Title: Book the Best Pittsfield Hotels with FREE PARKING in 2025 | Expedia.ca [Hotels in Pittsfield](https://expedia.ca/Pittsfield-Hotels.d9478.Travel-Guide-Hotels)[Vacation Rentals in Pittsfield](https://expedia.ca/Pittsfield-Vacation-Rentals.d9478.Travel-Guide-VacationRentals)[Flights to Pittsfield](https://expedia.ca/Cheap-Flights-To-Pittsfield.d9478.Travel-Guide-Flights)[Pittsfield Car Rentals](https://expedia.ca/Car-Rentals-In-Pittsfield.d9478.Car-Rental-Guide)[Pittsfield Vacation Packages](https://expedia.ca/Pittsfield.d9478.Destination-Travel-Guides) ![Pittsfield which includes flowers and heritage elements](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105629-Pittsfield.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with Free Parking in Pittsfield, MA from CA $93 ### Change your mind Book hotels with free cancellation ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ### Be picky Search almost a million properties worldwide ## Check availability on Pittsfield Hotels with Free Parking Tonight [Oct 6 - Oct 7](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-10-06&endDate=2025-10-07&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 7 - Oct 8](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-10-07&endDate=2025-10-08&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Pittsfield Hotels with Free Parking ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/eac89037.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/8666c376.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/90dd9d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Berkshire Hills Inn & Suites Pittsfield 8.6/10 Excellent (1000) "Great property would certainly stay again." CA $142 CA $158 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/5acdf3c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a25612d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/207845f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG Pittsfield 8.0/10 Very good (893) "Excellent customer service and great rooms" CA $144 CA $160 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/f450d89a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/670699cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/74865ec0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Mountain Lodge Pittsfield 9.0/10 Wonderful (677) "Very convenient set up of both room and kitchen, resort very easy to navigate. " CA $130 CA $176 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/fdeb3407.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe King Interior Suite- NO PETS ALLOWED](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/88509527.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch flat-screen TV with cable channels, TV, streaming services](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/d28e6aa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/c81c0732.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Central Downtown Inn & Suites Pittsfield 8.8/10 Excellent (321) "Nice place " CA $138 CA $154 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/9e766351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/c3ea2282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/651f878e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel On North Pittsfield 9.6/10 Exceptional (777) "Great property! Very large clean room in a unique hotel! " CA $170 CA $190 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/6a7ad915.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/a89bc327.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/67e1adab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/617da859.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG Pittsfield 9.4/10 Exceptional (51) "Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout" CA $177 CA $197 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/c3ce1b97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/3a99baa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/b4275c3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/8f954601.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Inn Pittsfield 7.8/10 Good (825) "Nicely remodeled " CA $103 CA $116 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Inn.h297173.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/5fa17ca2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/b6081d93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/507a7437.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/1715f4d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Lenox Pittsfield Pittsfield 9.2/10 Wonderful (647) "We always stay at the Garden Inn when visiting the Berkshires." CA $188 CA $210 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Pittsfield-Hotels-Hilton-Garden-Inn-Lenox-Pittsfield.h10246064.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/a38bbe4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/811d3663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/44aa4835.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/3fc8dc3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions! Pittsfield 8.0/10 Very good (5) "Very clean and spacious! We enjoyed our stay with our small pup!" CA $375 CA $687 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-Home-W-Lake-And-Mountain-Views-Near-Skiing.h106650307.Hotel-Information) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/abb5a87f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/c204d876.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/c2037034.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/3ed5d9ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### FairBridge Inn Express Pittsfield 5.4/10 (787) "Good service and people" CA $112 CA $125 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Pittsfield-Hotels-Econo-Lodge.h1543.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.ca/Hotel-Search?startDate=2025-10-21&endDate=2025-10-22®ionId=9478&adults=2&amenities=FREE_PARKING&sort=RECOMMENDED&openPlayBack=true) ## Top Pittsfield Hotel Reviews ![Berkshire Inn](//images.trvl-media.com/lodging/1000000/300000/297200/297173/c3ce1b97_y.jpg) ### Berkshire Inn 10/10 Excellent "Nicely remodeled " [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Inn.h297173.Hotel-Information) ![Comfort Inn & Suites East Greenbush - Albany](//images.trvl-media.com/lodging/2000000/1060000/1052400/1052319/ea181a79_y.jpg) ### Comfort Inn & Suites East Greenbush - Albany 10/10 Excellent "Check in was quick and welcoming. The room was just right for us; plenty of space, bed made for sleeping, temperature easily controlled. Breakfast offered a nice selection for those in a hurry to those who settled in for a chance to dill up for the day. " [](https://expedia.ca/Albany-Hotels-Comfort-Inn-Suites-East-Greenbush-Albany.h1052319.Hotel-Information) ![Best Western Plus Berkshire Hills Inn & Suites](//images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg) ### Best Western Plus Berkshire Hills Inn & Suites 10/10 Excellent "Clean place. Good breakfast and friendly staff" [](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![The Red Lion Inn](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "Great place! Food excellent ss well!" [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Vacation Village in the Berkshires](//images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "Great!" [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Hotel On North](//images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "There was construction noise next door." [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/30000/20500/20447/588051f1_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "The staff was helpful, friendly. Nice location. The room was very clean and quiet, but so much of the place is brown. Brown carpet, brown paneled walls, brown chair, brown furniture, brown lamps. A minor detraction, but I look at hotel decor with a discerning eye and I like things to be less bland/mundane." [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Hilton Garden Inn Lenox Pittsfield](//images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/5fa17ca2_y.jpg) ### Hilton Garden Inn Lenox Pittsfield 10/10 Excellent "Everything about room was good except shower area. Grout around shower floor was black and moldy." [](https://expedia.ca/Pittsfield-Hotels-Hilton-Garden-Inn-Lenox-Pittsfield.h10246064.Hotel-Information) ![The Central Downtown Inn & Suites](//images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/fdeb3407_y.jpg) ### The Central Downtown Inn & Suites 10/10 Excellent "All good. 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