Pittsfield Vacation Packages
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Top Pittsfield Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Colonnade Hotel Back Bay
Back Bay
Price was CA $1,885, price is now CA $1,400 per person
CA $1,400
per person
May 6 - May 9
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.2/10 Wonderful! (2,268 reviews)
Easy check in, courteous staff, clean rm and great view. Prudential mall across Huntington Ave..
Reviewed on Feb 2, 2026
Boston Harbor Hotel
North End
Price was CA $2,297, price is now CA $1,591 per person
CA $1,591
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.
Reviewed on Jan 25, 2026
The Langham, Boston
Downtown Boston
Price was CA $2,384, price is now CA $1,736 per person
CA $1,736
per person
May 6 - May 9
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Perfect service, quite classic luxury hotel. We had a perfect stay and look forward to our next stay. Thank you
Reviewed on Feb 3, 2026
Maverick Suites at 402 Columbus Ave
South End
Price was CA $1,825, price is now CA $1,413 per person
CA $1,413
per person
May 7 - May 12
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
7.8/10 Good! (66 reviews)
Biggest problem was that I never got the email with the access codes after checking in online. The place has no personnel on site, so I couldn't get in when it was really cold outside. Had to call customer service, where it was resolved. Within a few minutes.
I could hear pretty much everything that went on in the room next door, and even when people just went up and down the stairs in front of my room, I could hear everything.
The view out of the window is pretty terrible. It's basically just looking into other peoples' pretty wild back yards. Perhaps in the summer it looks a bit nicer.
Reviewed on Dec 6, 2025
Pittsfield Hotel Deals
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
76 Mountain Rd Epsom NH
The price is CA $137 per night from Feb 19 to Feb 20
CA $137
CA $208 total
Feb 19 - Feb 20
includes taxes & fees
9.6/10 Exceptional! (116 reviews)
Good
Reviewed on Feb 7, 2026
The Centennial
96 Pleasant St Concord NH
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,000 reviews)
We loved the atmosphere. You could tell it is an old building and it looks beautiful from the outside. The room was surprisingly spacious. The only downside is the elevator wasn't working, but we were only on the second floor so it wasn't a problem for us.
Reviewed on Feb 1, 2026
Hampton Inn by Hilton Concord/Bow
515 South St Bow NH
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from Feb 25 to Feb 26
CA $144
CA $156 total
Feb 25 - Feb 26
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
The room was ver y nice, clean and comfortable. Check in staff were friendly and helpful.
Reviewed on Feb 5, 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.
