Pittsfield Vacation Packages
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Your Pittsfield Vacation
When you book a Pittsfield vacation package, you can kick back and enjoy your escape to the fullest. Delve into the highlights of this exciting city knowing that all your travel arrangements have been looked after before you go. A trip to Pittsfield is a wonderful opportunity to sightsee. Be sure to stop by big-name attractions such as Bousquet Ski Area, Colonial Theater and Hancock Shaker Village. Expedia will help you escape the everyday. Tailor your vacation to Pittsfield to suit your style of travel, whatever that may look like.
Top Pittsfield Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires
Price was CA $900, price is now CA $819 per person
CA $819
per person
Oct 24 - Oct 26
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.6/10 Excellent! (1,986 reviews)
No food available at the hotel. The mini blinds were tangled in my room. Otherwise clean and fine but those two things annoyed me.
Reviewed on Sep. 7, 2025
The Cornell Inn, Lenox & The Berkshires
Price was CA $1,396, price is now CA $1,147 per person
CA $1,147
per person
Oct 24 - Oct 26
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9/10 Wonderful! (1,000 reviews)
Very nice place. Quiet. The breakfasts are included and are upscale with excellent staff service.
Unless you are young and don't care, make sure you get a ground floor room - the upstairs rooms require a walk up a large staircase, and are inconvenient.
Would definitely return.
Reviewed on Sep. 5, 2025
Club Wyndham Bentley Brook
Price was CA $1,024, price is now CA $910 per person
CA $910
per person
Oct 24 - Oct 26
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (536 reviews)
Loved all of the jacuzzis as well as the apartment condo style sleeping. So convenient for access to Jiminy Peak for summer fun and I'm sure it great for skiers.
Reviewed on Aug. 7, 2025
The Ponds at Foxhollow
Price was CA $1,045, price is now CA $937 per person
CA $937
per person
Oct 24 - Oct 26
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.6/10 Excellent! (127 reviews)
The property is beautiful and very walkable, and well-located with Tanglewood, The Mount, Shakespeare & Co and downtown Lenox extremely nearby. Onsite amenities such as clubhouse, tennis courts and pool are convenient and the individual units are nicely laid out.
The property is a bit older and could some updating/refreshing.
Reviewed on Sep. 3, 2025
Pittsfield Hotel Deals
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is CA $132 per night from Sep 8 to Sep 9
CA $132
CA $179 total
Sep 8 - Sep 9
includes taxes & fees
FairBridge Inn Express
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is CA $98 per night from Sep 8 to Sep 9
CA $98
CA $110 total
Sep 8 - Sep 9
includes taxes & fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
Fully refundable
The price is CA $151 per night from Sep 10 to Sep 11
CA $151
CA $168 total
Sep 10 - Sep 11
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.
Discover the most popular places to visit in Pittsfield
Hancock Shaker Village
You can browse the exhibits at Hancock Shaker Village, a museum with a storied past, during your trip to Pittsfield. Wander the lakeside in this quaint area.
Canoe Meadows Wildlife Sanctuary
You can take time to visit Canoe Meadows Wildlife Sanctuary during your travels to Pittsfield. Wander the lakeside in this family-friendly area.
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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.
