Title: TOP Winery Hotels in Southern Maryland, MD for 2025 | Expedia.co.uk [Southern Maryland Travel Guide](https://expedia.co.uk/Southern-Maryland.dx6057463)[Hotels in Southern Maryland](https://expedia.co.uk/Southern-Maryland-Hotels.d6057463.Travel-Guide-Hotels)[Holiday Rentals in Southern Maryland](https://expedia.co.uk/Southern-Maryland-Holiday-Rentals.d6057463.Travel-Guide-HolidayRentals)[Flights to Southern Maryland](https://expedia.co.uk/Cheap-Flights-To-Southern-Maryland.d6057463.Travel-Guide-Flights)[Southern Maryland Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Southern-Maryland.d6057463.Car-Hire-Guide)[Southern Maryland Holidays](https://expedia.co.uk/Southern-Maryland.d6057463.Holidays-City-Breaks) ![New home on the Chesapeake Bay! I live right next door to this fabulous lighthouse, which is fabulous! The lighthouse museum has limited hours, but the lighthouse keeper's house is now a vacation rental! People use the area for weddings, which sounds sweet.](https://images.trvl-media.com/place/6359190/72c34e0d-ce13-4f4d-ac16-fb3558228949.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Meg Faller # Search Winery Hotels in Southern Maryland - ![](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 Southern Maryland Winery Hotels Tonight [27 Nov - 28 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=6057463&startDate=2025-11-27&endDate=2025-11-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [28 Nov - 29 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=6057463&startDate=2025-11-28&endDate=2025-11-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [28 Nov - 30 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=6057463&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [5 Dec - 7 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=6057463&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Southern Maryland Winery Hotels ![Outdoor pool](https://images.trvl-media.com/lodging/72000000/71120000/71116900/71116837/aabd7b99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/72000000/71120000/71116900/71116837/10bef897.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71120000/71116900/71116837/a336c972.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71120000/71116900/71116837/488be20b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relaxing, peaceful house in Calvert County, Md close to beach towns and DC. Owings 10/10 Exceptional (48) "We love this place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joan K. £192 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Close-To-North-Chesapeake-Beach.h71116837.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/97000000/96640000/96637800/96637704/b3cbb2b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/97000000/96640000/96637800/96637704/36d81978.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/97000000/96640000/96637800/96637704/35851591.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96640000/96637800/96637704/d31a8fd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch. Benedict 9.2/10 Wonderful (7) "The owner was very nice " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) karen £231 includes taxes & fees 28 Nov - 29 Nov [](https://www.expedia.co.uk/Benedict-Hotels-Peaceful-Suite-On-The-Water-Osprey-Sunrise-Over-The-River-From-Your-Porch.h96637704.Hotel-Information) ![3 bedrooms, iron/ironing board, travel cot, free WiFi](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522263/9a42128d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522263/4429fbeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522263/287cc71d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522263/a1c3089f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space. Prince Frederick 9.6/10 Exceptional (4) "We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carrie K. £281 includes taxes & fees 1 Dec - 2 Dec [](https://www.expedia.co.uk/Prince-Frederick-Hotels-Kick-Back-And-Enjoy-The-Chesapeake-This-3-Bedroom.h113522263.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/110000000/109980000/109977800/109977749/w506h683x258y0-cd0997d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/110000000/109980000/109977800/109977749/w509h683x257y0-cf384e61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109980000/109977800/109977749/5cfce5c9_edited_5eeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109980000/109977800/109977749/w906h683x59y0-c873d7ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful Waterfront Apartment in the Heart of Solomons Island Solomons 9.0/10 Wonderful (14) "Nice little place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric S. £228 includes taxes & fees 4 Dec - 5 Dec [](https://www.expedia.co.uk/Solomons-Hotels-Waterfront-Solomons-Apartment.h109977749.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/104000000/103640000/103638100/103638094/624fee99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103640000/103638100/103638094/598c5e4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103640000/103638100/103638094/fcc30818.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103640000/103638100/103638094/9a1b795e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt! Prince Frederick 10/10 Exceptional (8) "Clean and easy " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert R. £271 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Prince-Frederick-Hotels-2-Blocks-From-Dares-Beach-On-The-Chesapeake-Bay-Beach-And-Boat-Access.h103638094.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/110000000/109980000/109977800/109977743/w917h683x60y0-ede3f4e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109980000/109977800/109977743/w904h683x60y0-20781af6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109980000/109977800/109977743/w907h683x58y0-48558967.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, desk, WiFi](https://images.trvl-media.com/lodging/110000000/109980000/109977800/109977743/ac3fa71f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 6-Bedroom Solomons Island Retreat • Walk to Waterfront & Shops Solomons 9.6/10 Exceptional (7) "Stayed for business, completed our project and enjoyed some local eating spots. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Justin J. £528 includes taxes & fees 4 Dec - 5 Dec [](https://www.expedia.co.uk/Solomons-Hotels-Roomy-6-Bedroom-Home-In-The-Heart-Of-Solomons.h109977743.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104110000/104104200/104104141/f1d9a8f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/105000000/104110000/104104200/104104141/78c5a13a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/105000000/104110000/104104200/104104141/08f9ea4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Games room](https://images.trvl-media.com/lodging/105000000/104110000/104104200/104104141/685c3115.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverfront Retreat-HotTubIDock|Fenced YardINear DC port tobacco 10/10 Exceptional (9) "Beautiful location for our family to stay to celebrate. It exceeded our expectations. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller £528 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Port-Tobacco-Hotels-Waterfront-River-Retreat-DockCanoeHotTubNear-DC.h104104141.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/62000000/61630000/61620200/61620102/8827d8be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/62000000/61630000/61620200/61620102/986120f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/62000000/61630000/61620200/61620102/be9b6a6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/62000000/61630000/61620200/61620102/352737c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Come relax yourself a while Mechanicsville £452 includes taxes & fees 28 Nov - 29 Nov [](https://www.expedia.co.uk/Mechanicsville-Hotels-Come-Relax-Yourself-A-While.h61620102.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/91000000/90260000/90258000/90257929/a1cbfbbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90260000/90258000/90257929/94de52a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/91000000/90260000/90258000/90257929/5efc662c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90260000/90258000/90257929/f374d762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Stay By MadlyGiving - At National Harbor National Harbor/Oxon Hill £725 includes taxes & fees 3 Dec - 4 Dec [](https://www.expedia.co.uk/Washington-Hotels-Private-Stay-By-MadlyGiving-At-National-Harbor.h90257929.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/42000000/41510000/41504700/41504609/25e69fb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed | In-room safe, blackout curtains, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/42000000/41510000/41504700/41504609/1e187bf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop bar](https://images.trvl-media.com/lodging/42000000/41510000/41504700/41504609/a9c246bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/42000000/41510000/41504700/41504609/0a84804c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Thompson Washington D.C., by Hyatt Navy Yard 9.2/10 Wonderful (1005) "Great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jose D. £96 includes taxes & fees 23 Dec - 24 Dec [](https://www.expedia.co.uk/Washington-Hotels-Thompson-Washington-DC.h41504609.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=2025-12-11&endDate=2025-12-12®ionId=6057463&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_FR-DE-MX-UK_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Save up to 40% on select hotels. 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[Car hire Hollywood](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Hollywood.d6060257.Car-Hire-Guide) - [Car hire La Plata](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-La-Plata.d10012.Car-Hire-Guide) - [Car hire Prince Frederick](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Prince-Frederick.d500577.Car-Hire-Guide) - [Car hire Waldorf](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Waldorf.d6057464.Car-Hire-Guide) - [Sixt Rental Cars in Broomes Island](https://www.expedia.co.uk/Sixt-Car-Rentals-In-Broomes-Island.d3000440453-c35.Car-Rental-Guide-Suppliers) - [Car hire in Thrifty Car Rental 8620 Panair St](https://www.expedia.co.uk/Thrifty-Car-Rental-at-8620-Panair-St-Houston-Texas-USA.v83959.Car-Rental-Guide-Location) - [Mechanicsville Holiday Rentals](https://www.expedia.co.uk/Mechanicsville-Holiday-Rentals.d6278560.Travel-Guide-HolidayRentals) - [Book Winery Hotels in Southern Maryland on Expedia.com](https://www.expedia.com/Southern-Maryland-Hotels-Winery-Hotel.0-0-d6057463-tWineryHotel.Travel-Guide-Filter-Hotels)