Title: 10 Best Berkshire County Luxury Resorts & Hotels for 2026 | Expedia.ca [Berkshire County Hotels](https://expedia.ca/Destinations-In-Berkshire-County.d553248635083901436.Hotel-Destinations)[Vacation Rentals in Berkshire County](https://expedia.ca/Destinations-In-Berkshire-County.d553248635083901436.Vacation-Rental-Destinations)[Berkshire County Car Rentals](https://expedia.ca/Destinations-In-Berkshire-County.d553248635083901436.Car-Rental-Destinations)[Berkshire County Vacations](https://expedia.ca/Berkshire-County.d553248635083901436.Destination-Travel-Guides) ![Williamstown which includes café scenes](https://images.trvl-media.com/place/7859/20112747-2c45-42f7-89fe-e3ed195e2395.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Luxury Hotels & Resorts in Berkshire County - ![](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 ## Top Cities in Berkshire County ![](https://mediaim.expedia.com/destination/1/5c9675f1022a9d16db477be7ba7a1dae.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Stockbridge [](https://expedia.ca/Stockbridge-Hotels-Luxury-Hotel.0-0-d162575-tLuxuryHotel.Travel-Guide-Filter-Hotels) ![Williamstown which includes café scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105596-Williamstown.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Williamstown [](https://expedia.ca/Williamstown-Hotels-Luxury-Hotel.0-0-d7859-tLuxuryHotel.Travel-Guide-Filter-Hotels) ![North Adams featuring autumn colours](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105306-The-Berkshires.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### North Adams [](https://expedia.ca/North-Adams-Hotels-Luxury-Hotel.0-0-d9137-tLuxuryHotel.Travel-Guide-Filter-Hotels) ![Lenox featuring an administrative building](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105615-Lenox.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Lenox [](https://expedia.ca/Lenox-Hotels-Luxury-Hotel.0-0-d8587-tLuxuryHotel.Travel-Guide-Filter-Hotels) ![Great Barrington](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/238000/238015-Great-Barrington.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Great Barrington [](https://expedia.ca/Great-Barrington-Hotels-Luxury-Hotel.0-0-d110336-tLuxuryHotel.Travel-Guide-Filter-Hotels) ![Pittsfield showing a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105316-The-Berkshires.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Pittsfield [](https://expedia.ca/Pittsfield-Hotels-Luxury-Hotel.0-0-d9478-tLuxuryHotel.Travel-Guide-Filter-Hotels) ![Lee featuring a sunset](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/238000/238014-Lee.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Lee [](https://expedia.ca/Lee-Hotels-Luxury-Hotel.0-0-d8572-tLuxuryHotel.Travel-Guide-Filter-Hotels) ![Hancock featuring tranquil scenes and a small town or village](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/238000/238020-Hancock-Massachusetts.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Hancock [](https://expedia.ca/Hancock-Hotels-Luxury-Hotel.0-0-d112303-tLuxuryHotel.Travel-Guide-Filter-Hotels) ## Check availability on Berkshire County Luxury Hotels Tonight [Dec 31 - Jan 1](https://www.expedia.ca/Hotel-Search?regionId=553248635083901436&startDate=2025-12-31&endDate=2026-01-01&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Jan 1 - Jan 2](https://www.expedia.ca/Hotel-Search?regionId=553248635083901436&startDate=2026-01-01&endDate=2026-01-02&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635083901436&startDate=2026-01-02&endDate=2026-01-04&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248635083901436&startDate=2026-01-09&endDate=2026-01-11&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ![](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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Berkshire-County-Luxury-Hotel.0-0-d553248635083901436-tLuxuryHotel.Hotel-Filter-Destinations)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Berkshire-County-Luxury-Hotel.0-0-d553248635083901436-tLuxuryHotel.Hotel-Filter-Destinations) ## Top Berkshire County Hotel Reviews ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "We chose this location for our family Christmas getaway because the amenities looked appealing and the price was affordable—and we were more than pleased with our three-night stay. The property is incredibly family-friendly. The pool and arcade had great hours, and while the arcade was small, it offered a fun selection of games. The pool and outdoor hot tub were kept at perfect temperatures, and even when busy, there was plenty of space for everyone. Relaxing in the hot tub during a snowstorm was one of the highlights of our trip. Each night, the common room hosted a movie night, which was wonderful to see families come together and enjoy time as a group. The front desk also offered DVD and game rentals, and it was refreshing to see families playing classic board games and laughing together—a pastime that seems rare these days. The lobby and common areas were spacious and cozy, especially with the warm fireplaces, where our family spent a few hours each evenings playing games. Our suite was roomy, comfortable, and felt like home. The well-stocked kitchen was a bonus. The staff was friendly and accommodating, and having a Stop & Shop directly across the street was incredibly convenient. We are more than pleased with this establishment and would both recommend and return for another family getaway! " [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Prospect Berkshires](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/b42c4262_y.jpg) ### Prospect Berkshires 10/10 Excellent "Wonderful stay - the property becomes a beautiful winter wonderland in December! Cabin was warm and well-designed, sauna was amazing and easily accessible all day, the staff was friendly, super responsive and drove us around the property when needed. Would recommend and plan to comeback!" [](https://expedia.ca/Great-Barrington-Hotels-Prospect-Berkshires.h116739795.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 "The rooms are outdated but still very clean, spacious and have all the necessary items for a great staying. " [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.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 "Did not have breakfast. Wish it was free but the hotel staff was amazing and the valet was great too! " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Courtyard by Marriott Lenox Berkshires](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/b4c52f47_y.jpg) ### Courtyard by Marriott Lenox Berkshires 10/10 Excellent "Clean room, friendly staff" [](https://expedia.ca/Lenox-Hotels-Courtyard-By-Marriott-Lenox-Berkshires.h18109146.Hotel-Information) ![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "Wonderful stay in a winter wonderland that evening especially with use of the heated pool and hot tub being maintained! Loved it. Shops inside were lovely as well, bars & restaurant on-site were fun with quirky decor. Whole hotel is quirky, which is fun!" [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 10/10 Excellent "The hotel is very nice and the employees are wonderful. Thank you!" [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.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 bed was very comfortable. The staff was helpful and courteous" [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c_y.jpg) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 10/10 Excellent "Perfect for a weekend away. Stagg was friendly. Room was clean and spacious. It was everything we needed and more." [](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [Aparthotels in Dalton ](https://www.expedia.ca/Dalton-Apart-Hotels.d6911-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Dalton ](https://www.expedia.ca/Dalton-Bed-And-Breakfast.d6911-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cheap Hotels in Dalton ](https://www.expedia.ca/Dalton-Hotels-Cheap-Hotels.0-0-d6911-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Dalton ](https://www.expedia.ca/Dalton-Hotels-Family-Hotel.0-0-d6911-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Dalton ](https://www.expedia.ca/Dalton-Hotels-Spa-Hotel.0-0-d6911-tSpaHotel.Travel-Guide-Filter-Hotels) - [Dalton Hotels ](https://www.expedia.ca/Dalton-Hotels.d6911.Travel-Guide-Hotels) - [Lodges in Dalton ](https://www.expedia.ca/Dalton-Lodges.d6911-aaLodges.Travel-Guide-Accommodation) - [Motels in Dalton ](https://www.expedia.ca/Dalton-Motels.d6911-aaMotels.Travel-Guide-Accommodation) - [Hotels with Early Check-in in Massachusetts ](https://www.expedia.ca/Destinations-In-Massachusetts-Hotel-With-Early-Check-In.0-0-d223-thotelwithearlycheckin.Hotel-Filter-Destinations) - [Hotels with a Lazy River in Massachusetts ](https://www.expedia.ca/Destinations-In-Massachusetts-Hotels-With-A-Lazy-River.0-0-d223-tHotelswithaLazyRiver.Hotel-Filter-Destinations) - [Hotels with Free Breakfast in Massachusetts ](https://www.expedia.ca/Destinations-In-Massachusetts-Hotels-With-Free-Breakfast.0-0-d223-tHotelswithFreeBreakfast.Hotel-Filter-Destinations) - [Mountain Hotels in Massachusetts ](https://www.expedia.ca/Destinations-In-Massachusetts-Mountain-Hotels.0-0-d223-tMountainHotels.Hotel-Filter-Destinations) - [Scuba Diving Hotels in Massachusetts ](https://www.expedia.ca/Destinations-In-Massachusetts-Scuba-Diving-Vacations.0-0-d223-tscubadivingvacations.Hotel-Filter-Destinations) - [Farmstay in Hancock ](https://www.expedia.ca/Hancock-Agritourism.d112303-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Hancock ](https://www.expedia.ca/Hancock-Apart-Hotels.d112303-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Hancock ](https://www.expedia.ca/Hancock-Bed-And-Breakfast.d112303-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Condo Rentals in Hancock ](https://www.expedia.ca/Hancock-Condos.d112303-aaCondos.Travel-Guide-Accommodation) - [Guest Houses in Hancock ](https://www.expedia.ca/Hancock-Guest-Houses.d112303-aaGuestHouses.Travel-Guide-Accommodation) - [Boutique Hotels in Hancock ](https://www.expedia.ca/Hancock-Hotels-Boutique-Hotel.0-0-d112303-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Hancock ](https://www.expedia.ca/Hancock-Hotels-Cheap-Hotels.0-0-d112303-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Hancock ](https://www.expedia.ca/Hancock-Hotels-Luxury-Hotel.0-0-d112303-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Hancock ](https://www.expedia.ca/Hancock-Hotels-Mountain-Hotels.0-0-d112303-tMountainHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Hancock ](https://www.expedia.ca/Hancock-Hotels-Pet-Friendly-Hotel.0-0-d112303-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Hancock Hotels ](https://www.expedia.ca/Hancock-Hotels.d112303.Travel-Guide-Hotels) - [Inns in Hancock ](https://www.expedia.ca/Hancock-Inns.d112303-aaInns.Travel-Guide-Accommodation) - [Resorts in Hancock ](https://www.expedia.ca/Hancock-Resort-Hotels.d112303-aaResortHotels.Travel-Guide-Accommodation) - [Hotels near Hancock Shaker Village ](https://www.expedia.ca/Hancock-Shaker-Village-Hotels.0-l6091849-0.Travel-Guide-Filter-Hotels) - [Guest Houses in Hinsdale ](https://www.expedia.ca/Hinsdale-Guest-Houses.d6005406-aaGuestHouses.Travel-Guide-Accommodation) - [Hinsdale Hotels ](https://www.expedia.ca/Hinsdale-Hotels.d6005406.Travel-Guide-Hotels) - [Hotels near Jiminy Peak Mountain Resort ](https://www.expedia.ca/Jiminy-Peak-Mountain-Resort-Hotels.0-l553248621532665536-0.Travel-Guide-Filter-Hotels) - [Guest Houses in Lanesborough ](https://www.expedia.ca/Lanesborough-Guest-Houses.d6005408-aaGuestHouses.Travel-Guide-Accommodation) - [Cheap Hotels in Lanesborough ](https://www.expedia.ca/Lanesborough-Hotels-Cheap-Hotels.0-0-d6005408-tCheapHotels.Travel-Guide-Filter-Hotels) - [Spa Hotels in Lanesborough ](https://www.expedia.ca/Lanesborough-Hotels-Spa-Hotel.0-0-d6005408-tSpaHotel.Travel-Guide-Filter-Hotels) - [Lanesborough Hotels ](https://www.expedia.ca/Lanesborough-Hotels.d6005408.Travel-Guide-Hotels) - [Inns in Lanesborough ](https://www.expedia.ca/Lanesborough-Inns.d6005408-aaInns.Travel-Guide-Accommodation) - [Vacation Homes in Lanesborough ](https://www.expedia.ca/Lanesborough-Private-Vacation-Homes.d6005408-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Aparthotels in Lenox ](https://www.expedia.ca/Lenox-Apart-Hotels.d8587-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Lenox ](https://www.expedia.ca/Lenox-Bed-And-Breakfast.d8587-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Castles in Lenox ](https://www.expedia.ca/Lenox-Castles.d8587-aaCastles.Travel-Guide-Accommodation) - [Chalets in Lenox ](https://www.expedia.ca/Lenox-Chalets.d8587-aaChalets.Travel-Guide-Accommodation) - [Guest Houses in Lenox ](https://www.expedia.ca/Lenox-Guest-Houses.d8587-aaGuestHouses.Travel-Guide-Accommodation) - [Holiday Park Resorts in Lenox ](https://www.expedia.ca/Lenox-Holiday-Parks.d8587-aaHolidayParks.Travel-Guide-Accommodation) - [Adults Only Resorts & in Lenox ](https://www.expedia.ca/Lenox-Hotels-Adults-Only-Resorts.0-0-d8587-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Lenox ](https://www.expedia.ca/Lenox-Hotels-Beach-Hotel.0-0-d8587-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Lenox ](https://www.expedia.ca/Lenox-Hotels-Boutique-Hotel.0-0-d8587-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Lenox ](https://www.expedia.ca/Lenox-Hotels-Cheap-Hotels.0-0-d8587-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Lenox ](https://www.expedia.ca/Lenox-Hotels-Family-Hotel.0-0-d8587-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Historic Hotels in Lenox ](https://www.expedia.ca/Lenox-Hotels-Historic-Hotel.0-0-d8587-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in Lenox ](https://www.expedia.ca/Lenox-Hotels-Honeymoon-Hotels.0-0-d8587-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in Lenox ](https://www.expedia.ca/Lenox-Hotels-Hotels-With-Indoor-Pool.0-0-d8587-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in Lenox ](https://www.expedia.ca/Lenox-Hotels-LGBT-Friendly-Hotel.0-0-d8587-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Lenox ](https://www.expedia.ca/Lenox-Hotels-Luxury-Hotel.0-0-d8587-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Lenox ](https://www.expedia.ca/Lenox-Hotels-Romantic-Hotel.0-0-d8587-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Lenox ](https://www.expedia.ca/Lenox-Hotels-Spa-Hotel.0-0-d8587-tSpaHotel.Travel-Guide-Filter-Hotels) - [Lenox Hotels ](https://www.expedia.ca/Lenox-Hotels.d8587.Travel-Guide-Hotels) - [Inns in Lenox ](https://www.expedia.ca/Lenox-Inns.d8587-aaInns.Travel-Guide-Accommodation) - [Resorts in Lenox ](https://www.expedia.ca/Lenox-Resort-Hotels.d8587-aaResortHotels.Travel-Guide-Accommodation) - [B&B in Pittsfield ](https://www.expedia.ca/Pittsfield-Bed-And-Breakfast.d9478-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Pittsfield ](https://www.expedia.ca/Pittsfield-Chalets.d9478-aaChalets.Travel-Guide-Accommodation) - [Guest Houses in Pittsfield ](https://www.expedia.ca/Pittsfield-Guest-Houses.d9478-aaGuestHouses.Travel-Guide-Accommodation) - [Holiday Park Resorts in Pittsfield ](https://www.expedia.ca/Pittsfield-Holiday-Parks.d9478-aaHolidayParks.Travel-Guide-Accommodation) - [Hostels in Pittsfield ](https://www.expedia.ca/Pittsfield-Hostels.d9478-aaHostels.Travel-Guide-Accommodation) - [Boutique Hotels in Pittsfield ](https://www.expedia.ca/Pittsfield-Hotels-Boutique-Hotel.0-0-d9478-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Pittsfield ](https://www.expedia.ca/Pittsfield-Hotels-Cheap-Hotels.0-0-d9478-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Pittsfield ](https://www.expedia.ca/Pittsfield-Hotels-Hotel-With-Pool.0-0-d9478-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with smoking rooms in Pittsfield ](https://www.expedia.ca/Pittsfield-Hotels-Hotels-With-Smoking-Rooms.0-0-d9478-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in Pittsfield ](https://www.expedia.ca/Pittsfield-Hotels-LGBT-Friendly-Hotel.0-0-d9478-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Pittsfield ](https://www.expedia.ca/Pittsfield-Hotels-Luxury-Hotel.0-0-d9478-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Pittsfield ](https://www.expedia.ca/Pittsfield-Hotels-Pet-Friendly-Hotel.0-0-d9478-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Ski Hotels in Pittsfield ](https://www.expedia.ca/Pittsfield-Hotels-Ski-Hotel.0-0-d9478-tSkiHotel.Travel-Guide-Filter-Hotels) - [Pittsfield Hotels ](https://www.expedia.ca/Pittsfield-Hotels.d9478.Travel-Guide-Hotels) - [Motels in Pittsfield ](https://www.expedia.ca/Pittsfield-Motels.d9478-aaMotels.Travel-Guide-Accommodation) - [Resorts in Pittsfield ](https://www.expedia.ca/Pittsfield-Resort-Hotels.d9478-aaResortHotels.Travel-Guide-Accommodation) - [Hotels near Pittsfield Station ](https://www.expedia.ca/Pittsfield-Station-Hotels.d6195403.Travel-Guide-Hotels) - [Motels in Pittsfield Station ](https://www.expedia.ca/Pittsfield-Station-Motels.d6195403-aaMotels.Travel-Guide-Accommodation) - [Hotels near Tanglewood Music Center ](https://www.expedia.ca/Tanglewood-Music-Center-Hotels.0-l503292-0.Travel-Guide-Filter-Hotels) - [Hotels near Ventfort Hall Mansion and Gilded Age Museum ](https://www.expedia.ca/Ventfort-Hall-Mansion-And-Gilded-Age-Museum-Hotels.0-l553248621532665270-0.Travel-Guide-Filter-Hotels) - [Flights to Lenox ](https://www.expedia.ca/Cheap-Flights-To-Lenox.d8587.Travel-Guide-Flights) - [Flights to Pittsfield ](https://www.expedia.ca/Cheap-Flights-To-Pittsfield.d9478.Travel-Guide-Flights) - [Flights from Lenox ](https://www.expedia.ca/lp/flights/8587/flights-from-lenox) - [Flights from Bangor (BGR) to Pittsfield (PSF) ](https://www.expedia.ca/lp/flights/bgr/psf/bangor-to-pittsfield) - [Flights from Boston (BOS) to Pittsfield (PSF) ](https://www.expedia.ca/lp/flights/bos/psf/boston-to-pittsfield) - [Flights from Ithaca (ITH) to Pittsfield (PSF) ](https://www.expedia.ca/lp/flights/ith/psf/ithaca-to-pittsfield) - [Flights from Plattsburgh (PBG) to Pittsfield (PSF) ](https://www.expedia.ca/lp/flights/pbg/psf/plattsburgh-to-pittsfield) - [Flights from Phoenix (PHX) to Pittsfield (PSF) ](https://www.expedia.ca/lp/flights/phx/psf/phoenix-to-pittsfield) - [Flights from Richmond (RIC) to Pittsfield (PSF) ](https://www.expedia.ca/lp/flights/ric/psf/richmond-to-pittsfield) - [Flights from Seattle (SEA) to Pittsfield (PSF) ](https://www.expedia.ca/lp/flights/sea/psf/seattle-to-pittsfield) - [Flights from Toronto (YYZ) to Pittsfield (PSF) ](https://www.expedia.ca/lp/flights/yyz/psf/toronto-to-pittsfield) - [Canoe Meadows Wildlife Sanctuary ](https://www.expedia.ca/Canoe-Meadows-Wildlife-Sanctuary-Pittsfield.d553248621532665285.Vacation-Attraction) - [Hancock Shaker Village ](https://www.expedia.ca/Hancock-Shaker-Village-Pittsfield.d6091849.Vacation-Attraction) - [Lenox Library ](https://www.expedia.ca/Lenox-Library-Lenox.d553248621532665268.Vacation-Attraction) - [Ventfort Hall Mansion and Gilded Age Museum ](https://www.expedia.ca/Ventfort-Hall-Mansion-And-Gilded-Age-Museum-Lenox.d553248621532665270.Vacation-Attraction) - [Avis Rental Cars in Lenox ](https://www.expedia.ca/Avis-Car-Rentals-In-Lenox.d8587-c41.Car-Rental-Guide-Suppliers) - [Budget Rental Cars in Pittsfield ](https://www.expedia.ca/Budget-Car-Rentals-In-Pittsfield.d9478-c39.Car-Rental-Guide-Suppliers) - [Car rental Hancock ](https://www.expedia.ca/Car-Rentals-In-Hancock.d112303.Car-Rental-Guide) - [Car rentals near Jiminy Peak Mountain Resort ](https://www.expedia.ca/Car-Rentals-In-Jiminy-Peak-Mountain-Resort.d553248621532665536.Car-Rental-Guide) - [Car rental Lenox ](https://www.expedia.ca/Car-Rentals-In-Lenox.d8587.Car-Rental-Guide) - [Rental cars Pittsfield Municipal airport ](https://www.expedia.ca/Car-Rentals-In-Pittsfield-Municipal.d6031274.Car-Rental-Guide) - [Car rental Pittsfield ](https://www.expedia.ca/Car-Rentals-In-Pittsfield.d9478.Car-Rental-Guide) - [Book Luxury Hotels in Berkshire County on Expedia.com ](https://www.expedia.com/Destinations-In-Berkshire-County-Luxury-Hotel.0-0-d553248635083901436-tLuxuryHotel.Hotel-Filter-Destinations)