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://a.travel-assets.com/findyours-php/viewfinder/images/res70/71000/71831-The-Berkshires.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 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 [12 Oct - 13 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2025-10-12&endDate=2025-10-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [13 Oct - 14 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2025-10-13&endDate=2025-10-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [17 Oct - 19 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [24 Oct - 26 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6047665&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top The Berkshires Winery Hotels ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/588051f1.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9.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 (1006) "Great Indian restaurant in the hotel!" £89 includes taxes & fees 2 Nov - 3 Nov [](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) ![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) ![Porch](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/eb4406db.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 (161) "Inn was gorgeous and staff exceptional!" [](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) ![Deluxe Triple Room | 1 bedroom, minibar, individually furnished, laptop workspace](https://images.trvl-media.com/lodging/1000000/900000/894100/894066/648d8aa4.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 (563) "We had a short but pleasant stay. " £138 includes taxes & fees 6 Nov - 7 Nov [](https://www.expedia.co.uk/Williamstown-Hotels-Berkshire-Valley-Inn.h894066.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) ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/1274c274.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gateways Inn & Restaurant Lenox 8.0/10 Very good (191) "Very well kept property, nice restaurant and is in a great area" £213 includes taxes & fees 3 Nov - 4 Nov [](https://www.expedia.co.uk/Lenox-Hotels-Gateways-Inn-Restaurant.h2519552.Hotel-Information) ![Premium Apartment | Private kitchen | Electric kettle](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/61ae6bd3.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) ![Exterior](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/22135a72.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) ### East Rock Inn Great Barrington 9.4/10 Exceptional (33) "Room was really comfortable and clean. Beautiful views from the main court yard during the day and at night the sky was full of stars. Amazing. " £110 includes taxes & fees 3 Nov - 4 Nov [](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) ![Exterior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/51a25809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/83d3f833_edited_d758.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! Walk to lake with beach access! Sherwood Forest 10/10 Exceptional (3) "We loved it! Lots of local hiking trails and a wonderful relaxing place." £305 includes taxes & fees 28 Oct - 29 Oct [](https://www.expedia.co.uk/Becket-Hotels-Dog-Friendly-A-Frame-In-The-Berkshires-Walk-To-Lake-With-Beach-Access.h115469906.Hotel-Information) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/93000000/92460000/92452800/92452756/4d036f9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/93000000/92460000/92452800/92452756/581ea0b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/93000000/92460000/92452800/92452756/e6b4678e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/93000000/92460000/92452800/92452756/725d323d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy. Clean. Free bagel shop. Great Barrington 10/10 Exceptional (10) "The perfect location for a stay in Great Barrington. The house is so well done and very comfortable!" £508 includes taxes & fees 4 Nov - 5 Nov [](https://www.expedia.co.uk/Great-Barrington-Hotels-Cozy-Clean-Free-Bagel-Shop.h92452756.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/9eeeead4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/4f2c31bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/6873f6f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/w1424h960x16y0-bffb2a3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy. Clean. Free bagel shop. 3 Fireplaces. Great Barrington £508 includes taxes & fees 4 Nov - 5 Nov [](https://www.expedia.co.uk/Great-Barrington-Hotels-Cozy-Clean-Free-Bagel-Shop-3-Fireplaces.h120045407.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) ![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) ![Shared kitchen](https://images.trvl-media.com/lodging/58000000/57540000/57535200/57535178/838315b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nautical Nest Hudson 9.6/10 Exceptional (120) "Perfect location. " £138 includes taxes & fees 12 Nov - 13 Nov [](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) ![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) ![Room, 1 King Bed, Bathtub | 1 bedroom, Egyptian cotton sheets, premium bedding, pillow-top beds](https://images.trvl-media.com/lodging/12000000/11760000/11751500/11751478/1b76829a.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 (65) "Very nice stay " £168 includes taxes & fees 29 Oct - 30 Oct [](https://www.expedia.co.uk/Hudson-Hotels-Wm-Farmer-Sons-Boarding-And-Barroom.h11751478.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=2025-10-26&endDate=2025-10-27®ionId=6047665&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top The Berkshires Hotel Reviews ![Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires](//images.trvl-media.com/lodging/1000000/920000/913200/913175/1d50a551_y.jpg) ### Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires 10/10 Excellent "The property is very nice and the staff was extremely friendly and helpful." [](https://expedia.co.uk/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](//images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "Great location, very clean!" [](https://expedia.co.uk/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Best Western Plus Berkshire Hills Inn & Suites](//images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg) ### Best Western Plus Berkshire Hills Inn & Suites 10/10 Excellent "Clean place. Good breakfast and friendly staff" [](https://expedia.co.uk/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![Hampton Inn & Suites Berkshires-Lenox](//images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg) ### Hampton Inn & Suites Berkshires-Lenox 10/10 Excellent "Felt comfortable and safe. Nice pool and gym facility." 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[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 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)