
Chatham Vacations from ¥375,908
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The Latest Chatham Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Arcadian Hotel
Coolidge Corner
Price was ¥408,302, price is now ¥375,908 per person
¥375,908
per person
Aug 16 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Boston (BOS)
8/10 Very Good! (4,123 reviews)
Very nice room wasn’t quite like the pictures but still nice had a a bit of a hot water issue in the morning and a wet stain in the carpet but staff was nice
Reviewed on Jun 9, 2026


Eurostars The Boxer
West End
Price was ¥472,915, price is now ¥415,409 per person
¥415,409
per person
Aug 16 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Boston (BOS)
8.8/10 Excellent! (1,507 reviews)
It’s a great location and really good rooms. I liked the breakfast. One of the horrible things that happened was a guest created a very loud situation for an extended period of time. The hotel sided with the guest creating the situation. So if you need help or a problem resolved. The hotel point blank said they are not going to do anything about it and you are on your own. Very bizarre behavior by a hotel. Never really saw this before.
Everything else was great. Clean rooms and everything was modern and nice.
Reviewed on Jun 8, 2026

Mandarin Oriental, Boston
Back Bay
Price was ¥695,317, price is now ¥628,971 per person
¥628,971
per person
Aug 16 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Boston (BOS)
9.4/10 Exceptional! (425 reviews)
The valet was fast and professional, the room was clean, the staff are very helpful. I would definitely stay again!
Reviewed on May 25, 2026

The Liberty, a Marriott Luxury Collection Hotel, Boston
West End
Price was ¥511,926, price is now ¥469,332 per person
¥469,332
per person
Aug 16 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Boston (BOS)
8.8/10 Excellent! (1,005 reviews)
Unique hotel. Great vibe.
Reviewed on Jun 5, 2026
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
297 Shore Rd Chatham MA
The price is ¥155,956 per night from Jun 23 to Jun 24
¥155,956
¥178,492 total
Jun 23 - Jun 24
includes taxes & fees
9.2/10 Wonderful! (835 reviews)
"Lovely hotel. We had a cottage which had lovely views out across the sandbars. Only downside was the weather but that wasn’t an issue in such lovely surroundings."
Reviewed on Jun 5, 2026

Chatham Wayside Inn
512 Main St Chatham MA
The price is ¥71,526 per night from Jun 14 to Jun 15
¥71,526
¥88,828 total
Jun 14 - Jun 15
includes taxes & fees
9.2/10 Wonderful! (688 reviews)
"room was clean, friendly staff. for a room of 4 there were only 2 accessible outlets, however one was not properly working. we had a long charging cable that we connected to the outlet in the bathroom which was not ideal but was able to make it work. very central hotel with close proximity to restaurants ..."
Reviewed on Jun 8, 2026

Queen Anne Inn
70 Queen Anne Rd Chatham MA
The price is ¥46,703 per night from Jun 10 to Jun 11
¥46,703
¥53,451 total
Jun 10 - Jun 11
includes taxes & fees
8.8/10 Excellent! (239 reviews)
"It is an old property and very tired. Not very clean."
Reviewed on Jun 9, 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
