Chatham Vacations from ￥83,170

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The Latest Chatham Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
Jul 21 - Jul 24
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
9.6/10 Exceptional! (2,977 reviews)
Be mindful of what time you are checking in, it can get busy. Other than that it’s EXCELLENT!

Reviewed on Jun 19, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Jul 21 - Jul 24
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
9.8/10 Exceptional! (1,007 reviews)
Location for first time Boston visitors was really good as a lot area to explore by foot then you could Uber the rest. The staff and in-room dining was outstanding

Reviewed on Jun 16, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
Jul 21 - Jul 24
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
9.6/10 Exceptional! (1,000 reviews)
Had dinner at the restaurant unfortunately it was the greatest food. The salmon was grilled and was dry and over cooked. I also had fries that were over cooked. Not what I’d expect for a hotel and restaurant of this standard.

Reviewed on Jun 16, 2025

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Jul 21 - Jul 24
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
9.4/10 Exceptional! (347 reviews)
The staff were very helpful. The hotel is exceptionally clean and well appointed.

Reviewed on Jun 6, 2025

Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
Save 100% on your flight
per person
Jul 21 - Jul 24
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
8.6/10 Excellent! (1,588 reviews)
Beautiful view. Good location

Reviewed on Jun 16, 2025

Find the Best Chatham Vacation Packages

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 kilometers 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.

Chatham Hotel Deals

Chatham Bars Inn
Chatham Bars Inn
5 out of 5
297 Shore Rd, Chatham, MA
The price is ￥94,286 per night from Jul 9 to Jul 10
￥94,286
￥113,307 total
Jul 9 - Jul 10
includes taxes & fees
9/10 Wonderful! (766 reviews)
"The atmosphere and views are breathtaking. The staff was extremely cordial and doted over us while we celebrated our 50th anniversary."

Reviewed on Jun 12, 2025

Chatham Bars Inn
Chatham Wayside Inn
Chatham Wayside Inn
4 out of 5
512 Main St, Chatham, MA
9.2/10 Wonderful! (505 reviews)
"Staff was very nice and the location was in the middle of town. Perfect!"

Reviewed on Jun 16, 2025

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Chatham Wayside Inn
Greyfinch Chatham Inn
Greyfinch Chatham Inn
3 out of 5
946 Main Street (Rte 28), Chatham, MA
8.8/10 Excellent! (220 reviews)
Great place to stay close to it all.
"Great place. Convenient, friendly and accommodating. Freshly updated and looks great and comfortable. Only minor issue was AC question - Keep on Auto/Cool - otherwise won't work as hoped :)"

Reviewed on Jun 10, 2025

Get rates
Greyfinch Chatham Inn
See all 5,041 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?
Offering excellent value package deals from ￥83,170 on Expedia, you'll be pleasantly surprised at how much a vacation to Chatham costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chatham?
January, February and March are great times to search for cheap Chatham vacation packages. Choosing to travel in quieter periods means you'll typically find better prices on accommodations and flights.
How many days is enough for Chatham?
We'd recommend booking a Chatham vacation for a minimum of 3 days. This gives you time to tick off top attractions including Chatham Drama Guild and Monomoy National Wildlife Refuge, and also explore neighborhoods like South Chatham and South Harwich. You could even squeeze in one or two day trips beyond Chatham.
Is it worth booking a vacation package to Chatham?
Chatham has everything you need for a wonderful escape. Begin your Chatham vacation on a high note by checking out top attractions like Ridgevale Beach.
How to find the best Chatham package deals?
Start your search for a Chatham package deal by entering your destination and preferred trip dates under our "Packages" tab. Then add a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Chatham package deal straight away, just play around with your dates and search again. Remember 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 great savings when compared to booking flights and stays individually. Better still, you can tailor your Chatham trip to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Chatham?
If you're planning a spur-of-the-moment Chatham adventure, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can score incredible deals on your hotels and flights by booking well in advance.
How to plan a trip to Chatham?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Chatham.
  2. Work out your budget: Ensure you have enough money to cover everything from meals and transportation to activities and airfares. Your hotel will probably be the largest expense during your trip to Chatham.
  3. Determine how many days away: Start by compiling a list of the sights and activities you want to get to in Chatham. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a customized Chatham vacation package.

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