Title: Book the Best Southeast Massachusetts WINERY Hotels in 2026 | 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) ![Southeast Massachusetts featuring fishing, a river or creek and autumn leaves](https://images.trvl-media.com/place/6047675/e509df6e-5c7b-43dd-9e29-15c54ef7f75c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6047675/e509df6e-5c7b-43dd-9e29-15c54ef7f75c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Jan 27 - Jan 28](https://www.expedia.ca/Hotel-Search?regionId=6047675&startDate=2026-01-27&endDate=2026-01-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 28 - Jan 29](https://www.expedia.ca/Hotel-Search?regionId=6047675&startDate=2026-01-28&endDate=2026-01-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6047675&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6047675&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Southeast Massachusetts hotels with winery ![Beach nearby](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/1adc0002.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/2000000/1520000/1517300/1517204/97707902.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) ![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) ### Chatham Wayside Inn [](https://www.expedia.ca/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.Hotel-Information) Chatham 9.2/10 Wonderful (623 reviews) "Yes, lovely place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela CA $162 CA $245 total includes taxes & fees Jan 28 - Jan 29 [](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) ![Staircase](https://images.trvl-media.com/lodging/1000000/10000/9100/9001/cef4c177.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Water park](https://images.trvl-media.com/lodging/1000000/10000/9100/9001/e4a36f56.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 [](https://www.expedia.ca/Plymouth-Hotels-Hotel-1620-Plymouth-Harbor.h9001.Hotel-Information) Plymouth Downtown Waterfront District 8.2/10 Very good (1,004 reviews) "Great place to go with family :)" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lymichelle [](https://www.expedia.ca/Plymouth-Hotels-Hotel-1620-Plymouth-Harbor.h9001.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/15000000/14850000/14845000/14844940/642c704c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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/e7d27f51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/15000000/14850000/14845000/14844940/216d8c41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Frederick William House [](https://www.expedia.ca/Falmouth-Hotels-Frederick-William-House.h14844940.Hotel-Information) Falmouth 9.6/10 Exceptional (296 reviews) "Beat B&B i have ever stayed at! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Philip CA $202 CA $232 total includes taxes & fees Feb 16 - Feb 17 [](https://www.expedia.ca/Falmouth-Hotels-Frederick-William-House.h14844940.Hotel-Information) ![Indoor pool, seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/490000/480800/480770/056f2544.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) ![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) ![Bicycling](https://images.trvl-media.com/lodging/1000000/490000/480800/480770/6ac8a051.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Uncommoner Hotel by Reverie Boutique Collection [](https://www.expedia.ca/West-Yarmouth-Hotels-Tidewater-Inn.h480770.Hotel-Information) West Yarmouth 9.4/10 Exceptional (103 reviews) "Clean, nice staff, good amenities, central location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Malbis CA $161 CA $185 total includes taxes & fees Jan 30 - Jan 31 [](https://www.expedia.ca/West-Yarmouth-Hotels-Tidewater-Inn.h480770.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/13000000/12430000/12426900/12426891/ae47522f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/13000000/12430000/12426900/12426891/023eb077.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Multiple Beds](https://images.trvl-media.com/lodging/13000000/12430000/12426900/12426891/19b90fe2.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) ### The Village Inn Cape Cod [](https://www.expedia.ca/Yarmouth-Port-Hotels-The-Village-Inn-Cape-Cod.h12426891.Hotel-Information) Yarmouth Port 10/10 Exceptional (224 reviews) "It was so charming, would definitely stay there again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kyle CA $213 CA $243 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Yarmouth-Port-Hotels-The-Village-Inn-Cape-Cod.h12426891.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2800000/2796200/2796134/0678b292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2800000/2796200/2796134/1678d73c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2800000/2796200/2796134/400bb244.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/3000000/2800000/2796200/2796134/26470c3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Delano Homestead Bed & Breakfast [](https://www.expedia.ca/Fairhaven-Hotels-Delano-Homestead-Bed-Breakfast.h2796134.Hotel-Information) Fairhaven 9.6/10 Exceptional (161 reviews) "It was a wonderful stay. Highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hye-Won CA $164 CA $184 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Fairhaven-Hotels-Delano-Homestead-Bed-Breakfast.h2796134.Hotel-Information) ![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) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/41000000/40290000/40283500/40283414/f8355c29.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) ![Exterior](https://images.trvl-media.com/lodging/41000000/40290000/40283500/40283414/e4387afe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK [](https://www.expedia.ca/Chatham-Hotels-Quaint-Chatham-Home-Wbeautiful-Backyard-Furnished-Multi-Level-Deck.h40283414.Hotel-Information) Chatham 9.6/10 Exceptional (102 reviews) "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 $122 CA $577 total includes taxes & fees Jan 31 - Feb 1 [](https://www.expedia.ca/Chatham-Hotels-Quaint-Chatham-Home-Wbeautiful-Backyard-Furnished-Multi-Level-Deck.h40283414.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107620000/107619200/107619161/971b5951.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107620000/107619200/107619161/57687b0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107620000/107619200/107619161/ae8432cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, music library](https://images.trvl-media.com/lodging/108000000/107620000/107619200/107619161/b561c4a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brayton Point Beach Bungalow in Somerset Massachusetts [](https://www.expedia.ca/Somerset-Hotels-Brayton-Point-Beach-Bungalow-In-Somerset-Massachusetts.h107619161.Hotel-Information) Somerset 10/10 Exceptional (4 reviews) "Brilliant house. Everything we needed was there. Area was quiet, lovely setting. Amazing hosts made us feel at home." ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Ann R. CA $199 CA $312 total includes taxes & fees Feb 11 - Feb 12 [](https://www.expedia.ca/Somerset-Hotels-Brayton-Point-Beach-Bungalow-In-Somerset-Massachusetts.h107619161.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/73000000/72440000/72435000/72434954/c5192e69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, Netflix, books](https://images.trvl-media.com/lodging/73000000/72440000/72435000/72434954/c100b426.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, Netflix, books](https://images.trvl-media.com/lodging/73000000/72440000/72435000/72434954/a58600d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, Netflix, books](https://images.trvl-media.com/lodging/73000000/72440000/72435000/72434954/1fed40da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail [](https://www.expedia.ca/Brewster-Hotels-Cheery-House-Wdeck.h72434954.Hotel-Information) West Brewster 9.6/10 Exceptional (50 reviews) "House was perfect for our family reunion! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gregg H. CA $181 CA $735 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Brewster-Hotels-Cheery-House-Wdeck.h72434954.Hotel-Information) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/89000000/88190000/88181300/88181254/ad69d0eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/89000000/88190000/88181300/88181254/ff7cf345.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/89000000/88190000/88181300/88181254/8d910532.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/89000000/88190000/88181300/88181254/05cf438c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy three-bedroom home close to Boston w/ plenty of parking [](https://www.expedia.ca/Boston-Hotels-Cozy-Three-Bedroom-Home-Close-To-Boston-W-Plenty-Of-Parking.h88181254.Hotel-Information) North Braintree 10/10 Exceptional (44 reviews) "The house was just what we needed and the stay was super simple. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris B. CA $239 CA $582 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Boston-Hotels-Cozy-Three-Bedroom-Home-Close-To-Boston-W-Plenty-Of-Parking.h88181254.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=2026-02-10&endDate=2026-02-11®ionId=6047675&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Southeast Massachusetts Hotel Reviews ![Chatham Bars Inn](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/w5700h3895x0y5-016d240d_y.jpg) ### Chatham Bars Inn 10/10 Excellent "Beautiful property " [](https://expedia.ca/Chatham-Hotels-Chatham-Bars-Inn.h19139.Hotel-Information) ![Falmouth Inn](https://images.trvl-media.com/lodging/1000000/900000/893200/893142/a26689a2_y.jpg) ### Falmouth Inn 10/10 Excellent "I stay here alot" [](https://expedia.ca/Falmouth-Hotels-Falmouth-Inn.h893142.Hotel-Information) ![John Carver Inn & Spa](https://images.trvl-media.com/lodging/7000000/6590000/6589100/6589076/4f9cc923_y.jpg) ### John Carver Inn & Spa 10/10 Excellent "The Inn is in the middle of a renovation. We stayed in one of the rooms that had renovations completed. The new room theme was nice. The kids loved the arcade and the pool area as well. Will be back for sure!" [](https://expedia.ca/Plymouth-Hotels-John-Carver-Inn-Spa.h6589076.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 "Front desk staff was so friendly check in was a breeze. " [](https://expedia.ca/Plymouth-Hotels-Hotel-1620-Plymouth-Harbor.h9001.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 "Evrything is so clean! We love staying here with our family with small children. The kids love it and so do we! We go back every year. It's become a tradition! " [](https://expedia.ca/Hyannis-Hotels-Cape-Codder-Resort-And-Spa.h12897.Hotel-Information) ![Faraway Martha's Vineyard](https://images.trvl-media.com/lodging/1000000/70000/65700/65623/10e4fb42_y.jpg) ### Faraway Martha's Vineyard 10/10 Excellent "Very cozy comfortable hotel!!" 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