Title: TOP Family-Friendly Hotels in The Berkshires, MA for 2026 - The Berkshires Family Welcoming Hotels | Expedia.co.uk [The Berkshires Travel Guide](https://expedia.co.uk/The-Berkshires.dx6047665)[Hotels in The Berkshires](https://expedia.co.uk/The-Berkshires-Hotels.d6047665.Travel-Guide-Hotels)[Holiday Rentals in The Berkshires](https://expedia.co.uk/The-Berkshires-Holiday-Rentals.d6047665.Travel-Guide-HolidayRentals)[Flights to The Berkshires](https://expedia.co.uk/Cheap-Flights-To-The-Berkshires.d6047665.Travel-Guide-Flights)[The Berkshires Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-The-Berkshires.d6047665.Car-Hire-Guide)[The Berkshires Holidays](https://expedia.co.uk/The-Berkshires.d6047665.Holidays-City-Breaks) ![The Berkshires featuring flowers](https://images.trvl-media.com/place/6047665/e95ad08c-cd3f-48ea-b01c-31171bbd50b7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Photo courtesy of Berkshire Visitors Bureau # Find Family-Friendly Hotels in The Berkshires, MA - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on The Berkshires Family-Friendly Hotels Tonight [8 Jan - 9 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2026-01-08&endDate=2026-01-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Tomorrow [9 Jan - 10 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2026-01-09&endDate=2026-01-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) This weekend [9 Jan - 11 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Next weekend [16 Jan - 18 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2026-01-16&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) ## Our top choices for The Berkshires family-friendly hotels ![Arcade](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/5389bc61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/4f7ca94f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/0fe63f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Villa, 3 Bedrooms | In-room safe, iron/ironing board, free cots/infant beds, WiFi](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/5aedd4f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG [](https://www.expedia.co.uk/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) South Lee 9.0/10 Wonderful (818) "We had a great stay! Karaoke in the bar was a blast!! Great little condo!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephanie £92 includes taxes & fees 14 Jan - 15 Jan [](https://www.expedia.co.uk/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![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) ![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) ![Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/0e628046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Berkshire Hills Inn & Suites [](https://www.expedia.co.uk/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) Pittsfield 8.6/10 Excellent (1002) "Very friendly and good Breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jesse £63 includes taxes & fees 27 Jan - 28 Jan [](https://www.expedia.co.uk/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/f2aaf746.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/1d50a551.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/32c535e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/15c993a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires [](https://www.expedia.co.uk/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information) Great Barrington 9.4/10 Exceptional (761) "Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dinh £112 includes taxes & fees 25 Jan - 26 Jan [](https://www.expedia.co.uk/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.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 curtains](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/207845f4.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) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG [](https://www.expedia.co.uk/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) Pittsfield 8.0/10 Very good (1001) "Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa £81 includes taxes & fees 23 Jan - 24 Jan [](https://www.expedia.co.uk/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.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 | Premium bedding, desk, laptop workspace, blackout curtains](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) ![BBQ/picnic Area](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/4fd790fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel [](https://www.expedia.co.uk/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) Lee 9.0/10 Wonderful (1002) "Room was clean and the staff was super friendly and helpful!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ethan £81 includes taxes & fees 2 Feb - 3 Feb [](https://www.expedia.co.uk/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.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) ![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) ![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) ### Element Lenox Berkshires [](https://www.expedia.co.uk/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) Lenox 9.6/10 Exceptional (15) "The room we stayed in was extremely clean and comfy. The whole hotel was very nice and had an awesome breakfast. Will be staying here again for sure. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Keith £115 includes taxes & fees 20 Jan - 21 Jan [](https://www.expedia.co.uk/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) ![Superior Cabin, 1 King Bed, Roll-in Shower, Garden View | Egyptian cotton sheets, premium bedding, down duvets, minibar](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/c9a28f6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, pool loungers](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/a2e409f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Cabin, 1 King Bed, Lake View | Egyptian cotton sheets, premium bedding, down duvets, minibar](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/7209b504.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room, 1 King Bed, Garden View | Egyptian cotton sheets, premium bedding, down duvets, minibar](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/f581b284.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Prospect Berkshires [](https://www.expedia.co.uk/Great-Barrington-Hotels-Prospect-Berkshires.h116739795.Hotel-Information) Egremont 9.6/10 Exceptional (18) "Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura £201 includes taxes & fees 13 Jan - 14 Jan [](https://www.expedia.co.uk/Great-Barrington-Hotels-Prospect-Berkshires.h116739795.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/2b026b4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, iron/ironing board, free cots/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 [](https://www.expedia.co.uk/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) Pittsfield 9.4/10 Exceptional (73) "Very clean and friendly staff that go above and beyond for their guests even in a snow storm! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kira £102 includes taxes & fees 25 Jan - 26 Jan [](https://www.expedia.co.uk/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) ![Skiing](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/107313fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/ddfadf2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/662f1ebe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 Bedroom Condo 1/2 mile from base | In-room dining](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/40940c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jiminy Peak Mountain Resort [](https://www.expedia.co.uk/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information) Hancock 8.2/10 Very good (988) "nice and clean, good customer service, but the room is smell. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Huang £181 includes taxes & fees 11 Jan - 12 Jan [](https://www.expedia.co.uk/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information) ![Children’s play area – outdoor](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/6c30ed5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/52ce390c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/9d6fa2c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/c64cd286.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maple Terrace Motel [](https://www.expedia.co.uk/Williamstown-Hotels-Maple-Terrace-Motel.h13278987.Hotel-Information) Williamstown 9.6/10 Exceptional (595) "Cute place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa £82 includes taxes & fees 11 Jan - 12 Jan [](https://www.expedia.co.uk/Williamstown-Hotels-Maple-Terrace-Motel.h13278987.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.co.uk/Hotel-Search?startDate=2026-01-22&endDate=2026-01-23®ionId=6047665&adults=2&travelerType=family_friendly&sort=RECOMMENDED&openPlayBack=true) ## Find out more about The Berkshires ### Family friendly things to do in The Berkshires The Berkshires is a paradise of family-friendly activities that promise adventure and education for all ages. Start your journey at the Berkshire Museum in Pittsfield, where children can marvel at interactive exhibits, admire local art, and even meet live animals. For outdoor enthusiasts, the Bousquet Mountain offers skiing in winter and mountain biking in summer, ensuring thrill-seekers of all ages are entertained. Don’t miss the picturesque hiking trails at Mount Greylock State Reservation, which boasts stunning views and picnic spots perfect for family lunches. Arts lovers will appreciate the Tanglewood Music Center, where families can enjoy concerts in a stunning natural setting—some performances are even designed for children. Finally, the Norman Rockwell Museum in Stockbridge invites families to explore the life and works of one of America’s beloved illustrators, with activities tailored for young visitors. When it comes to accommodation, the area surrounding Lenox and Stockbridge features a range of family-friendly hotels that cater to your every need. Many establishments offer spacious suites, on-site dining, and activities like swimming pools and game rooms, ensuring that relaxation and fun go hand in hand. Staying here places you in close nearby top attractions, making it easy to explore without the hassle of long drives. The attentive service and comfortable amenities found in these hotels will make your family feel pampered, allowing for a seamless and enjoyable getaway in the beautiful Berkshires. ## Top The Berkshires Hotel Reviews ![Hampton Inn & Suites Berkshires-Lenox](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg) ### Hampton Inn & Suites Berkshires-Lenox 10/10 Excellent "Very clean, modern hotel. Would definitely stay here again. " [](https://expedia.co.uk/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.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 "Absolutely fabulous!" [](https://expedia.co.uk/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "Great staff, room was huge and comfortable. " [](https://expedia.co.uk/Pittsfield-Hotels-Hotel-On-North.h10246103.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 "All of the above!" [](https://expedia.co.uk/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![The Porches Inn at Mass MoCA](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/dcf42e0d_y.jpg) ### The Porches Inn at Mass MoCA 10/10 Excellent "Wow. This hotel is such a great find. Not only is it clean and unique, the rooms are large and the staff are super helpful and nice. Breakfast was nice. The pool was slightly colder than I expected but it was 5 degrees outside and windy so its understandable. The hot tub was very comfortable. I would love to stay here again. My kids said this is their favorite hotel we have ever stayed at which is high praise since we travel frequently and have stayed in a ton of hotels!" [](https://expedia.co.uk/North-Adams-Hotels-The-Porches-Inn.h7662392.Hotel-Information) ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 10/10 Excellent "Nice warm pool and hot tub. Good little fitness center. " [](https://expedia.co.uk/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg) ### Hotel Downstreet, an Ascend Collection Hotel 10/10 Excellent "friendly accommodating staff" [](https://expedia.co.uk/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.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.co.uk/Lenox-Hotels-Courtyard-By-Marriott-Lenox-Berkshires.h18109146.Hotel-Information) ![Best Western Plus Berkshire Hills Inn & Suites](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg) ### Best Western Plus Berkshire Hills Inn & Suites 10/10 Excellent "Loved having coffee and tea 24/7" [](https://expedia.co.uk/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - More ways to book - [3 Star Hotels in Great Barrington ](https://www.expedia.co.uk/3Star-Great-Barrington-Hotels.s30-0-d110336.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Chester ](https://www.expedia.co.uk/4Star-Chester-Hotels.s40-0-d6005399.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Great Barrington ](https://www.expedia.co.uk/4Star-Great-Barrington-Hotels.s40-0-d110336.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Great Barrington ](https://www.expedia.co.uk/5Star-Great-Barrington-Hotels.s50-0-d110336.Travel-Guide-Filter-Hotels) - [Hotels near Animagic Museum of Animation ](https://www.expedia.co.uk/Animagic-Museum-Of-Animation-Hotels.0-l553248621560926701-0.Travel-Guide-Filter-Hotels) - [Becket Hotels ](https://www.expedia.co.uk/Becket-Hotels.d6005395.Travel-Guide-Hotels) - [Blandford Hotels ](https://www.expedia.co.uk/Blandford-Hotels.d80625.Travel-Guide-Hotels) - [Chester Hotels ](https://www.expedia.co.uk/Chester-Hotels.d6005399.Travel-Guide-Hotels) - [Hotels with a Bar in Massachusetts ](https://www.expedia.co.uk/Destinations-In-Massachusetts-Hotel-With-A-Bar.0-0-d223-thotelwithabar.Hotel-Filter-Destinations) - [Hotels with Connecting Rooms in Massachusetts ](https://www.expedia.co.uk/Destinations-In-Massachusetts-Hotel-With-Connecting-Rooms.0-0-d223-thotelwithconnectingrooms.Hotel-Filter-Destinations) - [Hotels with Early Check-in in Massachusetts ](https://www.expedia.co.uk/Destinations-In-Massachusetts-Hotel-With-Early-Check-In.0-0-d223-thotelwithearlycheckin.Hotel-Filter-Destinations) - [Hotels with Gym in Massachusetts ](https://www.expedia.co.uk/Destinations-In-Massachusetts-Hotel-With-Gym.0-0-d223-thotelwithgym.Hotel-Filter-Destinations) - [Hotels with Laundry Service in Massachusetts ](https://www.expedia.co.uk/Destinations-In-Massachusetts-Hotel-With-Laundry-Service.0-0-d223-thotelwithlaundryservice.Hotel-Filter-Destinations) - [Hotels with Room Service in Massachusetts ](https://www.expedia.co.uk/Destinations-In-Massachusetts-Hotel-With-Room-Service.0-0-d223-thotelwithroomservice.Hotel-Filter-Destinations) - [Cabin Rentals in Great Barrington ](https://www.expedia.co.uk/Great-Barrington-Cabins.d110336-aaCabins.Travel-Guide-Accommodation) - [Chalets in Great Barrington ](https://www.expedia.co.uk/Great-Barrington-Chalets.d110336-aaChalets.Travel-Guide-Accommodation) - [Beach Resorts & in Great Barrington ](https://www.expedia.co.uk/Great-Barrington-Hotels-Beach-Hotels.0-0-d110336-tBeachHotels.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Great Barrington ](https://www.expedia.co.uk/Great-Barrington-Hotels-Budget-Hotels.0-0-d110336-tBudgetHotels.Travel-Guide-Filter-Hotels) - [Business Hotels in Great Barrington ](https://www.expedia.co.uk/Great-Barrington-Hotels-Business-Hotel.0-0-d110336-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Casino Hotels in Great Barrington ](https://www.expedia.co.uk/Great-Barrington-Hotels-Casino-Hotel.0-0-d110336-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Golf Hotels in Great Barrington ](https://www.expedia.co.uk/Great-Barrington-Hotels-Golf-Hotels.0-0-d110336-tGolfHotels.Travel-Guide-Filter-Hotels) - [Hilton Hotels in Great Barrington ](https://www.expedia.co.uk/Great-Barrington-Hotels-Hilton-Hotels.0-0-d110336--bHiltonHotels.Travel-Guide-Filter-Hotels) - [Hotels with Gym in Great Barrington ](https://www.expedia.co.uk/Great-Barrington-Hotels-Hotel-With-Gym.0-0-d110336-thotelwithgym.Travel-Guide-Filter-Hotels) - [Hotels with Laundry Service in Great Barrington ](https://www.expedia.co.uk/Great-Barrington-Hotels-Hotel-With-Laundry-Service.0-0-d110336-thotelwithlaundryservice.Travel-Guide-Filter-Hotels) - [Hotels with Restaurant in Great Barrington ](https://www.expedia.co.uk/Great-Barrington-Hotels-Hotel-With-Restaurant.0-0-d110336-thotelwithrestaurant.Travel-Guide-Filter-Hotels) - [Hotels with Indoor Pools in Great Barrington ](https://www.expedia.co.uk/Great-Barrington-Hotels-Hotels-With-Indoor-Pools.0-0-d110336-tHotelswithIndoorPools.Travel-Guide-Filter-Hotels) - [Hotels with Pool in Great Barrington ](https://www.expedia.co.uk/Great-Barrington-Hotels-Hotels-With-Pool.0-0-d110336-tHotelswithPool.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Great Barrington ](https://www.expedia.co.uk/Great-Barrington-Hotels-Luxury-Hotel.0-0-d110336-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Great Barrington ](https://www.expedia.co.uk/Great-Barrington-Hotels-Mountain-Hotel.0-0-d110336-tmountainhotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Great Barrington ](https://www.expedia.co.uk/Great-Barrington-Hotels-Pet-Friendly-Hotel.0-0-d110336-tPetFriendlyHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Great Barrington ](https://www.expedia.co.uk/Great-Barrington-Hotels-Romantic-Hotel.0-0-d110336-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Ski Hotels in Great Barrington ](https://www.expedia.co.uk/Great-Barrington-Hotels-Ski-Hotels.0-0-d110336-tSkiHotels.Travel-Guide-Filter-Hotels) - [Spa Hotels in Great Barrington ](https://www.expedia.co.uk/Great-Barrington-Hotels-Spa-Hotels.0-0-d110336-tSpaHotels.Travel-Guide-Filter-Hotels) - [Wedding Hotels in Great Barrington ](https://www.expedia.co.uk/Great-Barrington-Hotels-Wedding-Hotel.0-0-d110336-tWeddingHotel.Travel-Guide-Filter-Hotels) - [Great Barrington Hotels ](https://www.expedia.co.uk/Great-Barrington-Hotels.d110336.Travel-Guide-Hotels) - [Holiday Homes in Great Barrington ](https://www.expedia.co.uk/Great-Barrington-Private-Holiday-Homes.d110336-aaPrivateHolidayHomes.Travel-Guide-Accommodation) - [Hotels near Jacob's Pillow ](https://www.expedia.co.uk/Jacobs-Pillow-Hotels.0-l553248621532666599-0.Travel-Guide-Filter-Hotels) - [B&B in Lee ](https://www.expedia.co.uk/Lee-Bed-And-Breakfasts.d8572-aaBedAndBreakfasts.Travel-Guide-Accommodation) - [Hotels with Balcony in Lee ](https://www.expedia.co.uk/Lee-Hotels-Hotels-With-Balcony.0-0-d8572-tHotelswithBalcony.Travel-Guide-Filter-Hotels) - [Spa Hotels in Lee ](https://www.expedia.co.uk/Lee-Hotels-Spa-Hotels.0-0-d8572-tSpaHotels.Travel-Guide-Filter-Hotels) - [Lee Hotels ](https://www.expedia.co.uk/Lee-Hotels.d8572.Travel-Guide-Hotels) - [Adults Only Resorts & in Lenox ](https://www.expedia.co.uk/Lenox-Hotels-Adults-Only-Resorts.0-0-d8587-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Lenox ](https://www.expedia.co.uk/Lenox-Hotels-Budget-Hotels.0-0-d8587-tBudgetHotels.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in Lenox ](https://www.expedia.co.uk/Lenox-Hotels-Gay-Friendly-Hotel.0-0-d8587-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Hotels with Babysitting Services in Lenox ](https://www.expedia.co.uk/Lenox-Hotels-Hotel-With-Babysitting-Services.0-0-d8587-thotelwithbabysittingservices.Travel-Guide-Filter-Hotels) - [Hotels with Indoor Pools in Lenox ](https://www.expedia.co.uk/Lenox-Hotels-Hotels-With-Indoor-Pools.0-0-d8587-tHotelswithIndoorPools.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Lenox ](https://www.expedia.co.uk/Lenox-Hotels-Luxury-Hotel.0-0-d8587-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Hotels near Mahaiwe Performing Arts Center ](https://www.expedia.co.uk/Mahaiwe-Performing-Arts-Center-Hotels.0-l553248621532665242-0.Travel-Guide-Filter-Hotels) - [B&B in Monterey ](https://www.expedia.co.uk/Monterey-Bed-And-Breakfasts.d6005411-aaBedAndBreakfasts.Travel-Guide-Accommodation) - [Monterey Hotels ](https://www.expedia.co.uk/Monterey-Hotels.d6005411.Travel-Guide-Hotels) - [New Marlborough Hotels ](https://www.expedia.co.uk/New-Marlborough-Hotels.d137834.Travel-Guide-Hotels) - [Lodges in October Mountain State Forest ](https://www.expedia.co.uk/October-Mountain-State-Forest-Lodges.d6339856-aaLodges.Travel-Guide-Accommodation) - [Otis Hotels ](https://www.expedia.co.uk/Otis-Hotels.d6005412.Travel-Guide-Hotels) - [Cheap Hotels in Pittsfield ](https://www.expedia.co.uk/Pittsfield-Hotels-Budget-Hotels.0-0-d9478-tBudgetHotels.Travel-Guide-Filter-Hotels) - [Sheffield Hotels ](https://www.expedia.co.uk/Sheffield-Hotels.d157238.Travel-Guide-Hotels) - [Sherwood Forest Hotels ](https://www.expedia.co.uk/Sherwood-Forest-Becket-Hotels.0-n553248635976472129-0.Travel-Guide-Filter-Hotels) - [Beach Resorts & in South Egremont ](https://www.expedia.co.uk/South-Egremont-Hotels-Beach-Hotels.0-0-d183341-tBeachHotels.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in South Lee ](https://www.expedia.co.uk/South-Lee-Hotels-Adults-Only-Resorts.0-0-d183343-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [South Lee Hotels ](https://www.expedia.co.uk/South-Lee-Hotels.d183343.Travel-Guide-Hotels) - [Caravan Parks in Southfield ](https://www.expedia.co.uk/Southfield-Caravan-Parks.d6339785-aaCaravanParks.Travel-Guide-Accommodation) - [Southfield Hotels ](https://www.expedia.co.uk/Southfield-Hotels.d6339785.Travel-Guide-Hotels) - [Spa Hotels in Stockbridge ](https://www.expedia.co.uk/Stockbridge-Hotels-Spa-Hotels.0-0-d162575-tSpaHotels.Travel-Guide-Filter-Hotels) - [Stockbridge Hotels ](https://www.expedia.co.uk/Stockbridge-Hotels.d162575.Travel-Guide-Hotels) - [Gay-Friendly Hotels in West Stockbridge ](https://www.expedia.co.uk/West-Stockbridge-Hotels-Gay-Friendly-Hotel.0-0-d173346-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Flights to Great Barrington ](https://www.expedia.co.uk/Cheap-Flights-To-Great-Barrington.d110336.Travel-Guide-Flights) - [Flights to Lee ](https://www.expedia.co.uk/Cheap-Flights-To-Lee.d8572.Travel-Guide-Flights) - [Flights from Chester ](https://www.expedia.co.uk/lp/flights/6005399/flights-from-chester) - [Flights from Monterey ](https://www.expedia.co.uk/lp/flights/6005411/flights-from-monterey) - [Flights from Otis ](https://www.expedia.co.uk/lp/flights/6005412/flights-from-otis) - [Flights from Southfield ](https://www.expedia.co.uk/lp/flights/6339785/flights-from-southfield) - [Flights from Lee ](https://www.expedia.co.uk/lp/flights/8572/flights-from-lee) - [Visit Becket ](https://www.expedia.co.uk/Becket.dx6005395) - [Visit Blandford ](https://www.expedia.co.uk/Blandford.dx80625) - [Chester Holidays ](https://www.expedia.co.uk/Chester.d6005399.Holidays-City-Breaks) - [Great Barrington Holidays ](https://www.expedia.co.uk/Great-Barrington.d110336.Holidays-City-Breaks) - [Visit Great Barrington ](https://www.expedia.co.uk/Great-Barrington.dx110336) - [Housatonic River Walk ](https://www.expedia.co.uk/Housatonic-River-Walk-Great-Barrington.d553248621532665241.Attraction) - [Lake Mansfield Park ](https://www.expedia.co.uk/Lake-Mansfield-Park-Great-Barrington.d553248621560926695.Attraction) - [Magnolia Bluffs Casino ](https://www.expedia.co.uk/Magnolia-Bluffs-Casino-Sheffield.d553248621532644877.Attraction) - [Visit Mill River ](https://www.expedia.co.uk/Mill-River.dx3000748895) - [Monterey Holidays ](https://www.expedia.co.uk/Monterey.d6005411.Holidays-City-Breaks) - [Otis Holidays ](https://www.expedia.co.uk/Otis.d6005412.Holidays-City-Breaks) - [Visit Sandisfield ](https://www.expedia.co.uk/Sandisfield.dx6005416) - [Sheffield Holidays ](https://www.expedia.co.uk/Sheffield.d157238.Holidays-City-Breaks) - [Southfield Holidays ](https://www.expedia.co.uk/Southfield.d6339785.Holidays-City-Breaks) - [Ski Holiday Packages Great Barrington ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/110336/Great-Barrington) - [Alamo Rent A Car Rental Cars in Great Barrington ](https://www.expedia.co.uk/Alamo-Rent-A-Car-Car-Rentals-In-Great-Barrington.d110336-c6.Car-Rental-Guide-Suppliers) - [Budget Rental Cars in Great Barrington ](https://www.expedia.co.uk/Budget-Car-Rentals-In-Great-Barrington.d110336-c39.Car-Rental-Guide-Suppliers) - [Car hire Great Barrington ](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Great-Barrington.d110336.Car-Hire-Guide) - [Car hire Lee ](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Lee.d8572.Car-Hire-Guide) - [Car hire Sheffield ](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Sheffield.d157238.Car-Hire-Guide) - [Economy Car Hire in Great Barrington ](https://www.expedia.co.uk/Economy-Car-Rentals-In-Great-Barrington.d110336-tEconomy.Car-Rental-Guide-Class) - [Enterprise Rental Cars in Great Barrington ](https://www.expedia.co.uk/Enterprise-Car-Rentals-In-Great-Barrington.d110336-c15.Car-Rental-Guide-Suppliers) - [Fox Rental Cars Rental Cars in Great Barrington ](https://www.expedia.co.uk/Fox-Rental-Cars-Car-Rentals-In-Great-Barrington.d110336-c19.Car-Rental-Guide-Suppliers) - [Thai Cars Rental Cars in Great Barrington ](https://www.expedia.co.uk/Thai-Cars-Car-Rentals-In-Great-Barrington.d110336-c1027.Car-Rental-Guide-Suppliers) - [Becket Holiday Rentals ](https://www.expedia.co.uk/Becket-Holiday-Rentals.d6005395.Travel-Guide-HolidayRentals) - [Great Barrington Holiday Rentals ](https://www.expedia.co.uk/Great-Barrington-Holiday-Rentals.d110336.Travel-Guide-HolidayRentals) - [Lee Holiday Rentals ](https://www.expedia.co.uk/Lee-Holiday-Rentals.d8572.Travel-Guide-HolidayRentals) - [Monterey Holiday Rentals ](https://www.expedia.co.uk/Monterey-Holiday-Rentals.d6005411.Travel-Guide-HolidayRentals) - [Sheffield Holiday Rentals ](https://www.expedia.co.uk/Sheffield-Holiday-Rentals.d157238.Travel-Guide-HolidayRentals) - [Book Family-Friendly Hotels in The Berkshires on Expedia.com ](https://www.expedia.com/The-Berkshires-Hotels-Family-Hotel.0-0-d6047665-tFamilyHotel.Travel-Guide-Filter-Hotels)