Chesterfield Vacations from ￥364,446
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The Latest Chesterfield Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Studio Allston Hotel
Brighton
Price was ￥444,936, price is now ￥364,446 per person
￥364,446
per person
Sep 11 - Sep 18
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8.6/10 Excellent! (1,274 reviews)
Nice place. Would definitely stay there again if in the area
Reviewed on Jun 22, 2026
Boston Harbor Hotel
North End
Price was ￥973,376, price is now ￥745,986 per person
￥745,986
per person
Sep 11 - Sep 18
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (1,009 reviews)
We were there for 5 days. It was impeccable. The location, service, ambiance everything was perfect! All small attentions that makes you feel comfortable. We took the water taxi from (and to) the airport directly to the hotel fastest way to get there. Easy to walk around and along the waterfront. Breakfast was excellent
Reviewed on Jun 15, 2026
The Charles Hotel
West Cambridge
Price was ￥554,170, price is now ￥438,606 per person
￥438,606
per person
Sep 11 - Sep 17
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.4/10 Exceptional! (1,001 reviews)
had a delicious muffin and coffee. Parking was safe and convenient.
Reviewed on Jun 22, 2026
The Newbury Boston
Back Bay
Price was ￥828,733, price is now ￥679,281 per person
￥679,281
per person
Sep 11 - Sep 18
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.4/10 Exceptional! (661 reviews)
Incredible staff. This is an amazing location and the breakfast is great
Reviewed on Jun 16, 2026
The Merchant
Downtown Salem
Price was ￥868,172, price is now ￥714,984 per person
￥714,984
per person
Sep 11 - Sep 18
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (424 reviews)
Perfect property and GREAT location. Walking distance to dining and Salem sites.
Reviewed on Jun 10, 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 ￥16,906 per night from Jul 15 to Jul 16
￥16,906
￥19,780 total
Jul 15 - Jul 16
includes taxes & fees
9.2/10 Wonderful! (2,155 reviews)
"Very nice place to stay. Nice pool and hot tub"
Reviewed on Jun 24, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is ￥22,703 per night from Jul 26 to Jul 27
￥22,703
￥28,973 total
Jul 26 - Jul 27
includes taxes & fees
9/10 Wonderful! (999 reviews)
"We thoroughly enjoyed our stay. The rooms are spacious and beautifully furnished, and having a stove and refrigerator along with a separate living/dining room was a definite plus. The 24/7 coffee and hot chocolate machine in the lobby was another perk, as were the hot tub and large (albeit shallow) ..."
Reviewed on Jun 24, 2026
Hotel UMass
1 Campus Center Way Amherst MA
Fully refundableReserve now, pay when you stay
The price is ￥21,598 per night from Jul 1 to Jul 2
￥21,598
￥24,350 total
Jul 1 - Jul 2
includes taxes & fees
8.8/10 Excellent! (1,014 reviews)
"Really convenient"
Reviewed on Jun 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.
