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 Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
per person
Jun. 6 - Jun. 10
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
7.4/10 Good! (462 reviews)
Outdated room (old, scuffed furniture and carpet) in need of a facelift.

Reviewed on Mar. 16, 2025

Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
per person
Jun. 6 - Jun. 10
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.4/10 Exceptional! (397 reviews)
Did not understand that I would not be on water or beach. No staff upon arrival at 6pm which was scary and very disappointing. Overall not happy with stay. Feel i should receive a discounted refund

Reviewed on Apr. 5, 2025

Brookmere

Brookmere

2.5 out of 5
per person
Jun. 6 - Jun. 10
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9/10 Wonderful! (6 reviews)
The property is nice and the restaurant was wonderful but the “spa” is minimal and other than that there is nothing to do. No hot tub, no sauna, no games, not even a deck of cards, nothing. I had much higher expectations.

Reviewed on Mar. 7, 2025

The Hotel Saratoga, Ascend Hotel Collection

The Hotel Saratoga, Ascend Hotel Collection

3 out of 5
per person
Jun. 6 - Jun. 10
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.6/10 Excellent! (1,006 reviews)
Everything was perfect!

Reviewed on Mar. 30, 2025

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
per person
Jun. 6 - Jun. 10
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.4/10 Exceptional! (753 reviews)
I had another lovely stay at the Kimpton Taconic Hotel in Manchester, VT. This was my second time staying with my family of four, plus a group of friends. The beds are extremely comfortable, and the pillows are soft — just the way I like them. The hotel’s location is excellent, with a short drive to both Stratton Mountain Resort and Bromley Mountain Ski Resort. The on-site restaurant, The Copper Grouse, is a solid option for food, and the town of Manchester is so quaint, with charming shops, a supermarket, and plenty of great restaurants — all within walking distance from the hotel. We’ll definitely be back for our next skiing trip!

Reviewed on Apr. 1, 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 $154 per night from Apr. 7 to Apr. 8
CA $154
CA $172 total
includes taxes & fees
Apr 7 - Apr 8
9/10 Wonderful! (540 reviews)
"A motel style well thought out hotel, tastefully designed,very comfortable room with fabulous beds. Have no hesitation in recommending it."

Reviewed on Apr. 2, 2025

Life House Berkshires
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 CA $126 per night from Apr. 14 to Apr. 15
CA $126
CA $140 total
includes taxes & fees
Apr 14 - Apr 15
9/10 Wonderful! (1,004 reviews)
"Comfortable beds"

Reviewed on Apr. 3, 2025

The Yankee, Trademark Collection by Wyndham
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 out of 5
190 Meadow Street, South Lee, MA
Fully refundable
The price is CA $169 per night from Apr. 7 to Apr. 8
CA $169
CA $209 total
includes taxes & fees
Apr 7 - Apr 8
8.8/10 Excellent! (615 reviews)
"Clean and great location"

Reviewed on Mar. 28, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
See all 1,547 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 $914 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.