Pittsfield Vacation Packages
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Top Pittsfield Vacation Deals
Price found within the past 48 hours. Click for updated prices.
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 11 hours 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
The Inn at Hastings Park, Relais & Chateaux - Boston
Price was CA $3,227, price is now CA $2,056 per person
CA $2,056
per person
Jul 11 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.6/10 Exceptional! (255 reviews)
Splendid bed and breakfast
Reviewed on Apr 29, 2026
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat
Price was CA $6,417, price is now CA $4,239 per person
CA $4,239
per person
Jul 20 - Jul 25
found 10 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Boston (BOS)
10/10 Exceptional! (9 reviews)
thanks u for very nice place and clean i really loved i will cominng back soon
Reviewed on May 8, 2025
Pittsfield Hotel Deals
Bower Cabin- Cabin in woods on a remote pond, Romantic getaway, Green living!
Pittsfield NH
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! (1,001 reviews)
"Clean friendly, great location"
Reviewed on May 13, 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.
