Chesterfield Vacations from ￥421,916
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The Latest Chesterfield Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Wylie Inn and Conference Center at Endicott College
Price was ￥540,920, price is now ￥421,916 per person
￥421,916
per person
Jun 21 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.2/10 Wonderful! (1,185 reviews)
Conveniently located in Beverly
Reviewed on Apr 27, 2026
The Langham, Boston
Downtown Boston
Price was ￥901,040, price is now ￥628,909 per person
￥628,909
per person
Jun 21 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (1,007 reviews)
Service both at the hotel and restaurants was the one of the best experiences I’ve had
Reviewed on May 2, 2026
Eurostars The Boxer
West End
Price was ￥670,507, price is now ￥495,370 per person
￥495,370
per person
Jun 21 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8.8/10 Excellent! (1,451 reviews)
Staff very friendly. Night desk clerk, Mathew, was extremely helpful and engaging.
Wasn’t happy about being talked into a pre-usage amenity charge. Still not sure what it was supposed to be used for. This was a $69+ charger.
Also parking a block and half away was a $50 per day. Thought a bit high.
Reviewed on May 7, 2026
Revere Hotel Boston Common
Bay Village
Price was ￥695,280, price is now ￥524,217 per person
￥524,217
per person
Jun 21 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9/10 Wonderful! (1,990 reviews)
The pace was very nice easy to get wherever you wanted to go. The subway was a quick walk that could get you all over. All the staff was very friendly. The housekeeping done a great job daily
Reviewed on May 5, 2026
Hotel Commonwealth
Fenway–Kenmore
Price was ￥682,468, price is now ￥532,295 per person
￥532,295
per person
Jun 21 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.4/10 Exceptional! (2,056 reviews)
The staff always great. The location to Fenway and the subway was ideal. The view from our room could not have been better. Would definitely stay there again.
Reviewed on May 9, 2026
Find the Best Chesterfield Vacation Packages
Chesterfield Hotel Deals
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is ￥13,763 per night from May 24 to May 25
￥13,763
￥18,878 total
May 24 - May 25
includes taxes & fees
9/10 Wonderful! (925 reviews)
Room very spacious and clean. Full kitchen is a great bonus.
Reviewed on May 4, 2026
Hotel UMass
1 Campus Center Way Amherst MA
Fully refundableReserve now, pay when you stay
The price is ￥19,483 per night from May 25 to May 26
￥19,483
￥21,982 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
It was good! Great location!
Reviewed on May 5, 2026
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
The price is ￥27,407 per night from Jun 3 to Jun 4
￥27,407
￥32,067 total
Jun 3 - Jun 4
includes taxes & fees
9.2/10 Wonderful! (2,219 reviews)
The room was massive and roomy. The floor was shiny and clean. Everything was tidy. The bed and pillows were comfortable.
Reviewed on May 6, 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.
