Chesterfield Vacations from ￥355,370
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The Latest Chesterfield Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel
North End
Save 100% on your flight
Price was ￥725,924, price is now ￥480,094 per person
￥480,094
per person
May 13 - May 17
just found
Roundtrip flight included
Osaka (KIX) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Everything was great, however the pool itself was not heated, it was cold and no one really stayed in it for that reason. Thankfully there was a hot tub.
Reviewed on Mar 23, 2026
Hotel AKA Boston Common
Downtown Boston
Save 100% on your flight
Price was ￥993,054, price is now ￥713,034 per person
￥713,034
per person
May 10 - May 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9/10 Wonderful! (1,522 reviews)
Great location for going to the theater. Friendly staff, easy parking and clean rooms. Would definitely stay here again.
Reviewed on Mar 23, 2026
The Lenox Hotel Boston
Back Bay
Price was ￥550,816, price is now ￥445,479 per person
￥445,479
per person
May 10 - May 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9.6/10 Exceptional! (1,431 reviews)
Lively lobby at night, multiple eat-drink options, classy decor, great location.
Reviewed on Mar 23, 2026
Find the Best Chesterfield Vacation Packages
Chesterfield Hotel Deals
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
The price is ￥17,294 per night from Mar 30 to Mar 31
￥17,294
￥20,090 total
Mar 30 - Mar 31
includes taxes & fees
9.4/10 Exceptional! (2,220 reviews)
The staff were very friendly, making the entire stay pleasant from check-in to check-out. The hotel was clean and well-maintained, and the surroundings were quiet, which made it easy to relax. The room was also quite spacious, providing plenty of comfort during the stay. It’s a great choice for anyone ...
Reviewed on Mar 23, 2026
Comfort Inn & Suites Hadley - Amherst
400 Russell St Hadley MA
Fully refundable
The price is ￥18,784 per night from Mar 30 to Mar 31
￥18,784
￥20,981 total
Mar 30 - Mar 31
includes taxes & fees
9.2/10 Wonderful! (1,006 reviews)
N/A
Reviewed on Mar 23, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is ￥14,411 per night from Mar 25 to Mar 26
￥14,411
￥19,634 total
Mar 25 - Mar 26
includes taxes & fees
9/10 Wonderful! (885 reviews)
very clean and friendly staff
Reviewed on Mar 24, 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.
