Title: Book the Best Southern Maryland WINERY Hotels in 2025 | Expedia.ca [Southern Maryland Travel Guide](https://expedia.ca/Southern-Maryland.dx6057463)[Hotels in Southern Maryland](https://expedia.ca/Southern-Maryland-Hotels.d6057463.Travel-Guide-Hotels)[Vacation Rentals in Southern Maryland](https://expedia.ca/Southern-Maryland-Vacation-Rentals.d6057463.Travel-Guide-VacationRentals)[Flights to Southern Maryland](https://expedia.ca/Cheap-Flights-To-Southern-Maryland.d6057463.Travel-Guide-Flights)[Southern Maryland Car Rentals](https://expedia.ca/Car-Rentals-In-Southern-Maryland.d6057463.Car-Rental-Guide)[Southern Maryland Vacation Packages](https://expedia.ca/Southern-Maryland.d6057463.Destination-Travel-Guides) ![George Washington\'s Mount Vernon showing flowers](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/135000/135140-Alexandria.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Southern Maryland, MD ![](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 Southern Maryland Winery Hotels Tonight [Oct 11 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6057463&startDate=2025-10-11&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=6057463&startDate=2025-10-12&endDate=2025-10-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6057463&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6057463&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Southern Maryland Winery Hotels ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34150000/34146400/34146318/25950c8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/35000000/34150000/34146400/34146318/a2530b2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34150000/34146400/34146318/w1124h750x106y0-5491995a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34150000/34146400/34146318/3f16e479.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### MOUNT VERNON RETREAT 🌸 Alexandria 9.8/10 Exceptional (125) "We had a great time. The property was clean and peaceful. It was far enough away from things to be quiet and relaxing but close enough to get to everything we needed to in a good amount of time" CA $154 CA $313 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Alexandria-Hotels-MOUNT-VERNON-RETREAT.h34146318.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) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/97000000/96640000/96637800/96637704/89e18a15.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) ![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 9.6/10 Exceptional (5) "Just the perfect place I needed for a personal retreat. It is quiet, peaceful and serene. I would definitely visit again. " CA $252 CA $419 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Benedict-Hotels-Peaceful-Suite-On-The-Water-Osprey-Sunrise-Over-The-River-From-Your-Porch.h96637704.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) ![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) ![Marina](https://images.trvl-media.com/lodging/110000000/109980000/109977800/109977749/w509h683x257y0-cf384e61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/110000000/109980000/109977800/109977749/c5bfacab_edited_b796.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Solomons Apartment Solomons 9.2/10 Wonderful (12) "Very clean, awesome location and amazing hosts!! " CA $189 CA $377 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/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) ![Exterior](https://images.trvl-media.com/lodging/104000000/103640000/103638100/103638094/9a1b795e.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) ![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) ### 2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt! Prince Frederick 10/10 Exceptional (6) "Clean and easy " CA $284 CA $549 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/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) ![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) ![Smart TV](https://images.trvl-media.com/lodging/110000000/109980000/109977800/109977743/w906h683x59y0-1b4c468d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Roomy 6 bedroom home in the heart of Solomons, MD Solomons 9.2/10 Wonderful (5) "Stayed for business, completed our project and enjoyed some local eating spots. " CA $404 CA $804 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Solomons-Hotels-Roomy-6-Bedroom-Home-In-The-Heart-Of-Solomons.h109977743.Hotel-Information) ![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522263/9a42128d.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) ![Beach nearby](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522263/4429fbeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522263/9ff5ea83.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 9.4/10 Exceptional (3) "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. " CA $317 CA $589 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Prince-Frederick-Hotels-Kick-Back-And-Enjoy-The-Chesapeake-This-3-Bedroom.h113522263.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) ![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) ![TV, stereo](https://images.trvl-media.com/lodging/62000000/61630000/61620200/61620102/376bd336.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Come relax yourself a while Mechanicsville CA $347 CA $829 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Mechanicsville-Hotels-Come-Relax-Yourself-A-While.h61620102.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/105000000/104110000/104104200/104104141/78c5a13a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/105000000/104110000/104104200/104104141/685c3115.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront River Retreat-Dock|Canoe|HotTub|Near DC port tobacco 10/10 Exceptional (9) "Beautiful location for our family to stay to celebrate. It exceeded our expectations. " CA $422 CA $907 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Port-Tobacco-Hotels-Waterfront-River-Retreat-DockCanoeHotTubNear-DC.h104104141.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) ![3 bedrooms, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/91000000/90260000/90258000/90257929/76262780.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) ### Private Stay By MadlyGiving - At National Harbor National Harbor/Oxon Hill CA $1,159 CA $1,346 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Washington-Hotels-Private-Stay-By-MadlyGiving-At-National-Harbor.h90257929.Hotel-Information) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/69000000/68700000/68691100/68691073/3afc16a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/69000000/68700000/68691100/68691073/a9a13bc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/69000000/68700000/68691100/68691073/aa301b84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/69000000/68700000/68691100/68691073/5b423cc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Washington DC Downtown by IHG Downtown Washington D.C. 8.2/10 Very good (1964) "Location is great!" CA $167 CA $194 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Washington-Hotels-Holiday-Inn-Express-Washington-DC-Downtown.h68691073.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. 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