Pittsfield Vacations from ₩1,034,952
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The Latest Pittsfield Vacation Packages
Price found within the past 48 hours. Click for updated prices.
enVision Hotel Boston Everett
Price was ₩1,366,132, price is now ₩1,034,952 per person
₩1,034,952
per person
May 22 - May 25
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
8.6/10 Excellent! (1,009 reviews)
Staff was super friendly and courteous, place was spotless and a very fair price
Reviewed on Apr 9, 2026
Boston Harbor Hotel
North End
Save 100% on your flight
Price was ₩3,232,290, price is now ₩2,035,778 per person
₩2,035,778
per person
May 22 - May 25
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)
Fantastic hotel with beautiful waterfront rooms. Attention to details in the room were excellent. This is a true 5 star hotel.
Reviewed on Apr 10, 2026
Eurostars The Boxer
West End
Save 100% on your flight
Price was ₩1,822,811, price is now ₩1,256,010 per person
₩1,256,010
per person
May 22 - May 25
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
8.8/10 Excellent! (1,426 reviews)
Staff was great room was cute!
Reviewed on Apr 10, 2026
Club Quarters Hotel Faneuil Hall, Boston
Downtown Boston
Price was ₩1,554,038, price is now ₩1,188,262 per person
₩1,188,262
per person
May 22 - May 25
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9/10 Wonderful! (3,000 reviews)
Great location and clean!
Reviewed on Apr 11, 2026
Find the Best Pittsfield Vacation Packages
Pittsfield Hotel Deals
Steele Hill Resorts
516 Steele Hill Road Sanbornton NH
The price is ₩280,323 per night from May 11 to May 12
₩280,323
₩304,158 total
May 11 - May 12
includes taxes & fees
8.4/10 Very Good! (802 reviews)
The easter buffet was over priced, my daughter just turned 12 and was charged as an adult..we literally had a couple pieces of bacon/sausage and a waffle…my son had a couple pieces of bacon and some fruit and it cost us $111, it was disappointing but the rest of the stay was amazing!
Reviewed on Apr 7, 2026
Winnisquam Lake Inn
788 Laconia Rd Tilton NH
Fully refundableReserve now, pay when you stay
The price is ₩117,172 per night from May 7 to May 8
₩117,172
₩127,139 total
May 7 - May 8
includes taxes & fees
6.8/10 (836 reviews)
While the staff were nice, the room has mold on the curtains but they claimed it was from water from the AC. There were no night stands to put belongings and the hot water did not work in the shower.
Reviewed on Mar 29, 2026
Best Western Plus Landmark Inn
480 Main Street Laconia NH
Fully refundableReserve now, pay when you stay
The price is ₩167,993 per night from May 7 to May 8
₩167,993
₩182,272 total
May 7 - May 8
includes taxes & fees
7.8/10 Good! (1,001 reviews)
Yesss
Reviewed on Apr 2, 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.
