Title: Book the Best Southern Maryland WINERY Hotels in 2026 | 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) ![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 # Find Winery Hotels in Southern Maryland, MD from CA $125 - ![](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 [Dec 23 - Dec 24](https://www.expedia.ca/Hotel-Search?regionId=6057463&startDate=2025-12-23&endDate=2025-12-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 24 - Dec 25](https://www.expedia.ca/Hotel-Search?regionId=6057463&startDate=2025-12-24&endDate=2025-12-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6057463&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6057463&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Southern Maryland hotels with winery ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34150000/34146400/34146318/25950c8b.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) ![TV](https://images.trvl-media.com/lodging/35000000/34150000/34146400/34146318/a2530b2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34150000/34146400/34146318/40d1bf0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### MOUNT VERNON RETREAT 🌸 [](https://www.expedia.ca/Alexandria-Hotels-MOUNT-VERNON-RETREAT.h34146318.Hotel-Information) Alexandria 9.8/10 Exceptional (128) "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" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carolyn B. CA $154 CA $306 total includes taxes & fees Dec 31 - Jan 1, 2026 [](https://www.expedia.ca/Alexandria-Hotels-MOUNT-VERNON-RETREAT.h34146318.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/72000000/71120000/71116900/71116837/aabd7b99.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) ![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) ### Relaxing, peaceful house in Calvert County, Md close to beach towns and DC. [](https://www.expedia.ca/Close-To-North-Chesapeake-Beach.h71116837.Hotel-Information) Owings 10/10 Exceptional (48) "We love this place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joan K. CA $188 CA $390 total includes taxes & fees Dec 26 - Dec 27 [](https://www.expedia.ca/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) ![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) ![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. [](https://www.expedia.ca/Benedict-Hotels-Peaceful-Suite-On-The-Water-Osprey-Sunrise-Over-The-River-From-Your-Porch.h96637704.Hotel-Information) Benedict 9.0/10 Wonderful (8) "The owner was very nice " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) karen CA $246 CA $410 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Benedict-Hotels-Peaceful-Suite-On-The-Water-Osprey-Sunrise-Over-The-River-From-Your-Porch.h96637704.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) ![Beach nearby](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522263/4429fbeb.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) ![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. [](https://www.expedia.ca/Prince-Frederick-Hotels-Kick-Back-And-Enjoy-The-Chesapeake-This-3-Bedroom.h113522263.Hotel-Information) Prince Frederick 9.6/10 Exceptional (5) "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. CA $274 CA $537 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Prince-Frederick-Hotels-Kick-Back-And-Enjoy-The-Chesapeake-This-3-Bedroom.h113522263.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) ![Outdoor dining](https://images.trvl-media.com/lodging/104000000/103640000/103638100/103638094/7a849270.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt! [](https://www.expedia.ca/Prince-Frederick-Hotels-2-Blocks-From-Dares-Beach-On-The-Chesapeake-Bay-Beach-And-Boat-Access.h103638094.Hotel-Information) Prince Frederick 10/10 Exceptional (8) "Everything was amazing. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lorie S. CA $297 CA $564 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Prince-Frederick-Hotels-2-Blocks-From-Dares-Beach-On-The-Chesapeake-Bay-Beach-And-Boat-Access.h103638094.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22130000/22121200/22121103/1445eb3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/23000000/22130000/22121200/22121103/74187b21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/23000000/22130000/22121200/22121103/79d27909.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/23000000/22130000/22121200/22121103/61116c9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Call to reserve last minute stay! Hideaway in Hays Beach: 1 Minute Walk to Sand [](https://www.expedia.ca/Scotland-Hotels-Enjoy-The-Hideaway-In-Hays-Beach-On-Chesapeake-Bay-With-Internet-301-250-8384.h22121103.Hotel-Information) Point Lookout 10/10 Exceptional (125) "My family loved the fishing and crabbing. There were so many tools and toys available. Would love to make this a birthday and family tradition! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hannah A. CA $433 CA $848 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Scotland-Hotels-Enjoy-The-Hideaway-In-Hays-Beach-On-Chesapeake-Bay-With-Internet-301-250-8384.h22121103.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) ![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) ![Interior](https://images.trvl-media.com/lodging/62000000/61630000/61620200/61620102/be9b6a6f.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) ### Come relax yourself a while [](https://www.expedia.ca/Mechanicsville-Hotels-Come-Relax-Yourself-A-While.h61620102.Hotel-Information) Mechanicsville CA $339 CA $803 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Mechanicsville-Hotels-Come-Relax-Yourself-A-While.h61620102.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/69000000/68700000/68691100/68691073/4c02b7bd.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) ### Holiday Inn Express Washington DC Downtown by IHG [](https://www.expedia.ca/Washington-Hotels-Holiday-Inn-Express-Washington-DC-Downtown.h68691073.Hotel-Information) Downtown Washington D.C. 8.2/10 Very good (2082) "our stay was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $108 CA $125 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Washington-Hotels-Holiday-Inn-Express-Washington-DC-Downtown.h68691073.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/5b1966a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Single Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a98cfc15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a0732bf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Single Room, Balcony | Terrace/patio](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/2f6490c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kent Island Resort [](https://www.expedia.ca/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information) Stevensville 9.2/10 Wonderful (129) "Beautiful and peaceful property!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jerry CA $164 CA $230 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/6000000/5420000/5415000/5414912/c4ba7d5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/6000000/5420000/5415000/5414912/5aa1cc94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/6000000/5420000/5415000/5414912/43bb97d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/6000000/5420000/5415000/5414912/150446a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Quantico Stafford [](https://www.expedia.ca/Stafford-Hotels-Fairfield-Inn-Suites-By-Marriott-Quantico-Stafford.h5414912.Hotel-Information) Stafford 9.2/10 Wonderful (578) "Had a short stay, the staff was very friendly and helpful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kaitlyn CA $149 CA $173 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Stafford-Hotels-Fairfield-Inn-Suites-By-Marriott-Quantico-Stafford.h5414912.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=2026-01-07&endDate=2026-01-08®ionId=6057463&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Southern Maryland Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [Aquasco Hotels ](https://www.expedia.ca/Aquasco-Hotels.d3000347804.Travel-Guide-Hotels) - [Honeymoon Resorts and in Baltimore ](https://www.expedia.ca/Baltimore-Hotels-Honeymoon-Hotels.0-0-d178235-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Lazy River in Baltimore ](https://www.expedia.ca/Baltimore-Hotels-Hotels-With-A-Lazy-River.0-0-d178235-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Benedict ](https://www.expedia.ca/Benedict-Hotels-Cheap-Hotels.0-0-d3000347809-tCheapHotels.Travel-Guide-Filter-Hotels) - [Benedict Hotels ](https://www.expedia.ca/Benedict-Hotels.d3000347809.Travel-Guide-Hotels) - [Broomes Island Hotels ](https://www.expedia.ca/Broomes-Island-Hotels.d3000440453.Travel-Guide-Hotels) - 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