Chatham Vacation Packages

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Your Chatham Vacation

Spend less time travel planning and more time having thrilling adventures with a Chatham vacation package. The neighborhood of Harwich Center, which is great for golfing and festivals, makes a great base for your city escape. If your trip to Chatham includes some sightseeing, take in renowned attractions like Chatham Lighthouse Beach, Bank Street Beach and Chatham Lighthouse. Check out Expedia's extensive range of travel options and begin planning your ultimate vacation to Chatham now.

Top Chatham Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,008, price is now CA $536 per person
CA $536
per person
Nov 1 - Nov 3
found 10 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $3,757, price is now CA $2,202 per person
CA $2,202
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (147 reviews)
The Reffles Hotel is a fabulous place to stay. Hotel is amazing with a wonderful friendly staff.

Reviewed on Aug. 20, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $3,269, price is now CA $2,097 per person
CA $2,097
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
Loved everything about it. There wasn’t anything that felt uncomfortable and there was so much that was impressive.

Reviewed on Aug. 21, 2025

DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Allston
Price was CA $1,455, price is now CA $967 per person
CA $967
per person
Nov 2 - Nov 6
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (1,002 reviews)
Great Experience at a great location

Reviewed on Aug. 21, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was CA $2,825, price is now CA $1,908 per person
CA $1,908
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (441 reviews)
Beautiful building, friendly staff, great atmosphere

Reviewed on Aug. 16, 2025

Chatham Beach Vacation

There's nothing that can beat a Chatham vacation. Whether you're indulging in fancy cocktails at a local hot spot or flipping through a book by the shore, your trip to Chatham is the perfect time to live out your beachy dreams. Many travelers will tell you to stay near Ridgevale Beach, located just 3 kilometres from the town center. However, you'll also find a fantastic range of Chatham vacation packages close to Hardings Beach and Cockle Cove Beach, two other well-loved nearby options.

Ready to book your vacation to Chatham?

 

Choose your dates

Chatham Hotel Deals

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd, Chatham, MA
The price is CA $737 per night from Sep 22 to Sep 23
CA $737
CA $886 total
Sep 22 - Sep 23
includes taxes & fees
9.2/10 Wonderful! (782 reviews)
"5 star experience!!"

Reviewed on Aug. 4, 2025

Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St, Chatham, MA
The price is CA $373 per night from Sep 1 to Sep 2
CA $373
CA $483 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (538 reviews)
"Great hotel in perfect location. Easy parking and right in the Main Street. Lovely bar in hotel. Restaurant food good - service a little poor at restaurant. Breakfast choice not great….but overall a great stay and would recommend."

Reviewed on Aug. 17, 2025

Chatham Wayside Inn
Greyfinch Chatham Inn

Greyfinch Chatham Inn

3 out of 5
946 Main Street (Rte 28), Chatham, MA
The price is CA $311 per night from Sep 1 to Sep 2
CA $311
CA $403 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (234 reviews)
Greyfinch
"It was very nice. Property is clean, quiet, nice pool, close to main street, market, restaurants in walking distance. Rooms are very nice."

Reviewed on Jul. 25, 2025

Greyfinch Chatham Inn
See all 5,031 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

Discover the most popular places to visit in Chatham

Veterans Field

Catch an event at Veterans Field during your trip to Chatham. Wander the beautiful beaches and seaside in the area.

Veterans Field

Chatham Drama Guild

You can enjoy a show at Chatham Drama Guild during your trip to Chatham. Wander the area's beautiful beaches or simply enjoy one of its seafood restaurants.

Chatham Drama Guild

Monomoy Theatre

You can get tickets for a performance at Monomoy Theatre during your trip to Chatham. Wander the beautiful beaches and seaside in the area.

Monomoy Theatre

Frequently asked questions

How much does a Chatham vacation package cost?
You can grab a vacation package to this destination from CA $536 on Expedia. But how much your vacation to Chatham costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Chatham?
You're likely to find lower rates and greater availability in January, February and March. Explore our cheap Chatham vacation packages and you could land some great off-season discounts.
How many days is enough for Chatham?
We'd recommend booking a Chatham vacation for at least 3 days. This gives you time to check off key attractions including Bank Street Beach and Ridgevale Beach, as well as explore neighbourhoods like South Chatham and South Harwich. You could even make time for a day trip (or two) beyond Chatham.
Is it worth booking a vacation package to Chatham?
Chatham offers everything you need for a wonderful trip. Get your Chatham vacation off to a flying start by visiting top attractions like Ridgevale Beach.
How to find the best Chatham package deals?
Use Expedia's filters to find some tempting Chatham package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or look for Chatham package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Chatham vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and stays individually. Better still, you can personalize your Chatham trip to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Chatham?
Enjoy amazing discounts by reserving your flights in advance with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for a spur-of-the-moment Chatham trip.
How to plan a trip to Chatham?

  1. Choose your dates: The things you want to do in Chatham and your favourite season can help you decide when to go.
  2. Plan your budget wisely: On top of the price of your accommodations, you should consider other expenses too. These include flights, transportation and food. Also, put aside a little extra for unexpected costs that could crop up during your trip to Chatham.
  3. Set the duration of your trip: Start by compiling a list of the activities and attractions you want to experience in Chatham. Then, estimate how long you'll need at each, including any travel time.
  4. Combine your airfare and accommodations: Once you've nailed down your dates and duration, lock in the perfect 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.