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.
Saratoga Casino Hotel

Saratoga Casino Hotel

4 out of 5
Price was CA $996, price is now CA $838 per person
CA $838
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
9.4/10 Exceptional! (1,072 reviews)

South Shire

South Shire

4 out of 5
Price was CA $1,065, price is now CA $891 per person
CA $891
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
9/10 Wonderful! (137 reviews)

Hill Farm Inn

Hill Farm Inn

4 out of 5
Price was CA $1,266, price is now CA $1,124 per person
CA $1,124
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
9.6/10 Exceptional! (181 reviews)

Wilburton Inn

Wilburton Inn

3.5 out of 5
Price was CA $1,150, price is now CA $1,045 per person
CA $1,045
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
9/10 Wonderful! (136 reviews)
Beautiful serene large property with many interesting art sculptures throughout. Close to downtown Manchester but need car. Very memorable.

Reviewed on Oct 24, 2026

Ambler Hotel

Ambler Hotel

2 out of 5
Price was CA $995, price is now CA $911 per person
CA $911
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
8/10 Very good! (40 reviews)
Great Value. Everything was clean and up to date.

Reviewed on Nov 3, 2026

Ready to book your vacation to Chatham?

 

Choose your dates

Chatham Hotel Deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is CA $114 per night from Nov 10 to Nov 11
CA $114
CA $142 total
Nov 10 - Nov 11
includes taxes & fees
Vacation Village in the Berkshires
Country Inn & Suites by Radisson, Downtown Albany New York

Country Inn & Suites by Radisson, Downtown Albany New York

2.5 out of 5
300 Broadway Albany NY
Fully refundable
The price is CA $143 per night from Nov 22 to Nov 23
CA $143
CA $164 total
Nov 22 - Nov 23
includes taxes & fees
8.2/10 Very good! (1,248 reviews)
"Weird smell in the whole hotel. Not a great part of downtown Albany. I got there and there was no air conditioning unit in the room and was 77° in the room. They offered me a box fan and to open the window. I said I’m not staying here. They then offered to refund two of my three nights despite I ..."

Reviewed on Nov 9, 2026

Country Inn & Suites by Radisson, Downtown Albany New York
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is CA $108 per night from Dec 6 to Dec 7
CA $108
CA $153 total
Dec 6 - Dec 7
includes taxes & fees
Berkshire Mountain Lodge
See all 1,615 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.
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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.
See properties

Frequently asked questions

How much does a Chatham vacation package cost?
You can pick up a vacation package to this popular destination from CA $838 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?

  1. Pick your dates: What you plan to do in Chatham and your favourite season will help you decide when to get away.
  2. 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.
  3. 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.
  4. 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.