Title: Book the Best Southeast Massachusetts WINERY Hotels in 2025 | Expedia.ca [Southeast Massachusetts Travel Guide](https://expedia.ca/Southeast-Massachusetts.dx6047675)[Hotels in Southeast Massachusetts](https://expedia.ca/Southeast-Massachusetts-Hotels.d6047675.Travel-Guide-Hotels)[Vacation Rentals in Southeast Massachusetts](https://expedia.ca/Southeast-Massachusetts-Vacation-Rentals.d6047675.Travel-Guide-VacationRentals)[Flights to Southeast Massachusetts](https://expedia.ca/Cheap-Flights-To-Southeast-Massachusetts.d6047675.Travel-Guide-Flights)[Things to do in Southeast Massachusetts](https://expedia.ca/Things-To-Do-In-Southeast-Massachusetts.d6047675.Travel-Guide-Activities)[Southeast Massachusetts Car Rentals](https://expedia.ca/Car-Rentals-In-Southeast-Massachusetts.d6047675.Car-Rental-Guide)[Southeast Massachusetts Vacation Packages](https://expedia.ca/Southeast-Massachusetts.d6047675.Destination-Travel-Guides) ![Jenney Grist Mill featuring a house and a river or creek](https://images.trvl-media.com/place/6262784/c962adcf-cee3-4ae2-9e4a-9096f8d77bb3.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Southeast Massachusetts from CA $141 - ![](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 Southeast Massachusetts Winery Hotels Tonight [Nov 28 - Nov 29](https://www.expedia.ca/Hotel-Search?regionId=6047675&startDate=2025-11-28&endDate=2025-11-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 29 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=6047675&startDate=2025-11-29&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=6047675&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=6047675&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Southeast 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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/e74c9a7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, 1 King Bed](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/9874775f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chatham Wayside Inn Chatham 9.2/10 Wonderful (592) "We loved staying here! Our room was spacious, clean, quiet and very well maintained. The hotel is beautiful and a perfect location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Beth CA $195 CA $280 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.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) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/9100/9001/ff635628.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) ![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) ### Hotel 1620 Plymouth Harbor Plymouth Cultural District 8.2/10 Very good (1006) "Great stay clean friendly and kids loved splash pad and pool!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard [](https://www.expedia.ca/Plymouth-Hotels-Hotel-1620-Plymouth-Harbor.h9001.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/15000000/14850000/14845000/14844940/2287ecde.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) ![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) ### Frederick William House Falmouth 9.6/10 Exceptional (292) "Beat B&B i have ever stayed at! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Philip CA $205 CA $234 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Falmouth-Hotels-Frederick-William-House.h14844940.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/490000/480800/480770/75730e05.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) ### Uncommoner Hotel by Reverie Boutique Collection West Yarmouth 9.4/10 Exceptional (94) "Great staff, beautiful property" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Margaret CA $143 CA $164 total includes taxes & fees Dec 10 - Dec 11 [](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) ![Exterior](https://images.trvl-media.com/lodging/77000000/76930000/76923100/76923089/a2d5704f.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) ![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 (185) "Great place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sandra CA $126 CA $141 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/East-Wareham-Hotels-The-Inn-Onset.h76923089.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) ![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) ![Room, 1 Queen Bed](https://images.trvl-media.com/lodging/13000000/12430000/12426900/12426891/1c660188.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Village Inn Cape Cod Yarmouth Port 10/10 Exceptional (222) "It was so charming, would definitely stay there again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kyle CA $237 CA $271 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Yarmouth-Port-Hotels-The-Village-Inn-Cape-Cod.h12426891.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/116000000/115550000/115546000/115545914/a83d5a17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/116000000/115550000/115546000/115545914/bdbdfe6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115550000/115546000/115545914/9f66402e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115550000/115546000/115545914/7d5db133.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 1-bedroom apartment in fabulous Provincetown Provincetown 9.6/10 Exceptional (4) "This is definitely the place you want to book when staying in PTown. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark P. CA $105 CA $241 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Provincetown-Hotels-Charming-1-Bedroom-Apartment-In-Fabulous-Provincetown.h115545914.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) ![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 sitting area](https://images.trvl-media.com/lodging/1000000/70000/65700/65623/bbd479b1.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) ### Faraway Martha's Vineyard Edgartown 9.0/10 Wonderful (1007) "Just a neat place to stay, very nice place. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stuart [](https://www.expedia.ca/Edgartown-Hotels-Faraway-Marthas-Vineyard.h65623.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/41000000/40290000/40283500/40283414/bab152c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/41000000/40290000/40283500/40283414/7e1e24c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/41000000/40290000/40283500/40283414/49d1d00f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/41000000/40290000/40283500/40283414/d9225b26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK Chatham 9.6/10 Exceptional (101) "Our second year in a row staying here. Cute house and great location! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erin M. CA $125 CA $572 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Chatham-Hotels-Quaint-Chatham-Home-Wbeautiful-Backyard-Furnished-Multi-Level-Deck.h40283414.Hotel-Information) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/83000000/82960000/82955300/82955212/b95a3937.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/83000000/82960000/82955300/82955212/7d33e498.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/83000000/82960000/82955300/82955212/c988dcc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/83000000/82960000/82955300/82955212/45685c8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Steps from Marina, beach, restaurants! Wareham 9.8/10 Exceptional (12) "Beautiful space, wonderful location, amazing host. If I could give 100 stars I would! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jaimie CA $125 CA $329 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Buzzards-Bay-Hotels-Private-Suite-Steps-From-Marina.h82955212.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=2025-12-12&endDate=2025-12-13®ionId=6047675&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_6047675) ## Top Southeast Massachusetts Hotel Reviews ![Faraway Martha's Vineyard](https://images.trvl-media.com/lodging/1000000/70000/65700/65623/10e4fb42_y.jpg) ### Faraway Martha's Vineyard 10/10 Excellent "Overall excellence" [](https://expedia.ca/Edgartown-Hotels-Faraway-Marthas-Vineyard.h65623.Hotel-Information) ![Hyannis Travel Inn](https://images.trvl-media.com/lodging/2000000/1380000/1379200/1379109/fe11d49f_y.jpg) ### Hyannis Travel Inn 10/10 Excellent "Yes, it was very nice. The staff was helpful. " [](https://expedia.ca/Hyannis-Hotels-Hyannis-Travel-Inn.h1379109.Hotel-Information) ![Hotel 1620 Plymouth Harbor](https://images.trvl-media.com/lodging/1000000/10000/9100/9001/2f69f9a1_y.jpg) ### Hotel 1620 Plymouth Harbor 10/10 Excellent "Great stay clean friendly and kids loved splash pad and pool!" [](https://expedia.ca/Plymouth-Hotels-Hotel-1620-Plymouth-Harbor.h9001.Hotel-Information) ![Cape Sands Inn](https://images.trvl-media.com/lodging/2000000/1340000/1330200/1330174/aa954682_y.jpg) ### Cape Sands Inn 10/10 Excellent "Clean room, great rate easy checkin and easy checkout. Will stay again. " [](https://expedia.ca/West-Yarmouth-Hotels-Cape-Sands-Inn.h1330174.Hotel-Information) ![Falmouth Inn](https://images.trvl-media.com/lodging/1000000/900000/893200/893142/a26689a2_y.jpg) ### Falmouth Inn 10/10 Excellent "Clean room. Nice staff, convenient location. We enjoyed a drink and live music at the restaurant attached." [](https://expedia.ca/Falmouth-Hotels-Falmouth-Inn.h893142.Hotel-Information) ![Margaritaville Resort Cape Cod](https://images.trvl-media.com/lodging/1000000/20000/12900/12897/b57e0b1f_y.jpg) ### Margaritaville Resort Cape Cod 10/10 Excellent "The room were clean. The staff were all friendly! I will definitely go back!!! 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[Book Winery Hotels in Southeast Massachusetts on Expedia.com](https://www.expedia.com/Southeast-Massachusetts-Hotels-Winery-Hotel.0-0-d6047675-tWineryHotel.Travel-Guide-Filter-Hotels)