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 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 1 - Oct 2](https://www.expedia.ca/Hotel-Search?regionId=6234063&startDate=2025-10-01&endDate=2025-10-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 2 - Oct 3](https://www.expedia.ca/Hotel-Search?regionId=6234063&startDate=2025-10-02&endDate=2025-10-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6234063&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6234063&startDate=2025-10-10&endDate=2025-10-12&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!" CA $153 CA $171 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.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) ![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) ![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) ### D. Hotel Suites & Spa Holyoke 9.4/10 Exceptional (2256) "Best hotel option for the Easthampton area hands down. " CA $153 CA $178 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/10200/10167/5b0e9d46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/10200/10167/3b3a01ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/10200/10167/18ceeab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, soundproofing](https://images.trvl-media.com/lodging/1000000/20000/10200/10167/647159c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Sturbridge - Brimfield Sturbridge 9.0/10 Wonderful (1001) "Convenient location " CA $150 CA $168 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Sturbridge-Hotels-Comfort-Inn-Suites-Sturbridge-Brimfield.h10167.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) ![Exterior](https://images.trvl-media.com/lodging/11000000/10270000/10260600/10260538/5e340d73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/11000000/10270000/10260600/10260538/d91e9d99.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) ### Hampton Inn & Suites Springfield/Downtown South End 8.6/10 Excellent (1002) "Staff was so friendly and the hotel was so clean! " CA $170 CA $193 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Springfield-Hotels-Hampton-Inn-Suites-Springfield-Downtown.h10260538.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/24600/24588/08813197.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/30000/24600/24588/daff17af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn & Suites Northampton - Amherst Northampton 7.2/10 Good (1000) "great location - just off the highway and near to downtown" CA $176 CA $197 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Springfield-Hotels-Quality-Inn-Suites-Northampton-Amherst.h24588.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/103000000/102810000/102807000/102806911/22135a72.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 (32) "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. " CA $204 CA $228 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Great-Barrington-Hotels-East-Rock-Inn.h102806911.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) ![Lobby](https://images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/bd8e0182.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/eaa5d51b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott West Springfield West Springfield 9.0/10 Wonderful (533) "The hotel is wonderful and located close to shopping and some nice local restaurants. The staff was very attentive and thoughtful." CA $188 CA $215 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Springfield-Hotels-Courtyard-By-Marriott-West-Springfield.h33298677.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) ![Shared kitchen](https://images.trvl-media.com/lodging/58000000/57540000/57535200/57535178/838315b8.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) ### Nautical Nest Hudson 9.6/10 Exceptional (120) "Great location. Room needs a comfy chair" CA $207 CA $241 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Hudson-Hotels-Nautical-Nest.h57535178.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1080000/1074400/1074390/5dc7d6d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/2000000/1080000/1074400/1074390/1cbdfdde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 1 Queen Bed with Sofa bed | Private kitchen](https://images.trvl-media.com/lodging/2000000/1080000/1074400/1074390/dca364d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1080000/1074400/1074390/a4ff04b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence Inn by Marriott Hartford Avon Avon 8.8/10 Excellent (404) "Staff was great" CA $177 CA $203 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Hartford-Hotels-Residence-Inn-By-Marriott-Hartford-Avon.h1074390.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) ![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)](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/49947e81.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) ### Brook Farm Inn Lenox 9.4/10 Exceptional (161) "Inn was gorgeous and staff exceptional!" CA $237 CA $265 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Lenox-Hotels-Brook-Farm-Inn.h1196186.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=2025-10-16&endDate=2025-10-17®ionId=6234063&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Western Massachusetts Hotel Reviews ## 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) - [Apartments in Chesterfield](https://www.expedia.ca/Chesterfield-Apartments.d89029-aaApartments.Travel-Guide-Accommodation) - 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