Title: TOP Winery Hotels in Southeast Massachusetts for 2026 | Expedia.co.uk [Southeast Massachusetts Travel Guide](https://expedia.co.uk/Southeast-Massachusetts.dx6047675)[Hotels in Southeast Massachusetts](https://expedia.co.uk/Southeast-Massachusetts-Hotels.d6047675.Travel-Guide-Hotels)[Holiday Rentals in Southeast Massachusetts](https://expedia.co.uk/Southeast-Massachusetts-Holiday-Rentals.d6047675.Travel-Guide-HolidayRentals)[Flights to Southeast Massachusetts](https://expedia.co.uk/Cheap-Flights-To-Southeast-Massachusetts.d6047675.Travel-Guide-Flights)[Things to do in Southeast Massachusetts](https://expedia.co.uk/Things-To-Do-In-Southeast-Massachusetts.d6047675.Travel-Guide-Activities)[Southeast Massachusetts Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Southeast-Massachusetts.d6047675.Car-Hire-Guide)[Southeast Massachusetts Holidays](https://expedia.co.uk/Southeast-Massachusetts.d6047675.Holidays-City-Breaks) ![National Monument to the Forefathers featuring a statue or sculpture](https://images.trvl-media.com/place/6091769/545d4b07-afa1-46d5-b6a8-78324e701bd5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6091769/545d4b07-afa1-46d5-b6a8-78324e701bd5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](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 [17 Jan - 18 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=6047675&startDate=2026-01-17&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [18 Jan - 19 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=6047675&startDate=2026-01-18&endDate=2026-01-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [23 Jan - 25 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=6047675&startDate=2026-01-23&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [30 Jan - 1 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=6047675&startDate=2026-01-30&endDate=2026-02-01&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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/0ed95706.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.co.uk/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.Hotel-Information) Chatham 9.2/10 Wonderful (615 reviews) "Yes, lovely place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela £134 includes taxes & fees 21 Jan - 22 Jan [](https://www.expedia.co.uk/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.Hotel-Information) ![Suite, Balcony, Pool View | Hypo-allergenic bedding, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/1000000/10000/9100/9001/2f69f9a1.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) ![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 [](https://www.expedia.co.uk/Plymouth-Hotels-Hotel-1620-Plymouth-Harbor.h9001.Hotel-Information) Plymouth Downtown Waterfront District 8.2/10 Very good (1,001 reviews) "Great place to go with family :)" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lymichelle [](https://www.expedia.co.uk/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) ![Terrace/patio](https://images.trvl-media.com/lodging/15000000/14850000/14845000/14844940/3d82ccd1.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) ![Dining](https://images.trvl-media.com/lodging/15000000/14850000/14845000/14844940/9df3839f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Frederick William House [](https://www.expedia.co.uk/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 £126 includes taxes & fees 16 Feb - 17 Feb [](https://www.expedia.co.uk/Falmouth-Hotels-Frederick-William-House.h14844940.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) ![Room, Multiple Beds | 1 bedroom, premium bedding, down duvets, individually decorated](https://images.trvl-media.com/lodging/13000000/12430000/12426900/12426891/19b90fe2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/13000000/12430000/12426900/12426891/03e2796f.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.co.uk/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 £133 includes taxes & fees 21 Jan - 22 Jan [](https://www.expedia.co.uk/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.co.uk/Fairhaven-Hotels-Delano-Homestead-Bed-Breakfast.h2796134.Hotel-Information) Fairhaven 9.6/10 Exceptional (160 reviews) "The B&B was beautifully maintained. Breakfast was terrific. Highly recommended. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donald £100 includes taxes & fees 19 Jan - 20 Jan [](https://www.expedia.co.uk/Fairhaven-Hotels-Delano-Homestead-Bed-Breakfast.h2796134.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) ![Voyager Escape King Elite | Premium bedding, pillow-top beds, in-room safe, individually decorated](https://images.trvl-media.com/lodging/1000000/490000/480800/480770/c366b6b8.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) ### Uncommoner Hotel by Reverie Boutique Collection [](https://www.expedia.co.uk/West-Yarmouth-Hotels-Tidewater-Inn.h480770.Hotel-Information) West Yarmouth 9.4/10 Exceptional (101 reviews) "Clean, nice staff, good amenities, central location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Malbis £101 includes taxes & fees 7 Feb - 8 Feb [](https://www.expedia.co.uk/West-Yarmouth-Hotels-Tidewater-Inn.h480770.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) ![Exterior](https://images.trvl-media.com/lodging/41000000/40290000/40283500/40283414/e4387afe.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) ![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) ### Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK [](https://www.expedia.co.uk/Chatham-Hotels-Quaint-Chatham-Home-Wbeautiful-Backyard-Furnished-Multi-Level-Deck.h40283414.Hotel-Information) Chatham 9.6/10 Exceptional (102 reviews) "House was as advertised. Very clean and comfortable.we loved the fireplace and the large deck was great.we walked to Hardings beach in the morning.Highly recommend this vacation home" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda W. £314 includes taxes & fees 19 Jan - 20 Jan [](https://www.expedia.co.uk/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) ![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) ![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) ### Brayton Point Beach Bungalow in Somerset Massachusetts [](https://www.expedia.co.uk/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. £173 includes taxes & fees 22 Jan - 23 Jan [](https://www.expedia.co.uk/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/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) ![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) ### Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail [](https://www.expedia.co.uk/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. £401 includes taxes & fees 21 Jan - 22 Jan [](https://www.expedia.co.uk/Brewster-Hotels-Cheery-House-Wdeck.h72434954.Hotel-Information) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/77000000/76670000/76664200/76664195/ec7f5979.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/77000000/76670000/76664200/76664195/40c1b64d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76670000/76664200/76664195/6d5b6832.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76670000/76664200/76664195/7b4a3afe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Beach & Pond Getaway; Heart of Cape Cod [](https://www.expedia.co.uk/South-Yarmouth-Hotels-Homey-Central-Vacay-W-Game-Room-Near-Beach-And-Pond.h76664195.Hotel-Information) South Yarmouth 10/10 Exceptional (12 reviews) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin B. £406 includes taxes & fees 30 Jan - 31 Jan [](https://www.expedia.co.uk/South-Yarmouth-Hotels-Homey-Central-Vacay-W-Game-Room-Near-Beach-And-Pond.h76664195.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.co.uk/Hotel-Search?startDate=2026-01-31&endDate=2026-02-01®ionId=6047675&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Southeast Massachusetts Hotel Reviews ![Bayside Resort Hotel](https://images.trvl-media.com/lodging/1000000/900000/896700/896697/85f07916_y.jpg) ### Bayside Resort Hotel 10/10 Excellent "Yes really good everything sarissha the one clean room she did good job " [](https://expedia.co.uk/West-Yarmouth-Hotels-Bayside-Resort-Hotel.h896697.Hotel-Information) ![Hilton Garden Inn Plymouth](https://images.trvl-media.com/lodging/2000000/1450000/1449300/1449222/bbc0652b_y.jpg) ### Hilton Garden Inn Plymouth 10/10 Excellent "Staff was very friendly " [](https://expedia.co.uk/Plymouth-Hotels-Hilton-Garden-Inn-Plymouth.h1449222.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.co.uk/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.co.uk/Hyannis-Hotels-Cape-Codder-Resort-And-Spa.h12897.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 "We had a great time! The staff was very friendly , rooms smelled nice and clean, the beds were comfy- the kids loved the pool! Only flaw was children under 16 not allowed in hot tub but other than that we had a great stay! " [](https://expedia.co.uk/Plymouth-Hotels-John-Carver-Inn-Spa.h6589076.Hotel-Information) ![Falmouth Inn](https://images.trvl-media.com/lodging/1000000/900000/893200/893142/a26689a2_y.jpg) ### Falmouth Inn 10/10 Excellent "Room was clean. Staff was friendly " [](https://expedia.co.uk/Falmouth-Hotels-Falmouth-Inn.h893142.Hotel-Information) ![Chatham Bars Inn](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/w5700h3895x0y5-016d240d_y.jpg) ### Chatham Bars Inn 10/10 Excellent "Rooms were quaint, clean, and unique. Will definitely be staying again!!" [](https://expedia.co.uk/Chatham-Hotels-Chatham-Bars-Inn.h19139.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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