Title: TOP Winery Hotels in The Berkshires, MA for 2025 | 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 # Search Winery Hotels in The Berkshires - ![](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 Winery Hotels Tonight [27 Nov - 28 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2025-11-27&endDate=2025-11-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [28 Nov - 29 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2025-11-28&endDate=2025-11-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [28 Nov - 30 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [5 Dec - 7 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top The Berkshires Winery Hotels ![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) ![Miscellaneous](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17.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 Lee 9.0/10 Wonderful (1005) "The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elisabeth £90 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/48ea2807.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/eb4406db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Private Bathroom (Victorian Room) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/49947e81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Private Bathroom (Tanglewood Suite) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/c348a91f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brook Farm Inn Lenox 9.4/10 Exceptional (162) "Comfortable, quiet, convenient location, very friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan [](https://www.expedia.co.uk/Lenox-Hotels-Brook-Farm-Inn.h1196186.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/894100/894066/78b361f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/894100/894066/5e7062a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/894100/894066/16c514f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom | 1 bedroom, minibar, individually furnished, laptop workspace](https://images.trvl-media.com/lodging/1000000/900000/894100/894066/15c28efa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Valley Inn Williamstown 9.2/10 Wonderful (564) "We had a short but pleasant stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Scott £117 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Williamstown-Hotels-Berkshire-Valley-Inn.h894066.Hotel-Information) ![Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Private kitchen | Mini-fridge, microwave, electric kettle](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/61ae6bd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/fbd2cba0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/75dbf9d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/c0c5a00b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### East Rock Inn Great Barrington 9.4/10 Exceptional (36) "We had a great stay at East Rock Inn! Newly remodeled, clean room, comfortable bed, easy access to town. I will definitely stay there again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura £104 includes taxes & fees 11 Dec - 12 Dec [](https://www.expedia.co.uk/Great-Barrington-Hotels-East-Rock-Inn.h102806911.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/ecdea449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/4bbc4f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/51a25809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel cot, free WiFi](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/162d61f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake! Sherwood Forest 10/10 Exceptional (4) "We loved it! Lots of local hiking trails and a wonderful relaxing place." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharon K. £291 includes taxes & fees 1 Dec - 2 Dec [](https://www.expedia.co.uk/Becket-Hotels-Dog-Friendly-A-Frame-In-The-Berkshires-Walk-To-Lake-With-Beach-Access.h115469906.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103850000/103845900/103845853/e9c2fca2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/104000000/103850000/103845900/103845853/8250863a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/104000000/103850000/103845900/103845853/3d66f0f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103850000/103845900/103845853/930055e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer Great Barrington £287 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Great-Barrington-Hotels-Close-To-Tanglewood-2BR-King-Bed-Fireplace-Sleeps-6-Mountain-View-Gem.h103845853.Hotel-Information) ![Room (King Room) | Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/b5aaacce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/47826e47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/bbe2d3d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/ed32e5ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gateways Inn & Restaurant Lenox 8.0/10 Very good (192) "Very well kept property, nice restaurant and is in a great area" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Josephine £175 includes taxes & fees 4 Dec - 5 Dec [](https://www.expedia.co.uk/Lenox-Hotels-Gateways-Inn-Restaurant.h2519552.Hotel-Information) ![Premium bedding, memory-foam beds, individually decorated](https://images.trvl-media.com/lodging/58000000/57540000/57535200/57535178/c91ee1cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/58000000/57540000/57535200/57535178/ff622b2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, memory-foam beds, individually decorated](https://images.trvl-media.com/lodging/58000000/57540000/57535200/57535178/64920fe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/58000000/57540000/57535200/57535178/9c0b3e3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nautical Nest Hudson 9.6/10 Exceptional (123) "We had an amazing stay! What a lovely and comfortable room, conveniently situated to shopping & so many great dining options. The shared kitchen area was well-appreciated. We would definitely return again in the future. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robin £100 includes taxes & fees 1 Dec - 2 Dec [](https://www.expedia.co.uk/Hudson-Hotels-Nautical-Nest.h57535178.Hotel-Information) ![Room, 1 King Bed, Balcony, Garden View | Balcony view](https://images.trvl-media.com/lodging/12000000/11760000/11751500/11751478/d0c8bd3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Bathtub | Egyptian cotton sheets, premium bedding, pillow-top beds, minibar](https://images.trvl-media.com/lodging/12000000/11760000/11751500/11751478/1b76829a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Farm to table cuisine](https://images.trvl-media.com/lodging/12000000/11760000/11751500/11751478/a7fe15ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/12000000/11760000/11751500/11751478/0908fc0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wm. Farmer & Sons Hudson 9.2/10 Wonderful (73) "So beautifully preserved building. We had a beautiful room with sitting area overlooking the front of the hotel. Very easy to get to main streets and riverside. Restaurant was wonderful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vivienne £140 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Hudson-Hotels-Wm-Farmer-Sons-Boarding-And-Barroom.h11751478.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, pool loungers](https://images.trvl-media.com/lodging/92000000/91030000/91030000/91029901/a4bcd50d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, pool umbrellas, pool loungers](https://images.trvl-media.com/lodging/92000000/91030000/91030000/91029901/a09f4b1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91030000/91030000/91029901/e442bc31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily self-service breakfast ](https://images.trvl-media.com/lodging/92000000/91030000/91030000/91029901/122959c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Amelia Hudson 9.8/10 Exceptional (27) "Nice place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Manuel £391 includes taxes & fees 29 Nov - 30 Nov [](https://www.expedia.co.uk/Hudson-Hotels-The-Amelia.h91029901.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=2025-12-11&endDate=2025-12-12®ionId=6047665&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_FR-DE-MX-UK_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Save up to 40% on select hotels. [Book now](https://expedia.co.uk/cheap-deals?rfrr=AFFINITY_BF_PROMO_6047665) ## Top The Berkshires Hotel Reviews ![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 "This is our second time here and it was fantastic. Always super clean, great amenities,and staff is always nice and respectful. My fiance and I will be coming here once or twice a year, every year. Starting new tradition for my birthday. It is such a nice room to relax and enjoy each others company in comfort. " [](https://expedia.co.uk/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![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 "Yes" [](https://expedia.co.uk/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.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 "Good" [](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) - 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[Book Winery Hotels in The Berkshires on Expedia.com](https://www.expedia.com/The-Berkshires-Hotels-Winery-Hotel.0-0-d6047665-tWineryHotel.Travel-Guide-Filter-Hotels)