Title: Pittsfield Vacation Packages 2026 from $580 | 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 $580 ## 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 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 $580 per person Mar 26 - Mar 29 found 1 day ago Roundtrip non-stop flight included New York (NYC) 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 ![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) $595 per person Apr 6 - Apr 13 found 1 day ago Roundtrip flight included New York (NYC) to Albany (ALB) 8.8/10 Excellent! (1,001 reviews) Room was clean. Only issue was when taking a shower the water didn’t drain. Reviewed on Feb 14, 2026 ![Hilton Garden Inn Albany Airport](https://images.trvl-media.com/lodging/1000000/110000/102000/101993/421d66bb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Garden Inn Albany Airport $740 per person Apr 6 - Apr 13 found 1 day ago Roundtrip flight included New York (NYC) to Albany (ALB) 8/10 Very Good! (1,214 reviews) Could use some updating Keurig coffee pot was finicky. Couldn’t get it to work some days. The water reservoir did not look clean little rusted areas in there. The creamer was spoiled. I had some issues with water dripping from the bottom of the little refrigerator areas inside were wet and you could tell they have been damaged by water in the past. I did have some plumbing issues with my tub took a shower. The water was up to my ankles, and the bottom of the tub just was not secured to whatever is underneath there. However, I did express that concern and maintenance took care of it. Overall served the purpose. It was quiet. It was nice to have the restaurant and bar downstairs. I do feel like it needs some updating and could be cleaner the rugs look like they need to be shampooed. They don’t look like they even get vacuumed. I thought it was removed, it’s just is an older hotel. I’m assuming. yes but before the price I expected a little bit more. Reviewed on Feb 17, 2026 ![Marriott Albany](https://images.trvl-media.com/lodging/1000000/20000/11000/10979/1856b3b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Marriott Albany $707 per person Apr 6 - Apr 13 found 1 day ago Roundtrip flight included New York (NYC) to Albany (ALB) 8.2/10 Very Good! (751 reviews) Room was clean Someone was smoking marijuana and the smell was a little bothering check-in. Staff was very friendly. The staff member today when I checked out, put me on hold when I called down and never answered the phone back and then when I did call back, put me on hold again, but all in all must stay was OK. Reviewed on Feb 15, 2026 ![Holiday Inn Express Hotel & Suites West Coxsackie by IHG](https://images.trvl-media.com/lodging/3000000/2600000/2591600/2591583/2081618e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Express Hotel & Suites West Coxsackie by IHG $626 per person Apr 6 - Apr 13 found 1 day ago Roundtrip flight included New York (NYC) to Albany (ALB) 8.4/10 Very Good! (971 reviews) This place would be 5 stars if someone hadn't smoked enough marijuana in the elevator and on our floor to stink up the entire floor. It was 1 day out of 4 that happened. Breakfast and room were great. Reviewed on Feb 13, 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/2026-03-18/2026-03-25/?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 $142 nightly $158 total Mar 20 - Mar 21 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%2F20%2F2026&endDate=3%2F21%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%2F19%2F2026&endDate=2%2F20%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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