Title: TOP Luxury Hotels in The Berkshires, MA for 2026 - The Berkshires Upscale 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 ![](https://images.trvl-media.com/place/6047665/e95ad08c-cd3f-48ea-b01c-31171bbd50b7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Luxury Hotels Tonight [15 Feb - 16 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2026-02-15&endDate=2026-02-16&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [16 Feb - 17 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2026-02-16&endDate=2026-02-17&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [20 Feb - 22 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2026-02-20&endDate=2026-02-22&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) In two weeks [27 Feb - 1 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2026-02-27&endDate=2026-03-01&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Our top choices for The Berkshires luxury hotels ![Suite, Private Bathroom (RedBird Suite) | View from room](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/a6ceeb05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast ](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/w3000h1988x0y3-ae06d912.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/2e09a8f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Private Bathroom (Parlour Suite) | Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/d4b17f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood [](https://www.expedia.co.uk/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) Stockbridge 9.2/10 Wonderful (110 reviews) "Great breakfast, friendly helpful staff, pretty yard, good location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah £274 includes taxes & fees 28 Feb - 1 Mar [](https://www.expedia.co.uk/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/8800/8739/9f24830b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down duvets, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/8800/8739/192c9e5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/1000000/10000/8800/8739/c234a028.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee service](https://images.trvl-media.com/lodging/1000000/10000/8800/8739/c7a35aa5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Orchards Hotel [](https://www.expedia.co.uk/Williamstown-Hotels-The-Orchards-Hotel.h8739.Hotel-Information) Williamstown 8.6/10 Excellent (442 reviews) "A little dated. Restaurant shut down for renovations, disappointing" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller [](https://www.expedia.co.uk/Williamstown-Hotels-The-Orchards-Hotel.h8739.Hotel-Information) ![Gazebo](https://images.trvl-media.com/lodging/12000000/11540000/11537600/11537599/ed0acf17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Jetted Tub | Rollaway beds, free WiFi, bed sheets](https://images.trvl-media.com/lodging/12000000/11540000/11537600/11537599/8ea10947.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/12000000/11540000/11537600/11537599/7b898eb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/12000000/11540000/11537600/11537599/7b1e7c82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lantern House Motel [](https://www.expedia.co.uk/Great-Barrington-Hotels-Lantern-House-Motel.h11537599.Hotel-Information) Great Barrington 8.2/10 Very good (455 reviews) "The fact that they require a vaccine card should be mentioned in their Hotels.com profile. Luckily for me I had it in my car. I don't mind if some hotel owners want to require it, but it should be pretty clearly stated. The owner told me that I didn't need to use the air conditioner, that I should open the windows. How about I decide that? The room was musty-smelling, and everything was very dated and just didn't feel very clean. There are better options in Great Barrington. This is a place to... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen [](https://www.expedia.co.uk/Great-Barrington-Hotels-Lantern-House-Motel.h11537599.Hotel-Information) ![Double Room | View from room](https://images.trvl-media.com/lodging/2000000/1740000/1730200/1730144/2f62b663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed (Jaccuzzi) | Jetted bathtub](https://images.trvl-media.com/lodging/2000000/1740000/1730200/1730144/d981b422.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free self-parking](https://images.trvl-media.com/lodging/2000000/1740000/1730200/1730144/46ab504c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1740000/1730200/1730144/75f1ed66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wagon Wheel Inn [](https://www.expedia.co.uk/Lenox-Hotels-Wagon-Wheel-Inn.h1730144.Hotel-Information) Lenox 7.0/10 Good (641 reviews) "Clean, comfortable older motel. Not fancy but a good place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Woodrow [](https://www.expedia.co.uk/Lenox-Hotels-Wagon-Wheel-Inn.h1730144.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/ef3ce5c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/e57afaf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/3ef861f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Library Suite, 1 King Bed | Premium bedding, minibar, in-room safe, desk](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/c5c7040f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel On North [](https://www.expedia.co.uk/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) Pittsfield 9.6/10 Exceptional (823 reviews) "Great staff, beautiful hotel. Would definitely recommend " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shawn £122 includes taxes & fees 19 Feb - 20 Feb [](https://www.expedia.co.uk/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![Miscellaneous](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/39fc54d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/54079ee2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/530107d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/b07cfd29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1896 House Country Inn & Motels [](https://www.expedia.co.uk/Williamstown-Hotels-1896-House-Country-Inn-Motels.h18670223.Hotel-Information) Williamstown 6.6/10 (448 reviews) "Place was convenient, cleaned and quiet a little old, but all in all a good stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelley [](https://www.expedia.co.uk/Williamstown-Hotels-1896-House-Country-Inn-Motels.h18670223.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Room, 1 King Bed, Non Smoking | Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/dbcc78d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, 1 King Bed, Jetted Tub | Jetted bathtub](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/8cd694d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool, pool loungers](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/3f4a1adf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Yankee, Trademark Collection by Wyndham [](https://www.expedia.co.uk/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) Lenox 9.2/10 Wonderful (1,004 reviews) "Very friendly staff comfy beds!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Giselle £76 includes taxes & fees 23 Feb - 24 Feb [](https://www.expedia.co.uk/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/6d051282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Double Room | Blackout curtains, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/db3c3dee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deep-soaking bathtub](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/14870b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/049cb490.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunset Inn [](https://www.expedia.co.uk/Lee-Hotels-Sunset-Inn.h3025486.Hotel-Information) Lee 7.6/10 Good (411 reviews) "owners was nice, room was clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) tom £76 includes taxes & fees 16 Feb - 17 Feb [](https://www.expedia.co.uk/Lee-Hotels-Sunset-Inn.h3025486.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/1076a408.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, pool loungers](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/92f285fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property – evening/night](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/f3854c71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/25f05b7c.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 (596 reviews) "Cute place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa £81 includes taxes & fees 18 Feb - 19 Feb [](https://www.expedia.co.uk/Williamstown-Hotels-Maple-Terrace-Motel.h13278987.Hotel-Information) ![In-room safe, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/17f29286.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gazebo](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/20495b9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/7062b6be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Howard Johnson by Wyndham Lenox [](https://www.expedia.co.uk/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) Lenox 7.6/10 Good (831 reviews) "Clean room and the bed was very comfortable " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Arlan £56 includes taxes & fees 16 Feb - 17 Feb [](https://www.expedia.co.uk/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.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=2026-03-01&endDate=2026-03-02®ionId=6047665&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-uk-fr-de.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Holiday Sale Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save. [Book now](https://expedia.co.uk/cheap-deals?rfrr=AFFINITY_SPRING_PROMO_6047665) ## Find out more about The Berkshires ### The Berkshiresand its attractions for luxury travelers The Berkshires, a picturesque region in Massachusetts, offers a wealth of luxurious experiences for the discerning traveller. Begin your journey at Tanglewood, the summer home of the Boston Symphony Orchestra, where you can enjoy world-class performances under the stars while surrounded by the stunning natural beauty of the Berkshire hills. For art enthusiasts, the Norman Rockwell Museum in Stockbridge showcases the beloved works of America’s favourite illustrator, providing a glimpse into the cultural heart of the region. Those seeking relaxation can indulge in the serene atmosphere of Canyon Ranch, a wellness resort that offers spa treatments, fitness classes, and gourmet dining focused on health and well-being. For outdoor adventurers, the expansive hiking trails at Mount Greylock State Reservation promise breathtaking views, particularly in autumn when the foliage is ablaze with colour. Finally, indulge your palate at the acclaimed restaurants in Lenox, where farm-to-table dining experiences await, featuring the best local and seasonal ingredients. For a truly luxurious stay, consider the enchanting bluestone buildings of the Wheatleigh Hotel, a former Gilded Age mansion, where attentive service and elegant rooms make for an unforgettable retreat. ## Top The Berkshires Hotel Reviews ![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 "Fairly clean and staff were friendly" [](https://expedia.co.uk/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Quality Inn](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg) ### Quality Inn 10/10 Excellent "Clean room, great location" [](https://expedia.co.uk/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.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 "Spotless and front desk staff...friendly and accommodating " [](https://expedia.co.uk/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.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 "Bathroom had somebody’s hair on the door and shower " [](https://expedia.co.uk/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "Room was spotless, staff was amazing! Loved the bathroom setup! Will recommend and stay again! " [](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 "Traveling during freezing temperatures was a challenge but once we arrived at the Yankee Inn, we felt welcome and comfortable. Pre check-in was easy and our room was clean and warm and cozy. We ordered in and were told there were tables on the 2nd floor outside the breakfast room where we could eat our dinner. All the staff were friendly and helpful. An easy choice whenever we return to the area." [](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 "Clean room, friendly staff, and a delicious breakfast. The sauna was a wonderful surprise on a frigid day. We were grateful to find an EV charger at the inn. (They could use a couple more of them!)" [](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 "The staff was very nice. The breakfast very good. Comfortable bed. Adjustable temperature." [](https://expedia.co.uk/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.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 "Great place, room was clean and spacious. Breakfast time could last a little longer though, ending time was 9:30am, maybe extending until 11am is best. But overall was great. " [](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 Luxury Hotels in The Berkshires on Expedia.com ](https://www.expedia.com/The-Berkshires-Hotels-Luxury-Hotel.0-0-d6047665-tLuxuryHotel.Travel-Guide-Filter-Hotels)