Title: Book the Best Pittsfield FAMILY FRIENDLY Hotels from CA $105 - Kid-Friendly Hotels in Pittsfield, MA | 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 Family Hotels in Pittsfield, MA from CA $105 ![](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 Family Hotels Tonight [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&travelerType=family_friendly) Tomorrow [Oct 31 - Nov 1](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-10-31&endDate=2025-11-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) 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&travelerType=family_friendly) 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&travelerType=family_friendly) ## Top Pittsfield Family Hotels ![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/1000000/790000/790000/789964/90dd9d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/0e628046.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) ### Best Western Plus Berkshire Hills Inn & Suites Pittsfield 8.6/10 Excellent (1022) "I have stayed here many times and it is consistently a comfortable, clean and quiet place." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeanine CA $130 CA $146 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.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/1000000/120000/119300/119210/2b026b4b.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 (55) "Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marti CA $177 CA $197 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.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) ![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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/6b95ddf5.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 (933) "Friendly staff and clean rooms. Loved the onsite restaurant & bar." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carmen 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, 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) ![Exterior](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/3fc8dc3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/adca2c72.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 7.8/10 Good (6) "Very clean and spacious! We enjoyed our stay with our small pup!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ann C. CA $375 CA $686 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-Home-W-Lake-And-Mountain-Views-Near-Skiing.h106650307.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/c189cee9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/5d0aa061.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/ed3ffaa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/34fa691f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hancock Village Inn Near Jiminy Peak Hancock 10/10 Exceptional (15) "Amazing Inn. Cozy and everything we needed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Price F. CA $835 CA $1,549 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Pittsfield-Hotels-Hancock-Village-Inn-At-Jiminy-Peak.h89806253.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) ![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/bd64a090.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 (801) "Good service and people" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jerod CA $94 CA $105 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Pittsfield-Hotels-Econo-Lodge.h1543.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/c0933de7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker, dining tables](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/5fd0e723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/754813dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/b38994ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Element Lenox Berkshires Lenox 9.6/10 Exceptional (9) "New hotel very nice" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) joel CA $188 CA $210 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) ![In-room safe, desk, free cribs/infant beds, free rollaway beds](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/7c78ca51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/7f86e411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms, Non Smoking](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/723a5f12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Non Smoking](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/a393dfb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelodge by Wyndham Great Barrington Berkshires Great Barrington 7.6/10 Good (556) "The staff were very friendly and accommodating " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tom CA $105 CA $117 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1060000/1052400/1052319/ea181a79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1060000/1052400/1052319/0bce9997.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1060000/1052400/1052319/a2bec263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1060000/1052400/1052319/fa243b02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites East Greenbush - Albany Castleton-on-Hudson 8.4/10 Very good (1001) "Nice place for some rest, breakfast was very good, variety and great selection " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $147 CA $163 total includes taxes & fees Nov 14 - Nov 15 [](https://www.expedia.ca/Albany-Hotels-Comfort-Inn-Suites-East-Greenbush-Albany.h1052319.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Non Lakeside Superior Room, 2 Queen beds](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/d3eea453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ba9d3ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/53f3f179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel Lee 9.0/10 Wonderful (1002) "Great Indian restaurant in the hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris CA $148 CA $166 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.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=2025-11-13&endDate=2025-11-14®ionId=9478&adults=2&travelerType=family_friendly&sort=RECOMMENDED&openPlayBack=true) ## Top Pittsfield 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 "The Red Lion Hotel was a great place to stay!! I would definitley come back again and stay there! I loved the bar downstairs and the restaurant! Our room was perfect and we had lots of room! The bed was super comfy - a marshmallow bed!! LOL! The location was nice to walk to the different shops in town! Fun place! " [](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 "Good location; reasonable price; very clean and quiet - would definitely return" [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.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 "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) ## Frequently asked questions ### What's Pittsfield like for family-friendly vacations? > The historic destination of Pittsfield is a good choice if you've been thinking about a trip with your kids. The biking trails, entertainment, and lake views are just some of the things that make this a good place for family vacations. Take to the air and fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is the closest airport, or Hudson, NY (HCC-Columbia County), which is located 25.7 mi (41.4 km) from the city center. ### What's the best hotel when traveling with kids to Pittsfield? > [Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) is a hotel with an indoor pool and a restaurant, and it's a top choice on Expedia for families. Other choices for your family trip include [Holiday Inn Express & Suites Pittsfield - Berkshires by IHG](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) and [Best Western Plus Berkshire Hills Inn & Suites](https://www.expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information). ### When's the best time to book a family-friendly vacation in Pittsfield? > The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Pittsfield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall. ### What's there to see and do with your family in Pittsfield? > Colonial Theater, Barrington Stage Company, and Bousquet Ski Area are interesting attractions you and your family will enjoy exploring while you are staying in Pittsfield. Make sure you have lots of time for activities like Berkshire Athenaeum and Crane Museum of Papermaking. ### What's the best way for us to get around Pittsfield? > To see more of the surrounding area, ride one of the trains from Pittsfield Intermodal Transportation Center or Pittsfield Station. Pittsfield might not have many public transit options so consider renting a car to explore more. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [B&B in Berkshire County](https://www.expedia.ca/Berkshire-County-Bed-And-Breakfast.d553248635083901436-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Berkshire County](https://www.expedia.ca/Berkshire-County-Chalets.d553248635083901436-aaChalets.Travel-Guide-Accommodation) - [Inns in Berkshire County](https://www.expedia.ca/Berkshire-County-Inns.d553248635083901436-aaInns.Travel-Guide-Accommodation) - [Resorts in Berkshire County](https://www.expedia.ca/Berkshire-County-Resort-Hotels.d553248635083901436-aaResortHotels.Travel-Guide-Accommodation) - [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) - [Beach Hotel Hotels in Berkshire County](https://www.expedia.ca/Destinations-In-Berkshire-County-Beach-Hotel.0-0-d553248635083901436-tBeachHotel.Hotel-Filter-Destinations) - [Hotels with a Pool in Berkshire County](https://www.expedia.ca/Destinations-In-Berkshire-County-Hotel-With-Pool.0-0-d553248635083901436-tHotelwithPool.Hotel-Filter-Destinations) - [Luxury Hotels in Berkshire County](https://www.expedia.ca/Destinations-In-Berkshire-County-Luxury-Hotel.0-0-d553248635083901436-tLuxuryHotel.Hotel-Filter-Destinations) - [Pet-Friendly Hotels in Berkshire County](https://www.expedia.ca/Destinations-In-Berkshire-County-Pet-Friendly-Hotel.0-0-d553248635083901436-tPetfriendlyHotel.Hotel-Filter-Destinations) - [Ski Hotels in Berkshire County](https://www.expedia.ca/Destinations-In-Berkshire-County-Ski-Hotel.0-0-d553248635083901436-tSkiHotel.Hotel-Filter-Destinations) - [Berkshire County Hotels](https://www.expedia.ca/Destinations-In-Berkshire-County.d553248635083901436.Hotel-Destinations) - [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) - [Historic Hotels in Hancock](https://www.expedia.ca/Hancock-Hotels-Historic-Hotel.0-0-d112303-tHistoricHotel.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) - [Spa Hotels in Hancock](https://www.expedia.ca/Hancock-Hotels-Spa-Hotel.0-0-d112303-tSpaHotel.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) - [Luxury Hotels in Hinsdale](https://www.expedia.ca/Hinsdale-Hotels-Luxury-Hotel.0-0-d6005406-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Hinsdale](https://www.expedia.ca/Hinsdale-Hotels-Spa-Hotel.0-0-d6005406-tSpaHotel.Travel-Guide-Filter-Hotels) - [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) - [Hotels near Mount Greylock State Reservation Visitor Center](https://www.expedia.ca/Mount-Greylock-State-Reservation-Visitor-Center-Hotels.0-l6272782-0.Travel-Guide-Filter-Hotels) - [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) - [Aparthotels in Richmond](https://www.expedia.ca/Richmond-Apart-Hotels.d151138-aaApartHotels.Travel-Guide-Accommodation) - [Chalets in Richmond](https://www.expedia.ca/Richmond-Chalets.d151138-aaChalets.Travel-Guide-Accommodation) - [Holiday Park Resorts in Richmond](https://www.expedia.ca/Richmond-Holiday-Parks.d151138-aaHolidayParks.Travel-Guide-Accommodation) - [Richmond Hotels](https://www.expedia.ca/Richmond-Hotels.d151138.Travel-Guide-Hotels) - [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 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) - [Richmond Vacations](https://www.expedia.ca/Richmond.d151138.Destination-Travel-Guides) - [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) - [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) - [Dalton Vacation Rentals](https://www.expedia.ca/Dalton-Vacation-Rentals.d6911.Travel-Guide-VacationRentals) - [Book Family Hotels in Pittsfield on Expedia.com](https://www.expedia.com/Pittsfield-Hotels-Family-Hotel.0-0-d9478-tFamilyHotel.Travel-Guide-Filter-Hotels)