
Chester Vacations from ¥272,380
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ¥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Chester Vacation Packages
Price found within the past 48 hours. Click for updated prices.

The Colonnade Hotel Back Bay
Back Bay
Price was ¥339,834, price is now ¥272,380 per person
¥272,380
per person
Mar 26 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9.2/10 Wonderful! (2,268 reviews)
Easy check in, courteous staff, clean rm and great view. Prudential mall across Huntington Ave..
Reviewed on Feb 2, 2026


The Whitney Hotel
Beacon Hill
Price was ¥382,569, price is now ¥310,410 per person
¥310,410
per person
Mar 26 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9.6/10 Exceptional! (482 reviews)
Excellent property conveniently located in Beacon Hill. Rooms are a tad on the small side but well appointed and clean.
Reviewed on Feb 7, 2026

The Langham, Boston
Downtown Boston
Price was ¥398,388, price is now ¥329,831 per person
¥329,831
per person
Mar 26 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Perfect service, quite classic luxury hotel. We had a perfect stay and look forward to our next stay. Thank you
Reviewed on Feb 3, 2026

Global Luxury Suites Downtown Boston
Chinatown
Price was ¥476,006, price is now ¥411,535 per person
¥411,535
per person
Apr 23 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Nagoya (NGO) to Boston (BOS)
8/10 Very Good! (621 reviews)
The location where the hotel is. The 2/2 room has plenty of space. First time in Boston amazing hotel!!
Reviewed on Feb 8, 2026
Find the Best Chester Vacation Packages
Chester Hotel Deals

DoubleTree by Hilton Manchester Downtown
700 Elm St. Manchester NH
Fully refundableReserve now, pay when you stay
The price is ¥18,723 per night from Feb 16 to Feb 17
¥18,723
¥20,314 total
Feb 16 - Feb 17
includes taxes & fees
9/10 Wonderful! (1,134 reviews)
Room was great
Reviewed on Feb 6, 2026

La Quinta Inn & Suites by Wyndham Salem NH
8 Keewaydin Dr Salem NH
Fully refundableReserve now, pay when you stay
The price is ¥11,278 per night from Feb 15 to Feb 16
¥11,278
¥12,236 total
Feb 15 - Feb 16
includes taxes & fees
8.2/10 Very Good! (1,094 reviews)
Great spot
Reviewed on Feb 7, 2026

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
76 Mountain Rd Epsom NH
The price is ¥15,501 per night from Feb 23 to Feb 24
¥15,501
¥23,469 total
Feb 23 - Feb 24
includes taxes & fees
9.6/10 Exceptional! (116 reviews)
Good
Reviewed on Feb 7, 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
