Title: Book the Best Western Massachusetts WINERY Hotels in 2025 | Expedia.ca [Western Massachusetts Travel Guide](https://expedia.ca/Western-Massachusetts.dx6234063)[Hotels in Western Massachusetts](https://expedia.ca/Western-Massachusetts-Hotels.d6234063.Travel-Guide-Hotels)[Vacation Rentals in Western Massachusetts](https://expedia.ca/Western-Massachusetts-Vacation-Rentals.d6234063.Travel-Guide-VacationRentals)[Flights to Western Massachusetts](https://expedia.ca/Cheap-Flights-To-Western-Massachusetts.d6234063.Travel-Guide-Flights)[Western Massachusetts Car Rentals](https://expedia.ca/Car-Rentals-In-Western-Massachusetts.d6234063.Car-Rental-Guide)[Western Massachusetts Vacation Packages](https://expedia.ca/Western-Massachusetts.d6234063.Destination-Travel-Guides) ![The Berkshires featuring snow as well as a family](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/71000/71827-The-Berkshires.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Western Massachusetts, MA ![](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 Western Massachusetts Winery Hotels Tonight [Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=6234063&startDate=2025-10-29&endDate=2025-10-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 30 - Oct 31](https://www.expedia.ca/Hotel-Search?regionId=6234063&startDate=2025-10-30&endDate=2025-10-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6234063&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6234063&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Western Massachusetts 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) ![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 (1000) "Great Indian restaurant in the hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris CA $148 CA $166 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/11000000/10270000/10260600/10260538/8fe97c17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/11000000/10270000/10260600/10260538/7c9d16de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10270000/10260600/10260538/5e340d73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/11000000/10270000/10260600/10260538/f6356fb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Springfield/Downtown South End 8.6/10 Excellent (1000) "wonderful and clean hotel. very nice room and comfortable bed" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Larissa CA $150 CA $170 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Springfield-Hotels-Hampton-Inn-Suites-Springfield-Downtown.h10260538.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/90293a2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/5c3a2624.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/8c645106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/bd8e0182.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott West Springfield West Springfield 9.2/10 Wonderful (553) "Room was clean and staff was super friendly " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessuca CA $165 CA $189 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Springfield-Hotels-Courtyard-By-Marriott-West-Springfield.h33298677.Hotel-Information) ![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/20000/17900/17876/fe4b5272.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/17900/17876/0d0e7da1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/20000/17900/17876/080950ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony Queen](https://images.trvl-media.com/lodging/1000000/20000/17900/17876/1845c2ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Northampton Northampton 9.2/10 Wonderful (1000) "Best place around, I would definitely recommend to anyone. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) James CA $1,254 CA $1,400 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Springfield-Hotels-Hotel-Northampton.h17876.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/cab085ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/a37fc75b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/8974a65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### D. Hotel Suites & Spa Holyoke 9.4/10 Exceptional (2269) "Very comfortable rooms. Excellent restaurant on site. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynette CA $153 CA $178 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) ![Deluxe Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/30000/24600/24588/f86e1269.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/24600/24588/08813197.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/30000/24600/24588/0244c317.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed, Non Smoking (Exterior Corridor)](https://images.trvl-media.com/lodging/1000000/30000/24600/24588/70487177.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn & Suites Northampton - Amherst Northampton 7.2/10 Good (1000) "Clean rooms , great breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sophie CA $167 CA $187 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Springfield-Hotels-Quality-Inn-Suites-Northampton-Amherst.h24588.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) ![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) ![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) ### Berkshire Valley Inn Williamstown 9.2/10 Wonderful (563) "We had a short but pleasant stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Scott CA $174 CA $195 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Williamstown-Hotels-Berkshire-Valley-Inn.h894066.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) ![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) ![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) ### 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 CA $219 CA $244 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Lenox-Hotels-Brook-Farm-Inn.h1196186.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/fbd2cba0.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) ### 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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda CA $184 CA $206 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Great-Barrington-Hotels-East-Rock-Inn.h102806911.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34090000/34080200/34080135/08d859c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, music library, video library](https://images.trvl-media.com/lodging/35000000/34090000/34080200/34080135/d59ece13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/35000000/34090000/34080200/34080135/c74cafb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34090000/34080200/34080135/73d09dd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Creation Station is a cozy place so make yourself at home. Easthampton Ma. 10/10 Exceptional (70) "This was our second time staying here and we had a great time!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andy L. CA $251 CA $374 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Easthampton-Hotels-The-Creation-Station-Is-A-Cozy-Place-So-Make-Yourself-At-Home.h34080135.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=2025-11-12&endDate=2025-11-13®ionId=6234063&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Western Massachusetts Hotel Reviews ![Quality Inn](//images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg) ### Quality Inn 10/10 Excellent "Clean and convenient. Great front desk help. " [](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.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 "Coffee maker looks like it has mold inside " [](https://expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [Beach Hotel Hotels in Cambridge](https://www.expedia.ca/Cambridge-Hotels-Beach-Hotel.0-0-d8093-tBeachHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Cambridge](https://www.expedia.ca/Cambridge-Hotels-Couples-Resorts-Hotels.0-0-d8093-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Cambridge](https://www.expedia.ca/Cambridge-Hotels-Hotel-With-Pool.0-0-d8093-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Winery Hotels in Cambridge](https://www.expedia.ca/Cambridge-Hotels-Winery-Hotel.0-0-d8093-tWineryHotel.Travel-Guide-Filter-Hotels) - 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