Title: Pittsfield Vacation Packages 2026 | Expedia.com [Pittsfield Travel Guide](https://expedia.com/Pittsfield.dx9478)[Hotels in Pittsfield](https://expedia.com/Pittsfield-Hotels.d9478.Travel-Guide-Hotels)[Vacation Rentals in Pittsfield](https://expedia.com/Pittsfield-Vacation-Rentals.d9478.Travel-Guide-VacationRentals)[Flights to Pittsfield](https://expedia.com/Cheap-Flights-To-Pittsfield.d9478.Travel-Guide-Flights)[Car Rentals in Pittsfield](https://expedia.com/Car-Rentals-In-Pittsfield.d9478.Car-Rental-Guide) ![](https://images.trvl-media.com/place/9478/5d9f4527-2b11-4f19-a1cd-36a7128d1304.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Pittsfield Vacations ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## 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](https://www.expedia.com/Bousquet-Ski-Area-Pittsfield.d553248621532665283.Vacation-Attraction), [Colonial Theater](https://www.expedia.com/Colonial-Theater-Pittsfield.d553248621532665289.Vacation-Attraction) and [Hancock Shaker Village](https://www.expedia.com/Hancock-Shaker-Village-Pittsfield.d6091849.Vacation-Attraction). Expedia will help you escape the everyday. Tailor your vacation to Pittsfield to suit your style of travel, whatever that may look like. ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_9478) ### Discover the most popular places to visit in Pittsfield ![Hardly anyone here! Great way to spend a week day, skiing and tubing!](https://images.trvl-media.com/place/9478/3e445f06-d8fa-4c0f-888a-235912f60bb4.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Bousquet Ski Area Hit the slopes at Bousquet Ski Area during your trip to Pittsfield. Wander the lakeside in this family-friendly area. [](https://expedia.com/Bousquet-Ski-Area-Pittsfield.d553248621532665283.Vacation-Attraction) ![Hancock Shaker Village, Hancock Massachusetts beautiful place; description Shakers, all supported themselves by the proceeds of their farmland. The Hancock Shakers were primarily dairy farmers. The raising and sale of garden seeds was perhaps the most lucrative of their early businesses.Land acquisition and conversion continued for decades, with the area peaking at 3,000 acres](https://images.trvl-media.com/place/112303/51d1465f-7568-4ca1-ab97-760ab0d2a7f2.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.com/Hancock-Shaker-Village-Pittsfield.d6091849.Vacation-Attraction) ![View of peak foliage in the Berkshires. ](https://images.trvl-media.com/place/9478/0f986732-b8a4-46bb-a277-3b8822746673.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Berkshire Museum You can spend an afternoon exploring the galleries in Berkshire Museum during your trip to Pittsfield. Wander the lakeside in this family-friendly area. [](https://expedia.com/Berkshire-Museum-Pittsfield.d553248621532665288.Vacation-Attraction) ## Pittsfield Hotel Deals ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Berkshire Mountain Lodge 8 Dan Fox Dr Pittsfield MA Fully refundableReserve now, pay when you stay $121 nightly $136 total Mar 22 - Mar 23 Total with taxes and fees 9/10 Wonderful! (846 reviews) The suite was lovely.. staff was friendly.. out door hot tub we amazing after day of snowboarding. Rooms very clean Reviewed on Feb 17, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F22%2F2026&endDate=3%2F23%2F2026&selected=11449113&PinnedHotelID=11449113&HadPinnedHotel=true®ionId=9478) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG One West Street Pittsfield MA Fully refundable $103 nightly $115 total Feb 22 - Feb 23 Total with taxes and fees 8/10 Very Good! (1,005 reviews) Bathroom had somebody’s hair on the door and shower Reviewed on Feb 9, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%2F2026&selected=2067&PinnedHotelID=2067&HadPinnedHotel=true®ionId=9478) ![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel On North 297 North Street Pittsfield MA Fully refundableReserve now, pay when you stay $149 nightly $166 total Feb 22 - Feb 23 Total with taxes and fees 9.4/10 Exceptional! (824 reviews) Room was spotless, staff was amazing! Loved the bathroom setup! Will recommend and stay again! Reviewed on Feb 9, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%2F2026&selected=10246103&PinnedHotelID=10246103&HadPinnedHotel=true®ionId=9478) [See all 1,338 properties in Pittsfield](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F20%2F2026&endDate=2%2F21%2F2026®ionId=9478) 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. ## Find the Best Pittsfield Vacation Packages ## Pittsfield Essential Information | Language | English | | --------------- | ---------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Population | 43,300 | | Max Temp Winter | 30ºF | | Max Temp Summer | 75ºF | | Top Sights | [Bousquet Ski Area](https://www.expedia.com/Bousquet-Ski-Area-Pittsfield.d553248621532665283.Vacation-Attraction), [Colonial Theater](https://www.expedia.com/Colonial-Theater-Pittsfield.d553248621532665289.Vacation-Attraction) and [Barrington Stage Company](https://www.expedia.com/Barrington-Stage-Company-Pittsfield.d553248621532665294.Vacation-Attraction) | ## 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