Title: Book the Best Lenox WINERY Hotels in 2026 | Expedia.ca [Hotels in Lenox](https://expedia.ca/Lenox-Hotels.d8587.Travel-Guide-Hotels)[Vacation Rentals in Lenox](https://expedia.ca/Lenox-Vacation-Rentals.d8587.Travel-Guide-VacationRentals)[Flights to Lenox](https://expedia.ca/Cheap-Flights-To-Lenox.d8587.Travel-Guide-Flights)[Lenox Car Rentals](https://expedia.ca/Car-Rentals-In-Lenox.d8587.Car-Rental-Guide)[Lenox Vacation Packages](https://expedia.ca/Lenox.d8587.Destination-Travel-Guides) ![The Mount - Edith Wharton's Home - Lenox, Massachusetts](https://images.trvl-media.com/place/8587/61bc1452-d29a-4cc8-bf0a-1865d2683e8a.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/8587/61bc1452-d29a-4cc8-bf0a-1865d2683e8a.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Lenox Winery Hotels Tonight [Feb 3 - Feb 4](https://www.expedia.ca/Hotel-Search?regionId=8587&startDate=2026-02-03&endDate=2026-02-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 4 - Feb 5](https://www.expedia.ca/Hotel-Search?regionId=8587&startDate=2026-02-04&endDate=2026-02-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=8587&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=8587&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Lenox hotels with winery ![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/6a32b13e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/e459ce18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/53f3f179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) Lee 9.0/10 Wonderful (1,001 reviews) "Room was clean and the staff was super friendly and helpful!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ethan CA $133 CA $149 total includes taxes & fees Feb 23 - Feb 24 [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/75dbf9d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Double Room, 2 Queen Beds, Courtyard View](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/3d6dcf9e.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) ![Garden](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/b642a3ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### East Rock Inn [](https://www.expedia.ca/Great-Barrington-Hotels-East-Rock-Inn.h102806911.Hotel-Information) Great Barrington 9.6/10 Exceptional (37 reviews) "The room was clean and comfortable wi will back next year:) " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nadya CA $171 CA $192 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Great-Barrington-Hotels-East-Rock-Inn.h102806911.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](https://images.trvl-media.com/lodging/1000000/900000/894100/894066/648d8aa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/894100/894066/585313b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/1000000/900000/894100/894066/82d224a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Valley Inn [](https://www.expedia.ca/Williamstown-Hotels-Berkshire-Valley-Inn.h894066.Hotel-Information) Williamstown 9.2/10 Wonderful (566 reviews) "We had a short but pleasant stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Scott CA $171 CA $191 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Williamstown-Hotels-Berkshire-Valley-Inn.h894066.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/86910798.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) ![Loft, Private Bathroom (Skylight Loft)](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/a856ec31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/58d2b953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brook Farm Inn [](https://www.expedia.ca/Lenox-Hotels-Brook-Farm-Inn.h1196186.Hotel-Information) Lenox 9.4/10 Exceptional (164 reviews) "Everything was perfect - location and accommodation." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher [](https://www.expedia.ca/Lenox-Hotels-Brook-Farm-Inn.h1196186.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/69e879d6.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) ![Pilates](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/c06c6b54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/bd7aa934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gateways Inn & Restaurant [](https://www.expedia.ca/Lenox-Hotels-Gateways-Inn-Restaurant.h2519552.Hotel-Information) Lenox 8.0/10 Very good (197 reviews) "Gateways Inn is a fantastic place to stay! The staff was very courteous and the room was spacious and very clean. The breakfast was included and very tasty. I highly suggest a stay there if you are planning on visiting the Berkshires!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Miguel CA $218 CA $255 total includes taxes & fees Feb 4 - Feb 5 [](https://www.expedia.ca/Lenox-Hotels-Gateways-Inn-Restaurant.h2519552.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.ca/Hotel-Search?startDate=2026-02-17&endDate=2026-02-18®ionId=8587&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Lenox 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 "Immaculately clean and friendly staff. Easy parking and great breakfast" [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![The Cornell Inn, Lenox & The Berkshires](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/e8f22f38_y.jpg) ### The Cornell Inn, Lenox & The Berkshires 10/10 Excellent "Room was beautiful. Comfortable bed, excellent breakfast and a wonderful staff make this a great place for a weekend in Lenox. " [](https://expedia.ca/Lenox-Hotels-The-Cornell-Inn.h1634230.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 "The room and amenities were amazing. " [](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![Howard Johnson by Wyndham Lenox](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84_y.jpg) ### Howard Johnson by Wyndham Lenox 10/10 Excellent "The room was clean, comfortable and the staff was friendly. For those who are afraid of vermin, there was NO SIGNS whatsoever of either bugs or other vermin.. It was CLEAN. This is a place that is no frills, but for what you're paying for you get a lot, and a comfortable place to rest your head. We would absolutely go back when we're visiting the Pittsfield area." [](https://expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) ![Whistler's Inn Bed & Breakfast](https://images.trvl-media.com/lodging/2000000/1200000/1197600/1197581/17dab433_y.jpg) ### Whistler's Inn Bed & Breakfast 10/10 Excellent "We had a wonderful stay. We are so glad we chose this inn. The location is superb…a five-minute walk to the center of Lenox! It is a beautiful inn with a lot of charm, and the staff is warm and friendly. We loved our large room too! Definitely plan on staying here again when we come back to the area! " [](https://expedia.ca/Lenox-Hotels-Whistlers-Inn-Bed-Breakfast.h1197581.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [3 Star Hotels in Stockbridge ](https://www.expedia.ca/3Star-Stockbridge-Hotels.s30-0-d162575.Travel-Guide-Filter-Hotels) - [Hotels near Berkshire Botanical Garden ](https://www.expedia.ca/Berkshire-Botanical-Garden-Hotels.0-l553248621532665247-0.Travel-Guide-Filter-Hotels) - [Hotels near Chesterwood ](https://www.expedia.ca/Chesterwood-Hotels.0-l6091841-0.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Massachusetts ](https://www.expedia.ca/Destinations-In-Massachusetts-Hotel-With-Early-Check-In.0-0-d223-thotelwithearlycheckin.Hotel-Filter-Destinations) - [Hotels with a Lazy River in Massachusetts ](https://www.expedia.ca/Destinations-In-Massachusetts-Hotels-With-A-Lazy-River.0-0-d223-tHotelswithaLazyRiver.Hotel-Filter-Destinations) - [Hotels with Free Breakfast in Massachusetts ](https://www.expedia.ca/Destinations-In-Massachusetts-Hotels-With-Free-Breakfast.0-0-d223-tHotelswithFreeBreakfast.Hotel-Filter-Destinations) - 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