Chesterfield Vacations from ￥66,134
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The Latest Chesterfield Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Raffles Boston
Back Bay
Save 100% on your flight
Price was ￥243,122, price is now ￥158,602 per person
￥158,602
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (181 reviews)
It was ok noting like the one overseas.
Reviewed on Dec 7, 2025
Cambria Hotel Boston Somerville
Spring Hill
Price was ￥104,832, price is now ￥79,231 per person
￥79,231
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,003 reviews)
We did not have time to try the breakfast but the hotel was beautiful, the lobby was so inviting and the staff was friendly. The rooms were nice,well equipped and very quiet despite the city location. Highly recommend.
Reviewed on Dec 22, 2025
Embassy Suites Boston Logan Airport
East Boston
Price was ￥108,656, price is now ￥82,874 per person
￥82,874
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (2,118 reviews)
Room was very nice with plenty of space and light. The Hotel is a 5 minute walk to Santarpios, the best pizza and spicy sausage in Boston.
Reviewed on Dec 22, 2025
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 ￥17,233 per night from Jan 1 to Jan 2
￥17,233
￥20,019 total
Jan 1 - Jan 2, 2026
includes taxes & fees
9.2/10 Wonderful! (2,245 reviews)
Breakfast was very nice. The beds were super comfy. We lived the hot tub.
Reviewed on Dec 21, 2025
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Fully refundable
The price is ￥14,623 per night from Dec 25 to Dec 26
￥14,623
￥16,333 total
Dec 25 - Dec 26
includes taxes & fees
8/10 Very Good! (995 reviews)
While waiting for our vallet car due to construction. The hotel staff were engaging and had personal conversations with us. Rooms were good and all staff treated us exceptional. Give them an atta boy on proformance
Reviewed on Dec 22, 2025
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
The price is ￥15,567 per night from Jan 11 to Jan 12
￥15,567
￥20,913 total
Jan 11 - Jan 12, 2026
includes taxes & fees
9/10 Wonderful! (792 reviews)
Spacious room and loved pool and hot tub!
Reviewed on Dec 19, 2025
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.
