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) ![Southeast Massachusetts featuring a river or creek, fishing and autumn colours](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__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 [4 Mar - 5 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=6047675&startDate=2026-03-04&endDate=2026-03-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [5 Mar - 6 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=6047675&startDate=2026-03-05&endDate=2026-03-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [6 Mar - 8 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=6047675&startDate=2026-03-06&endDate=2026-03-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [13 Mar - 15 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=6047675&startDate=2026-03-13&endDate=2026-03-15&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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/e74c9a7c.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) ![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 (638 reviews) "Yes, lovely place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela £108 includes taxes & fees 5 Mar - 6 Mar [](https://www.expedia.co.uk/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.Hotel-Information) ![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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/9100/9001/906376aa.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) ### 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 (1,000 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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/15000000/14850000/14845000/14844940/3d82ccd1.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 (298 reviews) "Beat B&B i have ever stayed at! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Philip £111 includes taxes & fees 5 Mar - 6 Mar [](https://www.expedia.co.uk/Falmouth-Hotels-Frederick-William-House.h14844940.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) ![TV](https://images.trvl-media.com/lodging/3000000/2800000/2796200/2796134/26470c3b.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) ![Exterior](https://images.trvl-media.com/lodging/3000000/2800000/2796200/2796134/34cdb618.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 (162 reviews) "It was a wonderful stay. Highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hye-Won £108 includes taxes & fees 5 Mar - 6 Mar [](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) ![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.co.uk/West-Yarmouth-Hotels-Tidewater-Inn.h480770.Hotel-Information) West Yarmouth 9.2/10 Wonderful (115 reviews) "Clean, nice staff, good amenities, central location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Malbis £104 includes taxes & fees 5 Mar - 6 Mar [](https://www.expedia.co.uk/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 | 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) ![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 £175 includes taxes & fees 5 Mar - 6 Mar [](https://www.expedia.co.uk/Yarmouth-Port-Hotels-The-Village-Inn-Cape-Cod.h12426891.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/114000000/113540000/113530600/113530554/4d19d374.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113540000/113530600/113530554/dff6c967.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/114000000/113540000/113530600/113530554/b5aa0c51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113540000/113530600/113530554/c89c3683.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Big Sandy Beachcomber [](https://www.expedia.co.uk/Plymouth-Hotels-Spacious-4-Bed-Fenced-In-Yard-15-Min-To-Downtown-Plymouth.h113530554.Hotel-Information) Ponds of Plymouth 9.6/10 Exceptional (14 reviews) "Our stay was perfect! The house was clean and the host very responsive throughout! Would definitely stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ben L. [](https://www.expedia.co.uk/Plymouth-Hotels-Spacious-4-Bed-Fenced-In-Yard-15-Min-To-Downtown-Plymouth.h113530554.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) ![Terrace/patio](https://images.trvl-media.com/lodging/41000000/40290000/40283500/40283414/203d6415.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.co.uk/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. £348 includes taxes & fees 5 Mar - 6 Mar [](https://www.expedia.co.uk/Chatham-Hotels-Quaint-Chatham-Home-Wbeautiful-Backyard-Furnished-Multi-Level-Deck.h40283414.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) ![Exterior](https://images.trvl-media.com/lodging/73000000/72440000/72435000/72434954/a7d1d86a.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. £431 includes taxes & fees 5 Mar - 6 Mar [](https://www.expedia.co.uk/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) ![Living area](https://images.trvl-media.com/lodging/89000000/88190000/88181300/88181254/05cf438c.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) ### Cozy three-bedroom home close to Boston w/ plenty of parking [](https://www.expedia.co.uk/Boston-Hotels-Cozy-Three-Bedroom-Home-Close-To-Boston-W-Plenty-Of-Parking.h88181254.Hotel-Information) North Braintree 10/10 Exceptional (45 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. £335 includes taxes & fees 8 Mar - 9 Mar [](https://www.expedia.co.uk/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.co.uk/Hotel-Search?startDate=2026-03-18&endDate=2026-03-19®ionId=6047675&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-uk-fr-de.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Holiday Sale Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save. [Book now](https://expedia.co.uk/cheap-deals?rfrr=AFFINITY_SPRING_PROMO_6047675) ## Top Southeast Massachusetts Hotel Reviews ![Margaritaville Resort Cape Cod](https://images.trvl-media.com/lodging/1000000/20000/12900/12897/b57e0b1f_y.jpg) ### Margaritaville Resort Cape Cod 10/10 Excellent "Staff are amazing, place is beautiful, clean and all around wonderful place " [](https://expedia.co.uk/Hyannis-Hotels-Cape-Codder-Resort-And-Spa.h12897.Hotel-Information) ![Hampton Inn & Suites Plymouth](https://images.trvl-media.com/lodging/2000000/1540000/1536000/1535980/8d27b6f3_y.jpg) ### Hampton Inn & Suites Plymouth 6/10 Okay "The check in was almost an hour late and the woman at the desk was very cold about the whole situation" [](https://expedia.co.uk/Plymouth-Hotels-Hampton-Inn-Suites-Plymouth.h1535980.Hotel-Information) ![John Carver Inn & Spa](https://images.trvl-media.com/lodging/7000000/6590000/6589100/6589076/4f9cc923_y.jpg) ### John Carver Inn & Spa 4/10 Poor "Kids was running around and knocking peoples door my kids couldn’t sleep I thought was a family hotel…" [](https://expedia.co.uk/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 "The room was very clean; I will say I do not like staying overlooking the pool the chlorine smell is very strong. Check in and out was great, easy - fast. " [](https://expedia.co.uk/Plymouth-Hotels-Hotel-1620-Plymouth-Harbor.h9001.Hotel-Information) ![Summercamp](https://images.trvl-media.com/lodging/11000000/10060000/10058600/10058501/c4bc64d6_y.jpg) ### Summercamp 10/10 Excellent "Lovely stay and the staff was friendly and helpful. Excellent location. 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