% on your flight
per person
Jun. 6 - Jun. 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9/10 Wonderful! (6 reviews)
Amazing for the price

Reviewed on Apr. 27, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
per person
Jun. 6 - Jun. 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
7.4/10 Good! (462 reviews)
We a been coming to the Equinox multiple times a year for over 20 years but had not been here in over a year because the last time I was there it was not a pleasant experience. I am happy to say things are back to being very enjoyable again and we will be back soon!

Reviewed on Apr. 25, 2025

Holiday Inn Express Suites Clifton Park by IHG

Holiday Inn Express Suites Clifton Park by IHG

2.5 out of 5
per person
Jun. 6 - Jun. 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9/10 Wonderful! (636 reviews)
Short stay, nothing went wrong, very clean property and very friendly & helpful staff.

Reviewed on Apr. 26, 2025

Ready to book your vacation to Chatham?

 

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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 CA $143 per night from Apr. 30 to May 1
CA $143
CA $159 total
includes taxes & fees
Apr 30 - May 1
9/10 Wonderful! (573 reviews)
Beautiful & Affordable!
"Excellent experience and gorgeous property! Will stay again next time we visit the Berkshires."

Reviewed on Apr. 27, 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 CA $141 per night from May 7 to May 8
CA $141
CA $161 total
includes taxes & fees
May 7 - May 8
7.8/10 Good! (968 reviews)
"Clean and close to Albany"

Reviewed on Apr. 19, 2025

Comfort Inn Glenmont - Albany South
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Black Swan Lee - Lenox, Ascend Hotel Collection
3 out of 5
435 Laurel St, Lee, MA
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Apr. 30 to May 1
CA $151
CA $169 total
includes taxes & fees
Apr 30 - May 1
9/10 Wonderful! (1,006 reviews)
"Friendly staff, great location for hiking and biking in the Berkshires."

Reviewed on Apr. 27, 2025

The Black Swan Lee - Lenox, Ascend Hotel Collection
See all 1,551 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Chatham vacation package cost?
You’ll find cheap prices from CA $883 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?

  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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.