Pittsfield Vacation Packages
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Top Pittsfield Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Meco Hotel - Hostel
West End
Price was CA $1,963, price is now CA $1,146 per person
CA $1,146
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.6/10 Excellent! (414 reviews)
Great access very cheep.
Was not expecting that much for a reasonable price, but was surprised when they had a 24h autolock, well furnished and clean bunkers, and most importantly, well mannerred room mates. Also had a small snack stand, free coffee in the morning which made me very happy.
would love to stay here again!
Reviewed on May 18, 2026
By the Sea Guests Bed & Breakfast & Suites
Price was CA $2,487, price is now CA $1,561 per person
CA $1,561
per person
Jun 24 - Jun 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (185 reviews)
Our room had an wonderful Ocean View. The room was excellent and meals were awesome. Staff were very helpful. We will be going back next year!
Reviewed on Sep 20, 2025
Mandarin Oriental, Boston
Back Bay
Price was CA $2,517, price is now CA $1,729 per person
CA $1,729
per person
Jul 31 - Aug 3
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (421 reviews)
This is not a blow, your socks off property by any means! Dated and just ok. You’ll get the same thing for far less expense at a Sheraton, Hilton or Hyatt. Staff waa nice. There was nothing bad but certainly nothing spectacular or memorable to rave about.
Reviewed on Apr 29, 2026
Pittsfield Hotel Deals
Bower Cabin- Cabin in woods on a remote pond, Romantic getaway, Green living!
Pittsfield NH
10/10 Exceptional! (38 reviews)
"The cabin had everything we needed for a perfect peaceful getaway"
Reviewed on May 3, 2026
Steele Hill Resorts
516 Steele Hill Road Sanbornton NH
8.4/10 Very Good! (817 reviews)
"This hotel was excellent—spotless rooms, friendly staff, and a perfect location. I would definitely stay here again"
Reviewed on May 18, 2026
Hampton Inn by Hilton Concord/Bow
515 South St Bow NH
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from May 31 to Jun 1
CA $150
CA $163 total
May 31 - Jun 1
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"Room is clean"
Reviewed on May 19, 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.
