Title: Pittsfield Vacation Packages 2026 from $364 | 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 $364 ## 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 Clocktower Hotel at Century House, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/20000/15200/15101/0ae7a345_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Clocktower Hotel at Century House, an Ascend Collection Hotel $364 per person Mar 13 - Mar 16 found 1 day ago Roundtrip flight included Fort Lauderdale (FLL) to Albany (ALB) 8.4/10 Very Good! (1,004 reviews) Nice warm pool. Clean room, great service Reviewed on Jan 31, 2026 ![The Landing Hotel at Rivers Casino & Resort](https://images.trvl-media.com/lodging/20000000/19100000/19093300/19093277/146e5c0f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Landing Hotel at Rivers Casino & Resort Nothside $414 per person Mar 13 - Mar 16 found 1 day ago Roundtrip flight included Fort Lauderdale (FLL) to Albany (ALB) 9.2/10 Wonderful! (1,005 reviews) The rooms were very nice. The hotel overall was quiet and clean Reviewed on Jan 27, 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 $668 per person Apr 2 - Apr 5 found 1 day ago Roundtrip non-stop flight included San Juan (SJU) to Albany (ALB) 9.2/10 Wonderful! (1,001 reviews) Great staff, clean rooms Reviewed on Jan 31, 2026 ![Hampton Inn Albany-Wolf Road (Airport)](https://images.trvl-media.com/lodging/1000000/10000/700/698/61f54404_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hampton Inn Albany-Wolf Road (Airport) $380 per person Mar 13 - Mar 16 found 1 day ago Roundtrip flight included Fort Lauderdale (FLL) to Albany (ALB) 8.8/10 Excellent! (1,001 reviews) Nice staff, clean room Reviewed on Feb 3, 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 $480 per person Mar 13 - Mar 16 found 1 day ago Roundtrip flight included Fort Lauderdale (FLL) 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/2026-03-05/2026-03-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=ALB&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### 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 8 - Mar 9 Total with taxes and fees 9/10 Wonderful! (826 reviews) Room was clean and nicely equipped with kitchen. Will return if the future. Reviewed on Feb 1, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F8%2F2026&endDate=3%2F9%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! (1,001 reviews) generally good Reviewed on Jan 19, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F7%2F2026&endDate=3%2F8%2F2026&selected=2067&PinnedHotelID=2067&HadPinnedHotel=true®ionId=9478) ![Best Western Plus Berkshire Hills Inn & Suites](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Plus Berkshire Hills Inn & Suites 1350 W Housatonic St Pittsfield MA Fully refundableReserve now, pay when you stay $90 nightly $101 total Feb 8 - Feb 9 Total with taxes and fees 8.4/10 Very Good! (1,000 reviews) Great place, room was clean and spacious. Breakfast time could last a little longer though, ending time was 9:30am, maybe extending until 11am is best. But overall was great. Reviewed on Jan 20, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F8%2F2026&endDate=2%2F9%2F2026&selected=789964&PinnedHotelID=789964&HadPinnedHotel=true®ionId=9478) [See all 1,336 properties in Pittsfield](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F6%2F2026&endDate=2%2F7%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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- [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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