Title: Book the Best HISTORIC Hotels in Pittsfield 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 Historic Hotels in Pittsfield, MA from CA $281 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Pittsfield Historic Hotels Tonight [Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-10-29&endDate=2025-10-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 30 - Oct 31](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-10-30&endDate=2025-10-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Pittsfield Historic Hotels ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d969459c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Queen Beds (Main Inn)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/5f2e6b29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Firehouse)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/71ef2331.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Red Lion Inn Stockbridge 8.8/10 Excellent (1022) "Picture perfect Inn" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jeff CA $195 CA $281 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w907h683x58y0-59aad182.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w510h683x258y0-04b5e846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, printers](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w919h683x60y0-f3238385.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w905h683x60y0-b01f3b74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### North Getaway Cottage Williamstown 9.4/10 Exceptional (23) "Claudia is such a considerate and thoughtful host! We felt so welcome and at ease." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Caroline J. CA $282 CA $621 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Williamstown-Hotels-Vacation-Getaway-Or-Remote-Workschool-Location.h60763766.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/9c846f70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/2a4ba750.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/a110f773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/w1008h683x16y0-72a8567d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn Hancock 10/10 Exceptional (23) "This property is spacious, clean and well- appointed. I would stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda M. CA $146 CA $329 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Hancock-Hotels-SKI-ONOFF-1BR-SUITE-1ST-FLR-SLEEPS-4-JIMINY-PEAK.h69787457.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=2025-11-12&endDate=2025-11-13®ionId=9478&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Pittsfield Hotel Reviews ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](//images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "Everything is clean " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.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 "I have stayed here many times and it is consistently a comfortable, clean and quiet place." [](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.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 "View of the lake was lovely! Breakfast was fine—yogurt, eggs, pancakes and cereal. Coffee was plentiful!" [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.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 "Parking very safe. Staff very friendly. Room spacious, clean and comfortable. Hotel appearance is elegant. Only a couple of issues on breakfast: you need hotter pork sausage and soft butter. Other than that is was nearly perfect." [](https://expedia.ca/Albany-Hotels-Comfort-Inn-Suites-East-Greenbush-Albany.h1052319.Hotel-Information) ![Quality Inn](//images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg) ### Quality Inn 10/10 Excellent "Clean and convenient. Great front desk help. " [](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ![Hotel On North](//images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "Clean room, great location. Restaurant phenomenal " [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![Hotel Downstreet, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg) ### Hotel Downstreet, an Ascend Collection Hotel 10/10 Excellent "Good value. A good place." [](https://expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![Berkshire Inn](//images.trvl-media.com/lodging/1000000/300000/297200/297173/c3ce1b97_y.jpg) ### Berkshire Inn 10/10 Excellent "This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again." [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Inn.h297173.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 "This is a historical hotel and indeed the history is fabulous, everything appears like it did in 1773. Trouble is the rooms are also like this and the beds felt like they were 200 years old - so very uncomfortable. All part of the experience. Our room faced the street and I was surprised how much traffic noise kept me up until late at night, next time I will request a room facing inward. Not enough staff at the bar and dining during peak weekends, took forever just to get a cup of hot chocolate for the kids. But, very quaint, beautiful, that Main Street is just classic. " [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ## Frequently asked questions ### What should a history enthusiast expect from a trip to Pittsfield? > The historical places in Pittsfield are probably at the top of your sightseeing list. During your visit, you can check out the local entertainment venues. ### How many historical hotels are there in Pittsfield? > In Pittsfield, there are 72 hotel accommodations bookable on Expedia though you won't find many designated historic hotels. ### What are the must-see historical places and other sights to visit in Pittsfield? > Pittsfield is notable for landmarks like Colonial Theater, Hancock Shaker Village, and Herman Melville's Arrowhead. Cultural venues include Berkshire Museum, Barrington Stage Company, and Crane Museum of Papermaking. A couple of additional sights to add to your agenda are Bousquet Ski Area and Housatonic River. ### What is a historic hotel like in Pittsfield? > When you book a historic hotel, you'll spend a night or two in a place that has an officially recognized historic designation. A stately home, palace or even a lodge, old police station, or skyscraper can be turned into a historic hotel as long as it's of special interest. Traditional architecture and period features are often preserved within the guestrooms or public spaces of historic hotels in Pittsfield, giving a historical feel. ### What is the difference between a historic hotel and a heritage hotel? > "Heritage hotel" is more common in Asia and Europe, while "historic hotel" is more common in the U.S. overall though the terms are similar. The building and architecture of historic hotels tend to be the most important aspect. For a heritage hotel, it's mainly the cultural value along with how it influenced the community. ### Do historic hotels in Pittsfield have modern facilities? > Hotel interiors feature the modern conveniences and safety features you expect to find, while every effort is made to preserve historic facades and treasured traditions. Smart TVs, WiFi, updated bathroom facilities, and the amenities found at a contemporary hotel should be available at a historic hotel. 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