Title: TOP The Berkshires All-inclusive Hotels for 2026 - All Inclusive Resorts in The Berkshires, MA | 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 All-Inclusive 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 All-Inclusive Hotels Tonight [7 Dec - 8 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2025-12-07&endDate=2025-12-08&adults=2&amenities=ALL_INCLUSIVE&mealPlan=ALL_INCLUSIVE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [8 Dec - 9 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2025-12-08&endDate=2025-12-09&adults=2&amenities=ALL_INCLUSIVE&mealPlan=ALL_INCLUSIVE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [12 Dec - 14 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2025-12-12&endDate=2025-12-14&adults=2&amenities=ALL_INCLUSIVE&mealPlan=ALL_INCLUSIVE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [19 Dec - 21 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=ALL_INCLUSIVE&mealPlan=ALL_INCLUSIVE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top The Berkshires All-Inclusive Hotels ![Exterior](https://images.trvl-media.com/lodging/1000000/980000/973700/973618/bb582c2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/980000/973700/973618/eed56796.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/980000/973700/973618/f280eaf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private pool](https://images.trvl-media.com/lodging/1000000/980000/973700/973618/49db7134.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Club Wyndham Bentley Brook Hancock 9.2/10 Wonderful (565) "Good place to take your family." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria [](https://www.expedia.co.uk/Hancock-Hotels-Club-Wyndham-Bentley-Brook.h973618.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/a5e72142.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/w1290h860x0y968-0dd10b20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/7549d558.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/4a1f06eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Willows Motel Williamstown Williamstown 9.0/10 Wonderful (992) "Warm welcome. Great location. Best fresh fruit breakfast ever." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa £64 includes taxes & fees 8 Dec - 9 Dec [](https://www.expedia.co.uk/Williamstown-Hotels-Willows-Motel-Williamstown.h1753359.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/c64cd286.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) ![Standard Room, 2 Queen Beds | View from room](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/44b0e4d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maple Terrace Motel Williamstown 9.6/10 Exceptional (587) "Reception was great, lovely beds (most important to me), great location, this place is excellent." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William £83 includes taxes & fees 8 Dec - 9 Dec [](https://www.expedia.co.uk/Williamstown-Hotels-Maple-Terrace-Motel.h13278987.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) ![Superior Room, 1 King Bed, Jetted Tub | Jetted bathtub](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/f3c92221.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/f43c89bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed, Fireplace | Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/4ea5ab50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Yankee, Trademark Collection by Wyndham Lenox 9.2/10 Wonderful (1000) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ann £75 includes taxes & fees 14 Dec - 15 Dec [](https://www.expedia.co.uk/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Outdoor pool, pool loungers](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Firehouse) | Frette Italian sheets, hypo-allergenic bedding, desk, iron/ironing board](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/71ef2331.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Queen Beds (Main Inn) | Frette Italian sheets, hypo-allergenic bedding, desk, iron/ironing board](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/5f2e6b29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d969459c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Red Lion Inn Stockbridge 8.8/10 Excellent (1000) "I love the ambience - historic and comfortable and excellent food. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy £152 includes taxes & fees 5 Jan - 6 Jan 2026 [](https://www.expedia.co.uk/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.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) ![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 curtains](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a25612d3.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) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG Pittsfield 8.0/10 Very good (982) "Staff was very nice and helpful nice place restaurant was awesome great food and drinks" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frank £77 includes taxes & fees 12 Dec - 13 Dec [](https://www.expedia.co.uk/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/3e2c75da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, open 8:00 AM to 10:00 PM, pool loungers](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/ceca8706.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/e55e7242.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Berkshires-Lenox Lenox 9.2/10 Wonderful (1000) "Clean, pleasant staff and good breakfast. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edward £86 includes taxes & fees 14 Dec - 15 Dec [](https://www.expedia.co.uk/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/5fa17ca2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/1715f4d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![42-inch LCD TV with cable/satellite TV channels, TV, MP3 dock](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/8f88194e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/507a7437.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Lenox Pittsfield Pittsfield 9.2/10 Wonderful (657) "Clean and convenient to Mt. Greylock. Kind staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristen £86 includes taxes & fees 14 Dec - 15 Dec [](https://www.expedia.co.uk/Pittsfield-Hotels-Hilton-Garden-Inn-Lenox-Pittsfield.h10246064.Hotel-Information) ![Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/fa93cb94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/a1ad800b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/83dd2b57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/44ab9667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Monument Mountain Motel Great Barrington 9.0/10 Wonderful (803) "Yes it was clean & staff was very polite. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara L. [](https://www.expedia.co.uk/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information) ![Front of property – evening/night](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds | In-room safe, desk, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/c60f19d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/d48c4129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/f3e43c7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Williams Inn Williamstown 9.6/10 Exceptional (546) "Clean,heating was noisy,bed was to soft,shower head dripped. Very friendly and helpful staff.good breakfast!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jon £159 includes taxes & fees 8 Dec - 9 Dec [](https://www.expedia.co.uk/Williamstown-Hotels-The-Williams-Inn.h35658765.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=2025-12-21&endDate=2025-12-22®ionId=6047665&adults=2&mealPlan=ALL_INCLUSIVE&sort=RECOMMENDED&openPlayBack=true) ## Find out more about The Berkshires ### Discover top The Berkshires attractions The Berkshires, a stunning region in western Massachusetts, offers an array of activities perfect for travellers seeking all-inclusive hotel experiences. Begin your adventure at the renowned Tanglewood, the summer home of the Boston Symphony Orchestra, where you can enjoy world-class music performances amid the serene landscape. Enjoy the picturesque scenery while indulging in gourmet picnics provided by your hotel, with local delicacies like artisanal cheeses and fresh produce. Next, explore the enchanting hiking trails of Mount Greylock, the highest peak in Massachusetts, where breathtaking views await. Your all-inclusive stay may offer guided hikes or wellness programmes, providing both adventure and relaxation. For art lovers, the Norman Rockwell Museum showcases the iconic works of the beloved American artist, and many hotels in the area feature art-themed packages, including exclusive tours and workshops. Don't miss the opportunity to unwind at one of the local spas, where your all-inclusive accommodation might include rejuvenating treatments using local ingredients. Finally, the charming town of Stockbridge offers delightful shops and restaurants, making it an ideal base. With luxurious amenities and attentive service in your all-inclusive hotel, explore the rich cultural heritage while indulging in delicious farm-to-table dining experiences, ensuring a memorable family getaway. ## Top The Berkshires Hotel Reviews ## 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) - 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