Title: Book the Best Lenox WINERY Hotels in 2025 | 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) ![Lenox showing autumn colours](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105609-Lenox.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Lenox, MA from CA $167 ![](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 [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=8587&startDate=2025-10-16&endDate=2025-10-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=8587&startDate=2025-10-17&endDate=2025-10-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=8587&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=8587&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Lenox 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) ![Non Lakeside Superior Room, 2 Queen beds](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/d3eea453.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) ![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 (1008) "Great Indian restaurant in the hotel!" CA $149 CA $167 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Loft, Private Bathroom (Skylight Loft)](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)](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)](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/c348a91f.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) ### Brook Farm Inn Lenox 9.4/10 Exceptional (161) "Inn was gorgeous and staff exceptional!" CA $239 CA $267 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Lenox-Hotels-Brook-Farm-Inn.h1196186.Hotel-Information) ![Room (King Room)](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/b5aaacce.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) ![Exterior](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/47826e47.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 (191) "Very well kept property, nice restaurant and is in a great area" CA $317 CA $370 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Lenox-Hotels-Gateways-Inn-Restaurant.h2519552.Hotel-Information) ![Premium Apartment | Private kitchen](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) ![1 bedroom, premium bedding, pillowtop 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) ![Premium Apartment | Living area](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/75dbf9d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### East Rock Inn Great Barrington 9.4/10 Exceptional (35) "Quiet and peaceful location set off the road, with woodsy area in the back. Very close to Main Street shops and restaurants. " CA $183 CA $205 total includes taxes & fees Nov 16 - Nov 17 [](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) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/894100/894066/5e7062a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/1000000/900000/894100/894066/15c28efa.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) ### Berkshire Valley Inn Williamstown 9.2/10 Wonderful (563) "We had a short but pleasant stay. " CA $233 CA $260 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Williamstown-Hotels-Berkshire-Valley-Inn.h894066.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/116000000/115470000/115470000/115469906/83d3f833_edited_d758.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 crib, 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." CA $228 CA $557 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/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/100000000/99250000/99243600/99243554/43b40eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/8de4c71d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/06261f5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/c3446830.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Near Tanglewood: Historic Summer Retreat New Lebanon 9.6/10 Exceptional (22) "Very cozy and comfortable with everything we needed to make our stay enjoyable. The kitchen was well stocked, the bedrooms a good size with comfortable mattresses. The deck and the yard were lovely. This location is gem!" CA $259 CA $578 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/New-Lebanon-Hotels-Near-Tanglewood-Historic-Summer-Retreat.h99243554.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!" CA $562 CA $932 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Clean-Free-Bagel-Shop.h92452756.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/33000000/32810000/32807400/32807378/e3e0e9fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/33000000/32810000/32807400/32807378/d9fe6b36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/33000000/32810000/32807400/32807378/52f8efbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/33000000/32810000/32807400/32807378/094a3cc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!! Valatie 10/10 Exceptional (54) "Great spot on the lake. Super quiet and relaxing." CA $379 CA $755 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Albany-Hotels-Escape-To-Lakefront-Leisurehudson.h32807378.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) ![Dining](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/w1424h960x16y0-bffb2a3a.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) ![TV, fireplace](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/0cd1f311.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy. Clean. Free bagel shop. 3 Fireplaces. Great Barrington CA $562 CA $932 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Clean-Free-Bagel-Shop-3-Fireplaces.h120045407.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=2025-10-30&endDate=2025-10-31®ionId=8587&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Lenox Hotel Reviews ![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 "Good breakfast King rooms are the best facing the mountains Recently remodeled " [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Howard Johnson by Wyndham Lenox](//images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84_y.jpg) ### Howard Johnson by Wyndham Lenox 10/10 Excellent "Good for the one night drive through! " [](https://expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) ![Wagon Wheel Inn](//images.trvl-media.com/lodging/2000000/1740000/1730200/1730144/75f1ed66_y.jpg) ### Wagon Wheel Inn 10/10 Excellent "Twas nicw" [](https://expedia.ca/Lenox-Hotels-Wagon-Wheel-Inn.h1730144.Hotel-Information) ![The Cornell Inn, Lenox & The Berkshires](//images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/e8f22f38_y.jpg) ### The Cornell Inn, Lenox & The Berkshires 10/10 Excellent "Very friendly staff. " [](https://expedia.ca/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information) ![Whistler's Inn Bed & Breakfast](//images.trvl-media.com/lodging/2000000/1200000/1197600/1197581/17dab433_y.jpg) ### Whistler's Inn Bed & Breakfast 10/10 Excellent "Unique design and decorations. Hot breakfast with muffins. Hosts Lisa, and Joan were terrific. " [](https://expedia.ca/Lenox-Hotels-Whistlers-Inn-Bed-Breakfast.h1197581.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." [](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![The Dewey](//images.trvl-media.com/lodging/6000000/5210000/5203000/5202927/7aa060b9_y.jpg) ### The Dewey 10/10 Excellent "Great spot. Lots of history. 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[Townhomes in South Lee](https://www.expedia.ca/South-Lee-Townhomes.d183343-aaTownhomes.Travel-Guide-Accommodation) - [B&B in Stockbridge](https://www.expedia.ca/Stockbridge-Bed-And-Breakfast.d162575-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Stockbridge](https://www.expedia.ca/Stockbridge-Guest-Houses.d162575-aaGuestHouses.Travel-Guide-Accommodation) - [Boutique Hotels in Stockbridge](https://www.expedia.ca/Stockbridge-Hotels-Boutique-Hotel.0-0-d162575-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Stockbridge](https://www.expedia.ca/Stockbridge-Hotels-Cheap-Hotels.0-0-d162575-tCheapHotels.Travel-Guide-Filter-Hotels) - [Historic Hotels in Stockbridge](https://www.expedia.ca/Stockbridge-Hotels-Historic-Hotel.0-0-d162575-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Stockbridge](https://www.expedia.ca/Stockbridge-Hotels-Luxury-Hotel.0-0-d162575-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Stockbridge](https://www.expedia.ca/Stockbridge-Hotels-Pet-Friendly-Hotel.0-0-d162575-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - 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[Spa Hotels in West Stockbridge](https://www.expedia.ca/West-Stockbridge-Hotels-Spa-Hotel.0-0-d173346-tSpaHotel.Travel-Guide-Filter-Hotels) - [West Stockbridge Hotels](https://www.expedia.ca/West-Stockbridge-Hotels.d173346.Travel-Guide-Hotels) - [Flights to Pittsfield](https://www.expedia.ca/Cheap-Flights-To-Pittsfield.d9478.Travel-Guide-Flights) - [Flights to Stockbridge](https://www.expedia.ca/Cheap-Flights-To-Stockbridge.d162575.Travel-Guide-Flights) - [Flights from Lee](https://www.expedia.ca/lp/flights/8572/flights-from-lee) - [Flights from Bangor (BGR) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/bgr/psf/bangor-to-pittsfield) - [Flights from Boston (BOS) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/bos/psf/boston-to-pittsfield) - [Flights from Ithaca (ITH) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/ith/psf/ithaca-to-pittsfield) - [Flights from Plattsburgh (PBG) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/pbg/psf/plattsburgh-to-pittsfield) - [Flights from Phoenix (PHX) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/phx/psf/phoenix-to-pittsfield) - [Flights from Richmond (RIC) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/ric/psf/richmond-to-pittsfield) - [Flights from Seattle (SEA) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/sea/psf/seattle-to-pittsfield) - [Flights from Toronto (YYZ) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/yyz/psf/toronto-to-pittsfield) - [Canoe Meadows Wildlife Sanctuary](https://www.expedia.ca/Canoe-Meadows-Wildlife-Sanctuary-Pittsfield.d553248621532665285.Vacation-Attraction) - [Hancock Shaker Village](https://www.expedia.ca/Hancock-Shaker-Village-Pittsfield.d6091849.Vacation-Attraction) - [Lenox Library](https://www.expedia.ca/Lenox-Library-Lenox.d553248621532665268.Vacation-Attraction) - [National Shrine of the Divine Mercy](https://www.expedia.ca/National-Shrine-Of-The-Divine-Mercy-Stockbridge.d553248621532665250.Vacation-Attraction) - [Naumkeag Museum](https://www.expedia.ca/Naumkeag-Museum-Stockbridge.d6091843.Vacation-Attraction) - [Norman Rockwell Museum](https://www.expedia.ca/Norman-Rockwell-Museum-Stockbridge.d6091839.Vacation-Attraction) - [Richmond Vacations](https://www.expedia.ca/Richmond.d151138.Destination-Travel-Guides) - [Visit South Lee](https://www.expedia.ca/South-Lee.dx183343) - [Visit Stockbridge](https://www.expedia.ca/Stockbridge.dx162575) - [Ventfort Hall Mansion and Gilded Age Museum](https://www.expedia.ca/Ventfort-Hall-Mansion-And-Gilded-Age-Museum-Lenox.d553248621532665270.Vacation-Attraction) - [Avis Rental Cars in Stockbridge](https://www.expedia.ca/Avis-Car-Rentals-In-Stockbridge.d162575-c41.Car-Rental-Guide-Suppliers) - [Car rental Lee](https://www.expedia.ca/Car-Rentals-In-Lee.d8572.Car-Rental-Guide) - [Rental cars Pittsfield Municipal airport](https://www.expedia.ca/Car-Rentals-In-Pittsfield-Municipal.d6031274.Car-Rental-Guide) - [Car rental Stockbridge](https://www.expedia.ca/Car-Rentals-In-Stockbridge.d162575.Car-Rental-Guide) - [Book Winery Hotels in Lenox on Expedia.com](https://www.expedia.com/Lenox-Hotels-Winery-Hotel.0-0-d8587-tWineryHotel.Travel-Guide-Filter-Hotels)