Title: Massachusetts Winery Hotels from CA $195: Book the Right Winery Hotels Room in Massachusetts, United States of America - Expedia.ca [Massachusetts Travel Guide](https://expedia.ca/Massachusetts.dx223)[Massachusetts Hotels](https://expedia.ca/Destinations-In-Massachusetts.d223.Hotel-Destinations)[Vacation Rentals in Massachusetts](https://expedia.ca/Destinations-In-Massachusetts.d223.Vacation-Rental-Destinations)[Massachusetts Flights](https://expedia.ca/Destinations-In-Massachusetts.d223.Flight-Destinations)[Massachusetts Car Rentals](https://expedia.ca/Destinations-In-Massachusetts.d223.Car-Rental-Destinations)[Massachusetts Vacations](https://expedia.ca/Massachusetts.d223.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/223/15b716aa-7bcd-4985-a9a4-b76daf9495af.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Massachusetts Winery Hotels from CA $195 - ![](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 ## Top Cities in Massachusetts ![](https://mediaim.expedia.com/destination/1/8bd66a7ae7636691016dd57f41ee8c80.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Oak Bluffs [](https://expedia.ca/Oak-Bluffs-Hotels-Winery-Hotel.0-0-d140231-tWineryHotel.Travel-Guide-Filter-Hotels) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/475000/475491-Boston.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Boston [](https://expedia.ca/Boston-Hotels-Winery-Hotel.0-0-d178239-tWineryHotel.Travel-Guide-Filter-Hotels) ![Nantucket showing a marina, central business district and a house](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/26000/26131-Nantucket.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Nantucket [](https://expedia.ca/Nantucket-Hotels-Winery-Hotel.0-0-d285-tWineryHotel.Travel-Guide-Filter-Hotels) ![Springfield which includes a city, a high-rise building and a bridge](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63440-Springfield-Western-Massachusetts.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Springfield [](https://expedia.ca/Springfield-Hotels-Winery-Hotel.0-0-d6047669-tWineryHotel.Travel-Guide-Filter-Hotels) ![Plymouth which includes shopping](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105337-Southeast-Massachusetts.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Plymouth [](https://expedia.ca/Plymouth-Hotels-Winery-Hotel.0-0-d9512-tWineryHotel.Travel-Guide-Filter-Hotels) ![Worcester featuring a fountain, modern architecture and night scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/80000/80021-Worcester-Mass.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Worcester [](https://expedia.ca/Worcester-Hotels-Winery-Hotel.0-0-d6023336-tWineryHotel.Travel-Guide-Filter-Hotels) ![Hyannis showing a marina and a bay or harbour](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105114-Cape-Cod.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Hyannis [](https://expedia.ca/Hyannis-Hotels-Winery-Hotel.0-0-d1544-tWineryHotel.Travel-Guide-Filter-Hotels) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/531000/531387-gloucester.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Gloucester [](https://expedia.ca/Gloucester-Hotels-Winery-Hotel.0-0-d8008-tWineryHotel.Travel-Guide-Filter-Hotels) ## Check availability on Massachusetts Winery Hotels Tonight [Nov 25 - Nov 26](https://www.expedia.ca/Hotel-Search?regionId=223&startDate=2025-11-25&endDate=2025-11-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 26 - Nov 27](https://www.expedia.ca/Hotel-Search?regionId=223&startDate=2025-11-26&endDate=2025-11-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=223&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=223&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Massachusetts Winery Hotels ![View from property](https://images.trvl-media.com/lodging/3000000/2190000/2182100/2182094/e86ce24b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2190000/2182100/2182094/f30d9b9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/3000000/2190000/2182100/2182094/04588712.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2190000/2182100/2182094/b950a23c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mansion House Inn And Spa Vineyard Haven 9.4/10 Exceptional (1003) "My wife and I loved our stay here. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Keith CA $245 CA $294 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Vineyard-Haven-Hotels-Mansion-House-Inn-And-Spa.h2182094.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/5000000/4560000/4555100/4555042/01f382c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's play area - outdoor](https://images.trvl-media.com/lodging/5000000/4560000/4555100/4555042/97bc0509.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/5000000/4560000/4555100/4555042/d82cfe07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Double Room](https://images.trvl-media.com/lodging/5000000/4560000/4555100/4555042/0351d881.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mariner Motel Falmouth 8.6/10 Excellent (1000) "Beautiful room, great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephanie CA $196 CA $224 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/Falmouth-Hotels-Mariner-Motel.h4555042.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/10000/9953/27ed2889.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/10000/9953/aa02dacb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/10000/10000/9953/78ad9652.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch served; American cuisine, alfresco dining ](https://images.trvl-media.com/lodging/1000000/10000/10000/9953/w1280h882x0y8-1138e6a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn on the Square Falmouth 8.6/10 Excellent (1009) "Great location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $141 CA $195 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Falmouth-Hotels-Inn-On-The-Square.h9953.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) ![Serves lunch and dinner](https://images.trvl-media.com/lodging/1000000/70000/65700/65623/e4e4c240.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/70000/65700/65623/c5b09697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Faraway Martha's Vineyard Edgartown 9.0/10 Wonderful (1005) "Just a neat place to stay, very nice place. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stuart CA $273 CA $320 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Edgartown-Hotels-Faraway-Marthas-Vineyard.h65623.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/1000000/10000/8600/8504/7b9d68f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, pool umbrellas](https://images.trvl-media.com/lodging/1000000/10000/8600/8504/b242e02b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/10000/8600/8504/3c648f42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/1000000/10000/8600/8504/7c321ede.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harbor View Hotel Edgartown 8.8/10 Excellent (1000) "The area was safe and the dining experience was great. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Albert [](https://www.expedia.ca/Edgartown-Hotels-Harbor-View-Hotel.h8504.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/1000000/900000/893200/893142/a26689a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/1000000/900000/893200/893142/c832e252.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Accessible](https://images.trvl-media.com/lodging/1000000/900000/893200/893142/339f4ae9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/900000/893200/893142/5c705214.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Falmouth Inn Falmouth 8.0/10 Very good (1003) "Clean room, good shower and helpful staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark CA $146 CA $196 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Falmouth-Hotels-Falmouth-Inn.h893142.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/60000/55000/54945/741b5772.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 2 Queen Beds](https://images.trvl-media.com/lodging/1000000/60000/55000/54945/b017dd76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/60000/55000/54945/3225f1fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/55000/54945/0271fbcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyannis Harbor Hotel Hyannis 8.0/10 Very good (1004) "Very clean, staff friendly and all amenities were great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joao CA $153 CA $233 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Hyannis-Hotels-Hyannis-Harbor-Hotel.h54945.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/1000000/20000/12200/12163/d9e8dd7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/20000/12200/12163/d37ab9f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/1000000/20000/12200/12163/a643a6cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12200/12163/6ef2f9a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel Edgartown 8.4/10 Very good (593) "Super comfortable bed and great linens and towels. Quiet and next door to grocery store. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) mary CA $240 CA $270 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Edgartown-Hotels-Edgar-Hotel-Marthas-Vineyard.h12163.Hotel-Information) ![Beach nearby, beach towels](https://images.trvl-media.com/lodging/10000000/9790000/9780600/9780586/0c92aeab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/10000000/9790000/9780600/9780586/ca8f5f5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Boating](https://images.trvl-media.com/lodging/10000000/9790000/9780600/9780586/c0436ae3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/10000000/9790000/9780600/9780586/3613e1ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pequot Hotel Oak Bluffs 9.4/10 Exceptional (572) "Location was perfect No TV reception.. and room was small but comfortable" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) robert [](https://www.expedia.ca/Oak-Bluffs-Hotels-Pequot-Hotel.h9780586.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/12000000/11180000/11172600/11172592/d11aa513.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11180000/11172600/11172592/d6b2594e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 1 Queen Bed with Sofa bed | Private kitchen](https://images.trvl-media.com/lodging/12000000/11180000/11172600/11172592/d22dc480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, 1 King Bed with Sofa bed | Private kitchen](https://images.trvl-media.com/lodging/12000000/11180000/11172600/11172592/430aaed8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Lightkeepers Inn Edgartown 9.4/10 Exceptional (209) "Great hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Benjamin [](https://www.expedia.ca/Edgartown-Hotels-The-Lightkeepers-Inn.h11172592.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=2025-12-09&endDate=2025-12-10®ionId=223&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AFFINITY_BF_PROMO_223) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Massachusetts-Winery-Hotel.0-0-d223-tWineryHotel.Hotel-Filter-Destinations)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Massachusetts-Winery-Hotel.0-0-d223-tWineryHotel.Hotel-Filter-Destinations) ## Top Massachusetts Hotel Reviews ![Copley Square Hotel, a FOUND Hotel](https://images.trvl-media.com/lodging/1000000/20000/16100/16067/72cd2881_y.jpg) ### Copley Square Hotel, a FOUND Hotel 10/10 Excellent "Room was very clean. Bed was very comfortable. Excellent location. " [](https://expedia.ca/Boston-Hotels-Copley-Square-Hotel.h16067.Hotel-Information) ![Seaport Hotel Boston](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg) ### Seaport Hotel Boston 10/10 Excellent "Staff are so kind" [](https://expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) ![Wyndham Boston Beacon Hill](https://images.trvl-media.com/lodging/1000000/30000/25700/25655/fa173b31_y.jpg) ### Wyndham Boston Beacon Hill 10/10 Excellent "Need good coffee" [](https://expedia.ca/Boston-Hotels-Wyndham-Boston-Beacon-Hill.h25655.Hotel-Information) ![citizenM Boston Back Bay](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/90056141_y.jpg) ### citizenM Boston Back Bay 10/10 Excellent "All the above! Location is great and the barista lounge and morning brunch is wonder ful and the staff terrific!! We will be back soon! " [](https://expedia.ca/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information) ![Encore Boston Harbor](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/9dbd3cd5_y.jpg) ### Encore Boston Harbor 10/10 Excellent "best stay ever! absolutely spotless great service and awesome amenities! " [](https://expedia.ca/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information) ![Omni Parker House ](https://images.trvl-media.com/lodging/1000000/30000/23500/23415/c414a1f3_y.jpg) ### Omni Parker House 10/10 Excellent "My three daughter's and I came down for a show and the Omni was within walking distance from everything. We had a wonderful time and will be back!" [](https://expedia.ca/Boston-Hotels-Boston-Omni-Parker-House-Hotel.h23415.Hotel-Information) ![Hampton Inn Boston - Logan Airport](https://images.trvl-media.com/lodging/1000000/580000/578500/578419/w3839h2488x0y0-d5429574_y.jpg) ### Hampton Inn Boston - Logan Airport 10/10 Excellent "Room was clean and beds were comfortable. Front desk and shuttle bus drivers were extremely helpful and kind. Shuttle service was excellent to train station and airport. BREAKFAST BAR was not the best. Fresh food would be nice over powdered eggs and waffle bar. Dining area had dirty tables and floors. Overall the hotel was comfortable and staff was attentive and helpful. We would stsy here again. aBrairport!" [](https://expedia.ca/Boston-Hotels-Hampton-Inn-Boston-Logan-Airport.h578419.Hotel-Information) ![The Dagny Boston](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg) ### The Dagny Boston 10/10 Excellent "Fabulous " [](https://expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) ![Harborside Inn Of Boston](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/b3140789_y.jpg) ### Harborside Inn Of Boston 10/10 Excellent "Great location. Clean Rooms. Comfortable bed. 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