Title: Book the Best Eastern Massachusetts WINERY Hotels in 2025 | Expedia.ca [Eastern Massachusetts Travel Guide](https://expedia.ca/Eastern-Massachusetts.dx6234158)[Hotels in Eastern Massachusetts](https://expedia.ca/Eastern-Massachusetts-Hotels.d6234158.Travel-Guide-Hotels)[Vacation Rentals in Eastern Massachusetts](https://expedia.ca/Eastern-Massachusetts-Vacation-Rentals.d6234158.Travel-Guide-VacationRentals)[Flights to Eastern Massachusetts](https://expedia.ca/Cheap-Flights-To-Eastern-Massachusetts.d6234158.Travel-Guide-Flights)[Things to do in Eastern Massachusetts](https://expedia.ca/Things-To-Do-In-Eastern-Massachusetts.d6234158.Travel-Guide-Activities)[Eastern Massachusetts Car Rentals](https://expedia.ca/Car-Rentals-In-Eastern-Massachusetts.d6234158.Car-Rental-Guide)[Eastern Massachusetts Vacation Packages](https://expedia.ca/Eastern-Massachusetts.d6234158.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/475000/475485-Boston.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Eastern Massachusetts ![](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 Eastern Massachusetts Winery Hotels Tonight [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=6234158&startDate=2025-10-14&endDate=2025-10-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=6234158&startDate=2025-10-15&endDate=2025-10-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6234158&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=6234158&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Eastern Massachusetts Winery Hotels ![Beach nearby](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/1adc0002.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/f436a6d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/471fd6ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/e74c9a7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chatham Wayside Inn Chatham 9.2/10 Wonderful (572) "Great hotel, great locatiion" CA $213 CA $301 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/15000000/14850000/14845000/14844940/9df3839f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/15000000/14850000/14845000/14844940/9f04984c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/15000000/14850000/14845000/14844940/2287ecde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/15000000/14850000/14845000/14844940/ccc11328.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Frederick William House Falmouth 9.6/10 Exceptional (290) "Beat B&B i have ever stayed at! " CA $207 CA $237 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Falmouth-Hotels-Frederick-William-House.h14844940.Hotel-Information) ![Suite, Balcony, Pool View](https://images.trvl-media.com/lodging/1000000/10000/9100/9001/2f69f9a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/1000000/10000/9100/9001/cef4c177.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/1000000/10000/9100/9001/495721b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/10000/9100/9001/a56eb119.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel 1620 Plymouth Harbor Plymouth Downtown Waterfront District 8.2/10 Very good (1007) "Great location, excellent staff, good value." CA $209 CA $276 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Plymouth-Hotels-Hotel-1620-Plymouth-Harbor.h9001.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/15000000/14770000/14763200/14763138/6ed01d7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace Apartment | View from room](https://images.trvl-media.com/lodging/15000000/14770000/14763200/14763138/8a34403c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/15000000/14770000/14763200/14763138/86a55b3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/15000000/14770000/14763200/14763138/b28b2f57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kingfisher Harwich Port Harwich Port 9.0/10 Wonderful (35) "We had a wonderful stay ! The room was clean, comfortable, and well-maintained — everything we needed for a relax stay! " CA $315 CA $361 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Harwich-Port-Hotels-Seadar-Inn-By-The-Sea.h14763138.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/13000000/12430000/12426900/12426891/00d26354.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/13000000/12430000/12426900/12426891/c14b1773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![32-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/13000000/12430000/12426900/12426891/2b1f0d40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/13000000/12430000/12426900/12426891/6a955bb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Village Inn Cape Cod Yarmouth Port 10/10 Exceptional (221) "Jennifer is a wonderful host! Breakfast on the back porch was delicious and a great start to the day. Rooms are comfortable and the back of the house where we were was, is quiet. Highly recommend. " CA $237 CA $271 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Yarmouth-Port-Hotels-The-Village-Inn-Cape-Cod.h12426891.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/1000000/490000/480800/480770/76dbfadf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/490000/480800/480770/10f6fac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gift shop](https://images.trvl-media.com/lodging/1000000/490000/480800/480770/ff5be5db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![VISIONARY KING ELITE](https://images.trvl-media.com/lodging/1000000/490000/480800/480770/82541975.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Uncommoner Hotel by Reverie Boutique Collection West Yarmouth 9.2/10 Wonderful (68) "Such a nice place to stay for a weekend getaway, we will definitely be back!" CA $169 CA $194 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/West-Yarmouth-Hotels-Tidewater-Inn.h480770.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/77000000/76930000/76923100/76923089/cbba8a4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Queen Bed | Courtyard view](https://images.trvl-media.com/lodging/77000000/76930000/76923100/76923089/6ceaa2ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76930000/76923100/76923089/a2d5704f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bay View King Bed | Living area](https://images.trvl-media.com/lodging/77000000/76930000/76923100/76923089/cfe97e12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn on Onset Bay East Wareham 8.4/10 Very good (180) "Great place to stay " CA $126 CA $141 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/East-Wareham-Hotels-The-Inn-Onset.h76923089.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/90000000/89400000/89399300/89399258/90b2a5a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, coffee/tea maker](https://images.trvl-media.com/lodging/90000000/89400000/89399300/89399258/88b3e715.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/90000000/89400000/89399300/89399258/84d00fd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Studio, 2 Queen Beds](https://images.trvl-media.com/lodging/90000000/89400000/89399300/89399258/d9561f18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Beverly Beverly 8.4/10 Very good (358) "Clean room Easy check in. Walkable to Salem Nice hotel overall. Will definitely stay again " CA $196 CA $219 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Boston-Hotels-The-Beverly.h89399258.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/70000/65700/65623/10e4fb42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/70000/65700/65623/c5b09697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/70000/65700/65623/bbd479b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 8:00 AM to 8:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/70000/65700/65623/w3997h1139x0y0-c751d22f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Faraway Martha's Vineyard Edgartown 9.0/10 Wonderful (1007) "Just a neat place to stay, very nice place. " CA $297 CA $348 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Edgartown-Hotels-Faraway-Marthas-Vineyard.h65623.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/700000/690700/690647/35d4ab15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, blackout drapes, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/700000/690700/690647/d4b92a2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/700000/690700/690647/5d9bbf95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/700000/690700/690647/1961153a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Points by Sheraton Boston Logan Airport Revere Revere 8.0/10 Very good (1004) "Lovely little bar, convenient location, happy for shuttle to airport." CA $175 CA $196 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Boston-Hotels-Four-Points-By-Sheraton-Boston-Logan-Airport-Revere.h690647.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=2025-10-28&endDate=2025-10-29®ionId=6234158&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Eastern Massachusetts Hotel Reviews ![Wyndham Boston Beacon Hill](//images.trvl-media.com/lodging/1000000/30000/25700/25655/fa173b31_y.jpg) ### Wyndham Boston Beacon Hill 10/10 Excellent "Centrally located." 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