Title: Pittsfield Travel Guide: Best of Pittsfield, Massachusetts Travel 2026 | Expedia.co.uk [Hotels in Pittsfield](https://expedia.co.uk/Pittsfield-Hotels.d9478.Travel-Guide-Hotels)[Holiday Rentals in Pittsfield](https://expedia.co.uk/Pittsfield-Holiday-Rentals.d9478.Travel-Guide-HolidayRentals)[Flights to Pittsfield](https://expedia.co.uk/Cheap-Flights-To-Pittsfield.d9478.Travel-Guide-Flights)[Pittsfield Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Pittsfield.d9478.Car-Hire-Guide)[Pittsfield Holidays](https://expedia.co.uk/Pittsfield.d9478.Holidays-City-Breaks) # Pittsfield Travel Guide ## Tourist Guide ![Pittsfield which includes a city](https://images.trvl-media.com/place/9478/5d9f4527-2b11-4f19-a1cd-36a7128d1304.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Pittsfield which includes a city](https://images.trvl-media.com/place/9478/5d9f4527-2b11-4f19-a1cd-36a7128d1304.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Pittsfield showing heritage elements and flowers](https://images.trvl-media.com/place/9478/c03d6c0a-571e-4d8d-97ce-2a52e7ae008d.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Pittsfield](https://images.trvl-media.com/place/9478/f051d8ab-a374-4061-85bd-408632dffc74.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Pittsfield showing a church or cathedral](https://images.trvl-media.com/place/9478/342acc42-6bf5-45ae-b31a-be5d01661040.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Pittsfield Things to do Reviews #### Located at a fork in the Housatonic River, this city provides an appealing mix of cultural diversions and outdoor pursuits. The largest town in the Berkshires region, Pittsfield has varied shops, services and restaurants, making it a great jumping-off point for hiking and camping trips to the nearby Pittsfield State Forest. There is much to explore within Pittsfield itself. Check out colourful street art, discover museum exhibits and attend performances in one of its cultural venues. Pittsfield was settled in the mid-18th century after a wealthy Bostonian purchased the land as a speculative investment. The village slowly grew in size during the 1800s and 1900s as wool and electrical manufacturing industries flourished. Get a taste of local history at the Berkshire Museum, one of the main tourist draws. A small museum with eclectic exhibits focusing on art, history and nature, it also has an interactive aquarium and hands-on activities for kids to enjoy. In downtown Pittsfield, enjoy Artscape, a self-guided walking tour of the city’s street art. Take a guided tour of Herman Melville's Arrowhead, the lovingly maintained former residence ofHerman Melville, who wrote his famous novel *Moby Dick* here in Pittsfield. In the evenings enjoy culture with a classical or contemporary professional ballet performance at the Albany Berkshire Ballet. Investigate the Colonial Theatre, a gilded old theatre that has been fully restored and offers an entertaining programme including music and theatrical performances. The Pittsfield Visitors Centre is found in the theatre’s lobby. In summer, make a splash at the area’s numerous lakes, which have plentiful opportunities for swimming, fishing and boating. As well as hiking through the forest, find year-round recreation available at the Bousquet Ski Resort and Family Fun Centre. Stop at the complex outside of ski season to enjoy the water park and go-karting track, perfect for summer fun. Drive to Pittsfield or use Amtrak's Lakeshore Limited rail service, which operates daily between Boston and Chicago. Pittsfield is also served by intercity bus lines from Boston, New York and Albany. ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-uk-fr-de.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Holiday Sale Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save. [Book now](https://expedia.co.uk/cheap-deals?rfrr=DX_SPRING_PROMO_9478) - Top hotels in Pittsfield - Top Holiday Rentals in Pittsfield ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Berkshire Mountain Lodge 8 Dan Fox Dr Pittsfield MA £105 1 Apr - 2 Apr includes taxes & fees Stay at this golf lodge in Pittsfield. Enjoy free Wi-Fi, free parking and a business centre. Our guests praise the helpful staff and the clean rooms in their ... 9/10 Wonderful! (870 reviews) This was great. I did not really need the kitchen for my stay but for future planning this wil be great! Plenty of room in the living area. Bed was comfortable. Just beautiful Reviewed on 9 Mar 2026 [](https://expedia.co.uk/Hotel-Search?startDate=01%2F04%2F2026&endDate=02%2F04%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 £106 31 Mar - 1 Apr includes taxes & fees Stay at this business-friendly hotel in Pittsfield. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ... 8/10 Very Good! (1,006 reviews) Hotel is going through a renovation which makes the place a little rougher than it’s used to be. No parking or limited parking at entrance of hotel. Valet parking personnel were parking cars on entrance round entrance and in the mourning, they were towing those cars from the property. Not a good ... Reviewed on 8 Mar 2026 [](https://expedia.co.uk/Hotel-Search?startDate=31%2F03%2F2026&endDate=01%2F04%2F2026&selected=2067&PinnedHotelID=2067&HadPinnedHotel=true®ionId=9478) ![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/ef3ce5c5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel On North 297 North Street Pittsfield MA £124 11 Mar - 12 Mar includes taxes & fees Stay at this business-friendly hotel in Pittsfield. Enjoy free Wi-Fi, free parking and room service. Our guests praise the helpful staff and the clean rooms ... 9.6/10 Exceptional! (830 reviews) Great one night experience, hotel was quiet and clean. Room was cozy and comfortable as well. Rate was very reasonable to make for a affordable ski trip Reviewed on 8 Mar 2026 [](https://expedia.co.uk/Hotel-Search?startDate=11%2F03%2F2026&endDate=12%2F03%2F2026&selected=10246103&PinnedHotelID=10246103&HadPinnedHotel=true®ionId=9478) [See all 1,344 properties in Pittsfield](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=11%2F03%2F2026&endDate=12%2F03%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. ![Hancock Village Inn Near Jiminy Peak](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/c8837e7e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hancock Village Inn Near Jiminy Peak Hancock MA Stay at this family-friendly holiday home in Pittsfield. Enjoy free Wi-Fi, laundry facilities and a pool table. Popular attractions Jiminy Peak Mountain Resort ... 10/10 Exceptional! (19 reviews) Really great host - communication was great. House is so close to skiing, can’t beat it Reviewed on 24 Feb 2026 [](https://expedia.co.uk/Pittsfield-Hotels-Hancock-Village-Inn-At-Jiminy-Peak.h89806253.Hotel-Information) ![A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything](https://images.trvl-media.com/lodging/20000000/19680000/19674700/19674617/7d88d05c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything Pittsfield MA Stay at this cabin in Pittsfield. Enjoy free Wi-Fi, a fitness centre and laundry facilities. Popular attractions Jiminy Peak Mountain Resort and Crane Museum ... 10/10 Exceptional! (129 reviews) The cabin was perfectly located for a week of exploring the Berkshires and southern Vermont. It is centrally located in the region, but feels private because it is surrounded by trees and set back from the road. It was the best stocked kitchen I've had in a rental. Relaxing by the pond was very peaceful; ... Reviewed on 30 Sept 2025 [](https://expedia.co.uk/Pittsfield-Hotels-A-Beautiful-Log-Cabin-In-The-Woods.h19674617.Hotel-Information) ![Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table](https://images.trvl-media.com/lodging/34000000/33500000/33492300/33492239/2ddd9b8b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table Pittsfield MA Stay at this family-friendly holiday home in Pittsfield. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Jiminy Peak Mountain Resort and ... 9.8/10 Exceptional! (154 reviews) This was a terrific place for our annual friend gathering! Plenty of comfortable beds for everyone! There were a couple of times we needed to reach out to the host and we’re grateful for a quick responses to our inquiries. We would highly recommend this place to others. Reviewed on 16 Feb 2026 [](https://expedia.co.uk/Pittsfield-Hotels-Beautiful-8-Bedroom.h33492239.Hotel-Information) [See all properties in Pittsfield](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=9478&sort=VACATION_RENTAL) 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. ## Check Pittsfield hotel availability [Tonight ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=9478&startDate=2026-03-10&endDate=2026-03-11)[10 Mar - 11 Mar](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=9478&startDate=2026-03-10&endDate=2026-03-11) [Tomorrow night ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=9478&startDate=2026-03-11&endDate=2026-03-12)[11 Mar - 12 Mar](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=9478&startDate=2026-03-11&endDate=2026-03-12) [This weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=9478&startDate=13%2F03%2F2026&endDate=15%2F03%2F2026)[13 Mar - 15 Mar](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=9478&startDate=13%2F03%2F2026&endDate=15%2F03%2F2026) [Next weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=9478&startDate=20%2F03%2F2026&endDate=22%2F03%2F2026)[20 Mar - 22 Mar](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=9478&startDate=20%2F03%2F2026&endDate=22%2F03%2F2026) ### Popular places to visit ![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.co.uk/Bousquet-Ski-Area-Pittsfield.d553248621532665283.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 5/5(2 reviews) You can browse the exhibits at Hancock Shaker Village, a museum with a story of its own, during your travels to Pittsfield. Wander the lakeside in this quaint area. [](https://expedia.co.uk/Hancock-Shaker-Village-Pittsfield.d6091849.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 studying the exhibits at Berkshire Museum in Pittsfield. Wander the lakeside in this family-friendly area. [](https://expedia.co.uk/Berkshire-Museum-Pittsfield.d553248621532665288.Attraction) #### Colonial Theater You can make plans for a show at Colonial Theater on your trip to Pittsfield. Wander the lakeside in this family-friendly area. [](https://expedia.co.uk/Colonial-Theater-Pittsfield.d553248621532665289.Attraction) #### Pittsfield Dog Park After visiting Pittsfield Dog Park, make a plan to see the other sights and activities in Pittsfield. Experience the area's entertainment venues or attend a sporting event. [](https://expedia.co.uk/Pittsfield-Dog-Park-Pittsfield.d906147467257606144.Attraction) #### Berkshire Community College Explore the campus of Berkshire Community College during your stay in Pittsfield. Experience the area's entertainment venues or attend a sporting event. [](https://expedia.co.uk/Berkshire-Community-College-Pittsfield.d876922321408139264.Attraction) ## Reviews of Pittsfield 4 Top destination 5 - Excellent 0 4 - Good 1 3 - Okay 0 2 - Disappointing 0 1 - Terrible 0 ### 4/5 - Good Verified traveller Visited Soda Chef for breakfast - recommend the pancakes and the owners are very welcoming ## Cities near Pittsfield ![Williamstown featuring café lifestyle](https://images.trvl-media.com/place/7859/20112747-2c45-42f7-89fe-e3ed195e2395.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Williamstown ![Lenox featuring an administrative building](https://images.trvl-media.com/place/8587/a35ecb1d-29c1-44ed-9d74-ab0562300a50.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Lenox ![Hancock showing a small town or village and tranquil scenes](https://images.trvl-media.com/place/112303/db340024-cf82-4278-bdad-f4da564f91cf.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Hancock ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - 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[Car hire near Pittsfield State Forest ](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Pittsfield-State-Forest.d6339854.Car-Hire-Guide) - [Car hire Stockbridge ](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Stockbridge.d162575.Car-Hire-Guide) - [Becket Holiday Rentals ](https://www.expedia.co.uk/Becket-Holiday-Rentals.d6005395.Travel-Guide-HolidayRentals) - [Lee Holiday Rentals ](https://www.expedia.co.uk/Lee-Holiday-Rentals.d8572.Travel-Guide-HolidayRentals) - [Peru Holiday Rentals ](https://www.expedia.co.uk/Peru-Holiday-Rentals.d553248634999167831.Travel-Guide-HolidayRentals) - [Richmond Holiday Rentals ](https://www.expedia.co.uk/Richmond-Holiday-Rentals.d151138.Travel-Guide-HolidayRentals) - [Stockbridge Holiday Rentals ](https://www.expedia.co.uk/Stockbridge-Holiday-Rentals.d162575.Travel-Guide-HolidayRentals) - Cities near Pittsfield - Places of interest [Williamstown](https://expedia.co.uk/Williamstown.dx7859)[Lenox](https://expedia.co.uk/Lenox.dx8587)[Hancock](https://expedia.co.uk/Hancock.dx112303) - [Tanglewood Music Center ](https://expedia.co.uk/Tanglewood-Music-Center-Lenox.d503292.Attraction) - [Williams College ](https://expedia.co.uk/Williams-College-Williamstown.d6091833.Attraction) - [Green Mountain National Forest ](https://expedia.co.uk/Green-Mountain-National-Forest-Vermont.d6115904.Attraction) - [Norman Rockwell Museum ](https://expedia.co.uk/Norman-Rockwell-Museum-Stockbridge.d6091839.Attraction) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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