Pittsfield Vacation Packages
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Top Pittsfield Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Raffles Boston
Back Bay
Price was CA $3,029, price is now CA $1,663 per person
CA $1,663
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
9.6/10 Exceptional! (154 reviews)
Staff went above and beyond everyday! The dining options and location were amazing.
Reviewed on Sep. 2, 2025
Boston Harbor Hotel
North End
Price was CA $2,163, price is now CA $1,411 per person
CA $1,411
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
Great harbor views! Room service was superb as well. Everyday we came back to an organized room and sometimes sweets, creams. The reception desk was also good in answering any questions. Excellent location. Would stay again.
Reviewed on Sep. 3, 2025
The Revolution Hotel
South End
Price was CA $1,510, price is now CA $1,001 per person
CA $1,001
per person
Oct 24 - Oct 28
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (2,140 reviews)
It was a great experience. A bit small for four people in one room. But we made due.
Reviewed on Sep. 2, 2025
The Langham, Boston
Downtown Boston
Price was CA $2,338, price is now CA $1,561 per person
CA $1,561
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,007 reviews)
First rate hotel. Definitely a Luxury hotel stay!
Reviewed on Sep. 1, 2025
Pittsfield Hotel Deals
Winnisquam Lake Inn
788 Laconia Rd, Tilton, NH
Fully refundableReserve now, pay when you stay
The price is CA $109 per night from Sep 4 to Sep 5
CA $109
CA $118 total
Sep 4 - Sep 5
includes taxes & fees
The Centennial
96 Pleasant St, Concord, NH
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from Sep 14 to Sep 15
CA $161
CA $197 total
Sep 14 - Sep 15
includes taxes & fees
Best Western Plus Landmark Inn
480 Main Street, Laconia, NH
Fully refundableReserve now, pay when you stay
The price is CA $157 per night from Sep 7 to Sep 8
CA $157
CA $170 total
Sep 7 - Sep 8
includes taxes & fees
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.