Chatham Vacations from ￥331,178

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The Latest Chatham Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Cambridge Common House

Cambridge Common House

4 out of 5
West Cambridge
Price was ￥372,310, price is now ￥331,178 per person
￥331,178
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
10/10 Exceptional! (17 reviews)
What an absolutely beautiful hotel, filled with lovely, tasteful touches, and an incredibly kind and attentive staff. I can’t wait to go back and stay again!

Reviewed on Jul 17, 2026

The Charles Hotel

The Charles Hotel

5 out of 5
West Cambridge
Price was ￥446,632, price is now ￥368,162 per person
￥368,162
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.4/10 Exceptional! (1,011 reviews)

The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Allston
Price was ￥408,047, price is now ￥343,224 per person
￥343,224
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.4/10 Exceptional! (198 reviews)

Iris Hotel Boston

Iris Hotel Boston

4 out of 5
Coolidge Corner
Price was ￥401,591, price is now ￥350,022 per person
￥350,022
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.4/10 Exceptional! (603 reviews)
Er love it, we have stayed there a few times, great location

Reviewed on Jul 19, 2026

Hotel Commonwealth

Hotel Commonwealth

4.5 out of 5
Fenway–Kenmore
Price was ￥439,271, price is now ￥392,348 per person
￥392,348
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.4/10 Exceptional! (2,195 reviews)

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 ￥253,792 per night from Jul 26 to Jul 27
￥253,792
￥290,465 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (846 reviews)
"Amazing hospitality, food and location!"

Reviewed on Jul 21, 2026

Chatham Bars Inn
Queen Anne Inn

Queen Anne Inn

4 out of 5
70 Queen Anne Rd Chatham MA
The price is ￥46,072 per night from Aug 5 to Aug 6
￥46,072
￥52,730 total
Aug 5 - Aug 6
includes taxes & fees
Queen Anne Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St Chatham MA
The price is ￥83,888 per night from Aug 3 to Aug 4
￥83,888
￥103,078 total
Aug 3 - Aug 4
includes taxes & fees
Chatham Wayside Inn
See all 5,063 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.

Stay near popular Chatham attractions

A calm sea with several boats anchored near the shore.

Chatham Fish Pier

9.4/10 (107 reviews)
Watch local fishermen unload their daily catch while seals swim nearby at this authentic working waterfront. Savor fresh seafood from the on-site market while enjoying panoramic harbor views from the observation deck.
See properties

What to do in Chatham

Cape Cod Helicopter Day Excursion

Cape Cod Helicopter Day Excursion

￥188,123
per adult
Cape Cod Helicopter Day Excursion
See all activities in Chatham

Frequently asked questions

How much does a Chatham vacation package cost?
Offering excellent value package deals from ￥331,178 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.