Title: Book the Best HISTORIC Hotels in Stockbridge in 2025 | Expedia.ca [Stockbridge Travel Guide](https://expedia.ca/Stockbridge.dx162575)[Hotels in Stockbridge](https://expedia.ca/Stockbridge-Hotels.d162575.Travel-Guide-Hotels)[Vacation Rentals in Stockbridge](https://expedia.ca/Stockbridge-Vacation-Rentals.d162575.Travel-Guide-VacationRentals)[Flights to Stockbridge](https://expedia.ca/Cheap-Flights-To-Stockbridge.d162575.Travel-Guide-Flights)[Stockbridge Car Rentals](https://expedia.ca/Car-Rentals-In-Stockbridge.d162575.Car-Rental-Guide)[Stockbridge Vacation Packages](https://expedia.ca/Stockbridge.d162575.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/5c9675f1022a9d16db477be7ba7a1dae.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Stockbridge, MA from CA $273 ![](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 Stockbridge Historic Hotels Tonight [Oct 20 - Oct 21](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2025-10-20&endDate=2025-10-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 21 - Oct 22](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2025-10-21&endDate=2025-10-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Stockbridge 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) ![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) ![Front of property - evening/night](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/4d2e9eec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Red Lion Inn Stockbridge 8.8/10 Excellent (1014) "Picture perfect Inn" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jeff CA $188 CA $273 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/9abb62fb_edited_7b4b.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 $327 total includes taxes & fees Oct 21 - Oct 22 [](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=2025-11-03&endDate=2025-11-04®ionId=162575&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Stockbridge Hotel Reviews ![The Red Lion Inn](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "In a very nice annex suite." [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![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 "Enjoyable stay. Staff were very nice. " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](//images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "Great stay-- would stay here again-- safe, nice welcome from Cameron at front desk, room was clean and cozy. Bed was very comfortable. Didn't have breakfast. I usually stay in Pittsfield at a hotel that has given me a discount since March when my mother was put into a nursing home. I normally try to come down twice a month from CNY--needless to say it is expensive for me.. Random question-- do you offer discounts?" [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.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 "Clean room, nice view" [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.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 "Breakfast was great" [](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood](//images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/587b0e23_y.jpg) ### The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood 10/10 Excellent "My husband and I thoroughly enjoyed our stay at the Stockbridge Inn. Diane, the owner, greeted us warmly and escorted us to our room. Our accommodations were comfortable, warm and spacious and quiet enough for us to have a good night sleep. Diane was very helpful in recommending other accommodations for a large family function that she as unable to help us with. The breakfasts were incredible and the staff was there to answer our any desire. On a scale of 1-10 I would rate this Inn a ten." [](https://expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](//images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 10/10 Excellent "Great place to have a girls night for old friends when one of us is back in town for a night. Very convenient place well kept. " [](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Howard Johnson by Wyndham Lenox](//images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84_y.jpg) ### Howard Johnson by Wyndham Lenox 10/10 Excellent "Good for the one night drive through! " [](https://expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) ![Hampton Inn & Suites Berkshires-Lenox](//images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg) ### Hampton Inn & Suites Berkshires-Lenox 10/10 Excellent "Felt comfortable and safe. Nice pool and gym facility." [](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ## Frequently asked questions ### What should a history enthusiast expect from a trip to Stockbridge? > A trip to the historical places in Stockbridge is probably first on your travel itinerary. Why not absorb the local color with a visit to the bars? ### What's the best place to stay in Stockbridge that's close to historical sites? > Based on our travel expertise, [The Red Lion Inn](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) is a top historic hotel bookable on our site and it features free WiFi. Naumkeag Museum is a short 12-minute walk away. ### How many historically relevant hotels are there in Stockbridge? > Stockbridge is home to 51 hotels and other lodging options bookable on Expedia though you won't find many designated historic hotels. ### What are the top historical places and other sights to visit in Stockbridge? > Stockbridge is notable for landmarks like Naumkeag Museum, Frelinghuysen Morris House and Studio, and Mission House. Cultural venues include Norman Rockwell Museum, Schantz Galleries, and Berkshire Theatre Festival. A couple of additional sights to add to your agenda are National Shrine of the Divine Mercy and Berkshire Botanical Garden. ### What is a historic hotel like in Stockbridge? > Guests who book a historic hotel can enjoy a vacation in a building that has an officially recognized national historic designation. A stately home, palace or even a lodge, old police station, or skyscraper can be transformed into a historic hotel as long as it's a place of special interest. Traditional architecture and period features are typically found in the communal spaces and guestrooms of such hotels in Stockbridge, giving a sense of history. ### What is the difference between a historic hotel and a heritage hotel? > "Heritage hotel" is a term often used in Asia and Europe, while "historic hotel" is more common in the U.S. but overall the terms are quite similar. The architecture and building of a historic hotel tends to be what's most important. For a heritage hotel, it's often the cultural value and how it inspired the community. ### Do historic hotels in Stockbridge have modern facilities? > Yes, every effort is made to preserve treasured traditions and historic facades, but interiors include modern conveniences and safety features. Visitors should expect the popular amenities you'd find in a hotel such as private rooms with updated bathroom facilities, WiFi, and more. 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