Title: The Best Pittsfield, MA Chalets from $1,585 | 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)[Pittsfield Vacation Packages](https://expedia.com/Pittsfield.d9478.Destination-Travel-Guides) ![Pittsfield featuring a city](https://images.trvl-media.com/place/9478/b5f5430c-dc51-405d-9103-478c33e1bf14.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/9478/b5f5430c-dc51-405d-9103-478c33e1bf14.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=9478&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=9478&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=9478&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=9478&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Pittsfield chalets ![Terrace/patio](https://images.trvl-media.com/lodging/124000000/123360000/123354300/123354233/225c30fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/124000000/123360000/123354300/123354233/3201c410.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123360000/123354300/123354233/c8edb36b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123360000/123354300/123354233/ba39107a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike [](https://www.expedia.com/Charlemont-Hotels-Joia-Verde-ChaletSleeps-8.h123354233.Hotel-Information) Charlemont 10/10 Exceptional (1 review) $599 nightly $669 total Feb 24 - Feb 25 Total with taxes and fees [](https://www.expedia.com/Charlemont-Hotels-Joia-Verde-ChaletSleeps-8.h123354233.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/111000000/110260000/110251200/110251122/84aaf038.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/111000000/110260000/110251200/110251122/w1200h799x0y1-17216d72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110260000/110251200/110251122/b9f89b31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/111000000/110260000/110251200/110251122/8836ff52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Secluded Luxurious Chalet with Pool and Hot Tub. Pet-Friendly! [](https://www.expedia.com/Cropseyville-Hotels-Sleeps-16-Hot-Tub-Private-Heated-Pool-Fire-Pit-Game-Room.h110251122.Hotel-Information) Cropseyville 10/10 Exceptional (3 reviews) "Wonderful home and property. Stayed for a family wedding weekend. The home, hot tub and pool were a perfect way to relax before and after the ceremony." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patrick H. $1,428 nightly $1,585 total Feb 16 - Feb 17 Total with taxes and fees [](https://www.expedia.com/Cropseyville-Hotels-Sleeps-16-Hot-Tub-Private-Heated-Pool-Fire-Pit-Game-Room.h110251122.Hotel-Information) 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. [View all properties](https://expedia.com/Hotel-Search?startDate=2026-02-25&endDate=2026-02-26®ionId=9478&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America®ionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&lodging=CABIN) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America®ionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&lodging=VACATION_HOME) Cottages [](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America®ionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&lodging=COTTAGE) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America®ionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&lodging=APART_HOTEL) Apartments [](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America®ionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&lodging=APARTMENT) Condos [](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America®ionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&lodging=CONDO) Chalets [](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America®ionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&lodging=CHALET) Villas [](https://www.expedia.com/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America®ionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&lodging=VILLA) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Chalets.d9478-aaChalets.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Chalets.d9478-aaChalets.Travel-Guide-Accommodation) ## Top Pittsfield Hotel Reviews ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Perfect location, big rooms, nice staff. " [](https://expedia.com/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "Room was spotless, staff was amazing! Loved the bathroom setup! Will recommend and stay again! " [](https://expedia.com/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "The staff was wonderful " [](https://expedia.com/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg) ### The Williams Inn 10/10 Excellent "A beautiful hotel to stay at while visiting the Williams campus. Our room had a nice view of the woods. Rooms were clean and with comfortable beds. The common areas of the hotel were beautiful and cozy with the fireplaces going. Easy check in and out with friendly staff." [](https://expedia.com/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "The staff is very helpful, and always willing to assist with any inquiries. The room was definitely clean and well-stocked throughout our entire stay." [](https://expedia.com/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "Spacious 2 bed 2 bath!" [](https://expedia.com/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 10/10 Excellent "loved " [](https://expedia.com/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg) ### Hotel Downstreet, an Ascend Collection Hotel 10/10 Excellent "Room was cozy and clean. Staff was very responsive and courteous. The entire place was great from location to feel." [](https://expedia.com/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![Comfort Inn & Suites East Greenbush - Albany](https://images.trvl-media.com/lodging/2000000/1060000/1052400/1052319/ea181a79_y.jpg) ### Comfort Inn & Suites East Greenbush - Albany 10/10 Excellent "Quiet, clean," [](https://expedia.com/Albany-Hotels-Comfort-Inn-Suites-East-Greenbush-Albany.h1052319.Hotel-Information) ## Find out more about Pittsfield ## Pittsfield Chalets information | Number of reviews | 3 | | ----------------- | --------- | | Accommodation | 6 Chalets | | Lowest Price | $1,585 | | Highest Price | $1,585 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [Cabin Rentals in Berkshire County ](https://www.expedia.com/Berkshire-County-Cabins.d553248635083901436-aaCabins.Travel-Guide-Accommodation) - [Hotels near Berkshire Museum ](https://www.expedia.com/Berkshire-Museum-Hotels.0-l553248621532665288-0.Travel-Guide-Filter-Hotels) - [Hotels near Berkshire Athenaeum ](https://www.expedia.com/Berkshire-Athenaeum-Hotels.0-l553248621532665287-0.Travel-Guide-Filter-Hotels) - [Hotels near Colonial Theater ](https://www.expedia.com/Colonial-Theater-Hotels.0-l553248621532665289-0.Travel-Guide-Filter-Hotels) - [Hotels near Barrington Stage Company ](https://www.expedia.com/Barrington-Stage-Company-Hotels.0-l553248621532665294-0.Travel-Guide-Filter-Hotels) - [Hotels near Crane Museum of Papermaking ](https://www.expedia.com/Crane-Museum-Of-Papermaking-Hotels.0-l553248621533116687-0.Travel-Guide-Filter-Hotels) - [Hotels near Pittsfield Station ](https://www.expedia.com/Pittsfield-Station-Hotels.d6195403.Travel-Guide-Hotels) - [Hotels near Canoe Meadows Wildlife Sanctuary ](https://www.expedia.com/Canoe-Meadows-Wildlife-Sanctuary-Hotels.0-l553248621532665285-0.Travel-Guide-Filter-Hotels) - [Hotels near Herman Melville's Arrowhead ](https://www.expedia.com/Herman-Melvilles-Arrowhead-Hotels.0-l553248621532665284-0.Travel-Guide-Filter-Hotels) - [Hotels near Pittsfield Municipal ](https://www.expedia.com/Pittsfield-Municipal-Airport-Hotels.0-aPSF-0.Travel-Guide-Filter-Hotels) - [Flights to Berkshire County ](https://www.expedia.com/Destinations-In-Berkshire-County.d553248635083901436.Flight-Destinations) - [Flights from Pittsfield Municipal ](https://www.expedia.com/lp/airports/psf/flights-from-pittsfield-municipal-airport) - [Flights from Albany (ALB) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/alb/psf/albany-to-pittsfield) - [Flights from Boston (BOS) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/bos/psf/boston-to-pittsfield) - [Flights from New York (NYC) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/nyc/psf/new-york-to-pittsfield) - [Flights from Worcester (ORH) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/orh/psf/worcester-to-pittsfield) - [Flights from Pittsburgh (PIT) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/pit/psf/pittsburgh-to-pittsfield) - [Flights from Philadelphia (PHL) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/phl/psf/philadelphia-to-pittsfield) - [Flights from Charlotte (CLT) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/clt/psf/charlotte-to-pittsfield) - [Flights from Orlando (MCO) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/mco/psf/orlando-to-pittsfield) - [Flights from Dallas (DFW) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/dfw/psf/dallas-to-pittsfield) - [Flights from Fort Lauderdale (FLL) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/fll/psf/fort-lauderdale-to-pittsfield) - [Flights from New York (JFK) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/jfk/psf/new-york-to-pittsfield) - [Flights from Washington (DCA) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/dca/psf/washington-to-pittsfield) - [Flights from Tampa (TPA) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/tpa/psf/tampa-to-pittsfield) - [Flights from Los Angeles (LAX) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/lax/psf/los-angeles-to-pittsfield) - [Flights from New York (LGA) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/lga/psf/new-york-to-pittsfield) - [Flights from Atlanta (ATL) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/atl/psf/atlanta-to-pittsfield) - [Flights from Islip (ISP) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/isp/psf/islip-to-pittsfield) - [Flights from Chicago (ORD) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/ord/psf/chicago-to-pittsfield) - [Flights from Denver (DEN) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/den/psf/denver-to-pittsfield) - [Flights from San Francisco (SFO) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/sfo/psf/san-francisco-to-pittsfield) - [Flights from Hartford (BDL) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/bdl/psf/hartford-to-pittsfield) - [Flights from Baltimore (BWI) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/bwi/psf/baltimore-to-pittsfield) - [Flights from Detroit (DTW) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/dtw/psf/detroit-to-pittsfield) - [Flights from Raleigh (RDU) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/rdu/psf/raleigh-to-pittsfield) - [Flights from Houston (IAH) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/iah/psf/houston-to-pittsfield) - [Flights from Rochester (ROC) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/roc/psf/rochester-to-pittsfield) - [Flights from Kansas City (MCI) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/mci/psf/kansas-city-to-pittsfield) - [Flights from Miami (MIA) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/mia/psf/miami-to-pittsfield) - [Flights from Sarasota (SRQ) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/srq/psf/sarasota-to-pittsfield) - [Flights from Providence (PVD) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/pvd/psf/providence-to-pittsfield) - [Flights from Buffalo (BUF) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/buf/psf/buffalo-to-pittsfield) - [Flights from St. Louis (STL) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/stl/psf/st-louis-to-pittsfield) - [Flights from Minneapolis (MSP) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/msp/psf/minneapolis-to-pittsfield) - [Flights to Pittsfield Municipal ](https://www.expedia.com/Cheap-Flights-To-Pittsfield-Municipal.d6031274.Travel-Guide-Flights) - [Flights from Columbus (CMH) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/cmh/psf/columbus-to-pittsfield) - [Flights from Indianapolis (IND) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/ind/psf/indianapolis-to-pittsfield) - [Flights from West Palm Beach (PBI) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/pbi/psf/west-palm-beach-to-pittsfield) - [Flights from Phoenix (PHX) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/phx/psf/phoenix-to-pittsfield) - [Flights from Allentown (ABE) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/abe/psf/allentown-to-pittsfield) - [Flights from Seattle (SEA) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/sea/psf/seattle-to-pittsfield) - [Flights from Wilmington (ILM) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/ilm/psf/wilmington-to-pittsfield) - [Flights from White Plains (HPN) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/hpn/psf/white-plains-to-pittsfield) - [Flights from Greenville (GSP) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/gsp/psf/greenville-to-pittsfield) - [Flights from Milwaukee (MKE) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/mke/psf/milwaukee-to-pittsfield) - [Flights from Portland (PDX) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/pdx/psf/portland-to-pittsfield) - [Flights from Toronto (YYZ) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/yyz/psf/toronto-to-pittsfield) - [Flights from Montreal (YUL) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/yul/psf/montreal-to-pittsfield) - [Flights from Memphis (MEM) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/mem/psf/memphis-to-pittsfield) - [Flights from Las Vegas (LAS) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/las/psf/las-vegas-to-pittsfield) - [Flights from Charleston (CHS) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/chs/psf/charleston-to-pittsfield) - [Flights from Madison (MSN) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/msn/psf/madison-to-pittsfield) - [Flights from Norfolk (ORF) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/orf/psf/norfolk-to-pittsfield) - [Flights from Richmond (RIC) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/ric/psf/richmond-to-pittsfield) - [Flights from Ontario (ONT) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/ont/psf/ontario-to-pittsfield) - [Flights from Pensacola (PNS) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/pns/psf/pensacola-to-pittsfield) - [Flights from Fargo (FAR) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/far/psf/fargo-to-pittsfield) - [Flights from Cincinnati (CVG) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/cvg/psf/cincinnati-to-pittsfield) - [Flights from Burlington (BTV) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/btv/psf/burlington-to-pittsfield) - [Flights from New Haven (HVN) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/hvn/psf/new-haven-to-pittsfield) - [Hopscotch Air Nantucket (ACK) to Pittsfield (PSF) flights ](https://www.expedia.com/lp/flight-routes/hopscotch-air-from-nantucket-memorial-to-pittsfield-municipal/o2/ack/psf) - [Flights from Tucson (TUS) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/tus/psf/tucson-to-pittsfield) - [Hopscotch Air Burbank (BUR) to Pittsfield (PSF) flights ](https://www.expedia.com/lp/flight-routes/hopscotch-air-from-hollywood-burbank-to-pittsfield-municipal/o2/bur/psf) - [Flights from Louisville (SDF) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/sdf/psf/louisville-to-pittsfield) - [Flights from Newburgh (SWF) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/swf/psf/newburgh-to-pittsfield) - [Flights from Reno (RNO) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/rno/psf/reno-to-pittsfield) - [Flights from Barcelona (BCN) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/bcn/psf/barcelona-to-pittsfield) - [Flights from Des Moines (DSM) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/dsm/psf/des-moines-to-pittsfield) - [Flights from Kuwait City (KWI) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/kwi/psf/kuwait-city-to-pittsfield) - [Flights from Charlottesville (CHO) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/cho/psf/charlottesville-to-pittsfield) - [Flights from Binghamton (BGM) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/bgm/psf/binghamton-to-pittsfield) - [Flights from San Jose (SJC) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/sjc/psf/san-jose-to-pittsfield) - [Flights from El Paso (ELP) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/elp/psf/el-paso-to-pittsfield) - [Flights from London (LHR) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/lhr/psf/london-to-pittsfield) - [Flights from Hyannis (HYA) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/hya/psf/hyannis-to-pittsfield) - [Flights from Fort Myers (RSW) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/rsw/psf/fort-myers-to-pittsfield) - [Flights from Ithaca (ITH) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/ith/psf/ithaca-to-pittsfield) - [Flights from St. Petersburg (PIE) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/pie/psf/st-petersburg-to-pittsfield) - [Flights from San Diego (MYF) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/myf/psf/san-diego-to-pittsfield) - [Flights from Cancun (CUN) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/cun/psf/cancun-to-pittsfield) - [Flights from Savannah (SAV) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/sav/psf/savannah-to-pittsfield) - [Flights from Greensboro (GSO) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/gso/psf/greensboro-to-pittsfield) - [Flights from Düsseldorf (DUS) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/dus/psf/dusseldorf-to-pittsfield) - [Flights from Panama City (ECP) to Pittsfield (PSF) ](https://www.expedia.com/lp/flights/ecp/psf/panama-city-to-pittsfield) - [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) - [Car rental Pittsfield Airport (PSF) ](https://www.expedia.com/Car-Rentals-In-Pittsfield-Municipal.d6031274.Car-Rental-Guide)