Title: Pittsfield Vacation Packages 2026 from $522 | 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 from $522 ## 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. ## The Latest Pittsfield vacation packages Price found within the past 48 hours. Click for updated prices. ![The Manchester View](https://images.trvl-media.com/lodging/7000000/6850000/6846700/6846625/b534a8c8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Manchester View $522 per person May 4 - May 7 found 18 hours ago Roundtrip non-stop flight included New York (JFK) to Albany (ALB) 9.4/10 Exceptional! (772 reviews) The MV was perfect for a getaway to the southern greens for snow. Place was clean, great water pressure, and heat. Had to upgrade my room and it wasn't a problem. Looking forward to coming back. Reviewed on Jan 28, 2026 ![Saratoga Casino Hotel](https://images.trvl-media.com/lodging/15000000/14720000/14710900/14710814/991e526b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Saratoga Casino Hotel $625 per person Mar 19 - Mar 23 found 2 hours ago Roundtrip non-stop flight included San Juan (SJU) to Albany (ALB) 9.2/10 Wonderful! (1,001 reviews) The staff and room, wonderful great stay. Reviewed on Feb 11, 2026 ![The Equinox Golf Resort & Spa](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/0d30b96a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Equinox Golf Resort & Spa Manchester Village Historic District $524 per person May 4 - May 7 found 17 hours ago Roundtrip non-stop flight included New York (JFK) to Albany (ALB) 7.4/10 Good! (567 reviews) We have been staying at the Equinox for over 35 yrs. Love the whole scene and vibe. Love the pool and hot tub. Love the big real wood fireplace. Reviewed on Jan 24, 2026 ![Comfort Inn & Suites Schenectady - Scotia](https://images.trvl-media.com/lodging/27000000/26940000/26937300/26937215/7d6766cd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Comfort Inn & Suites Schenectady - Scotia Scotia $603 per person Mar 19 - Mar 23 found 2 hours ago Roundtrip non-stop flight included San Juan (SJU) to Albany (ALB) 9.4/10 Exceptional! (822 reviews) Staff were friendly and helpful. The place was very clean. Pool/hot tub/ sauna were also very clean and in good condition. Reviewed on Feb 11, 2026 ![Hilton Albany](https://images.trvl-media.com/lodging/1000000/430000/424500/424407/b38d0fca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Albany Downtown Albany $638 per person Mar 24 - Mar 26 found 1 day ago Roundtrip flight included New York (NYC) to Albany (ALB) 7/10 Good! (1,002 reviews) The room was clean, beds comfortable; the shower gel was out in the shower. The customer service was excellent. Staff was so helpful in getting all needs met! The continental breakfast was superb! Our waitresses were excellent, & friendly! Reviewed on Feb 1, 2026 Don't see what you're looking for? See all available trips from Columbus to Pittsfield [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-12/2026-03-19/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=ALB&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](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 4/5(9 reviews) 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 4.5/5(53 reviews) 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 15 - Mar 16 Total with taxes and fees 9/10 Wonderful! (838 reviews) Perfect location, big rooms, nice staff. Reviewed on Feb 10, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F15%2F2026&endDate=3%2F16%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 $102 nightly $114 total Mar 7 - Mar 8 Total with taxes and fees 8/10 Very Good! (1,004 reviews) The staff was wonderful Reviewed on Feb 8, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F7%2F2026&endDate=3%2F8%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 18 - Feb 19 Total with taxes and fees 9.4/10 Exceptional! (823 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%2F18%2F2026&endDate=2%2F19%2F2026&selected=10246103&PinnedHotelID=10246103&HadPinnedHotel=true®ionId=9478) [See all 1,343 properties in Pittsfield](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F13%2F2026&endDate=2%2F14%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) | ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf 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![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Pittsfield vacation package cost? ### What are the cheapest months to go to Pittsfield? ### How many days is enough for Pittsfield? ### Is it worth booking a vacation package to Pittsfield? ### How to find the best Pittsfield package deals? ### Is it cheaper to book a Pittsfield vacation as a package? ### When to book a vacation package to Pittsfield? ### Does Expedia offer Book Now, Pay Later Pittsfield vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [Hotels near Berkshire Museum 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- [Berkshire Museum ](https://www.expedia.com/Berkshire-Museum-Pittsfield.d553248621532665288.Vacation-Attraction) - [Berkshire Athenaeum ](https://www.expedia.com/Berkshire-Athenaeum-Pittsfield.d553248621532665287.Vacation-Attraction) - [Canoe Meadows Wildlife Sanctuary ](https://www.expedia.com/Canoe-Meadows-Wildlife-Sanctuary-Pittsfield.d553248621532665285.Vacation-Attraction) - [Herman Melville's Arrowhead ](https://www.expedia.com/Herman-Melvilles-Arrowhead-Pittsfield.d553248621532665284.Vacation-Attraction) - [Bousquet Ski Area ](https://www.expedia.com/Bousquet-Ski-Area-Pittsfield.d553248621532665283.Vacation-Attraction) - [Guido's Marketplace ](https://www.expedia.com/Guidos-Marketplace-Pittsfield.d553248621532665282.Vacation-Attraction) - [Car rental Pittsfield Airport (PSF) ](https://www.expedia.com/Car-Rentals-In-Pittsfield-Municipal.d6031274.Car-Rental-Guide) \* Savings based on package bookings compared to the price of the same components booked separately. 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