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 ![](https://images.trvl-media.com/place/6359190/72c34e0d-ce13-4f4d-ac16-fb3558228949.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Jan 31 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6057463&startDate=2026-01-31&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 1 - Feb 2](https://www.expedia.ca/Hotel-Search?regionId=6057463&startDate=2026-02-01&endDate=2026-02-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6057463&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6057463&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Southern Maryland hotels with winery ![Reception](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/f2cc9e28.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) ![Aerial view](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a0732bf1.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) ### Kent Island Resort [](https://www.expedia.ca/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information) Stevensville 9.2/10 Wonderful (132 reviews) "Beautiful hotel, nice staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim CA $170 CA $236 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information) ![Indoor pool, open 10:00 AM to midnight, sun loungers](https://images.trvl-media.com/lodging/2000000/1600000/1593000/1592959/07d179f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Laptop workspace, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/2000000/1600000/1593000/1592959/90c6c502.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1600000/1593000/1592959/ae768bbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/2000000/1600000/1593000/1592959/b0f9e974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Near Quantico Main Gate North [](https://www.expedia.ca/Dumfries-Hotels-Comfort-Inn-Near-Quantico-Main-Gate-North.h1592959.Hotel-Information) Dumfries 8.6/10 Excellent (849 reviews) "Clean room, friendly staff and nice overall accommodation" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $108 CA $123 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Dumfries-Hotels-Comfort-Inn-Near-Quantico-Main-Gate-North.h1592959.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/26700/26629/f0e8c5ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/26700/26629/e04548f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Double Beds](https://images.trvl-media.com/lodging/1000000/30000/26700/26629/18ef1595.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/26700/26629/5e121d6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ramada by Wyndham Triangle/Quantico [](https://www.expedia.ca/Triangle-Hotels-Ramada-By-Wyndham-TriangleQuantico.h26629.Hotel-Information) Triangle 7.6/10 Good (1,000 reviews) "The hotel was very clean and the staff were friendly." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth CA $102 CA $117 total includes taxes & fees Feb 7 - Feb 8 [](https://www.expedia.ca/Triangle-Hotels-Ramada-By-Wyndham-TriangleQuantico.h26629.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96640000/96637800/96637704/df7451da.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) ![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) ![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) ### 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 reviews) "The owner was very nice " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) karen CA $245 CA $409 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/Benedict-Hotels-Peaceful-Suite-On-The-Water-Osprey-Sunrise-Over-The-River-From-Your-Porch.h96637704.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/35000000/34150000/34146400/34146318/w1124h750x106y0-5491995a.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) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34150000/34146400/34146318/108a2b49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/35000000/34150000/34146400/34146318/71a8699e.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 (129 reviews) "The perfect place to stay if youre going to Mount Vernon. Nice neighborhood. Responsive host. Clean and comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gina E. CA $178 CA $341 total includes taxes & fees Feb 12 - Feb 13 [](https://www.expedia.ca/Alexandria-Hotels-MOUNT-VERNON-RETREAT.h34146318.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/104000000/103640000/103638100/103638094/5aeb926e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103640000/103638100/103638094/f8f86577.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103640000/103638100/103638094/dd4e694d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103640000/103638100/103638094/7d735d64.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 reviews) "Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Olivia M. CA $272 CA $534 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/Prince-Frederick-Hotels-2-Blocks-From-Dares-Beach-On-The-Chesapeake-Bay-Beach-And-Boat-Access.h103638094.Hotel-Information) ![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) ![Interior](https://images.trvl-media.com/lodging/62000000/61630000/61620200/61620102/12b83ca0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/62000000/61630000/61620200/61620102/5016ee1b.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 $337 CA $802 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/Mechanicsville-Hotels-Come-Relax-Yourself-A-While.h61620102.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/aabb28e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/9ee94703.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/180dd9f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/fa54a5ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Candlewood Suites Annapolis by IHG [](https://www.expedia.ca/Annapolis-Hotels-Homestyle-Suites.h1160798.Hotel-Information) Annapolis 8.8/10 Excellent (203 reviews) "Hotel was clean staff was friendly" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim CA $114 CA $130 total includes taxes & fees Feb 5 - Feb 6 [](https://www.expedia.ca/Annapolis-Hotels-Homestyle-Suites.h1160798.Hotel-Information) ![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83510000/83500500/83500464/w906h683x59y0-6a81f3a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83510000/83500500/83500464/w905h683x60y0-4547a7ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/84000000/83510000/83500500/83500464/w536h683x248y0-22765b2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/84000000/83510000/83500500/83500464/w908h683x58y0-1d4078ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly updated 3 bedroom cottage with Solo Stove fire pit [](https://www.expedia.ca/Reedville-Hotels-Bayberry-Newly-Updated-3-Bedroom-Cottage.h83500464.Hotel-Information) Reedville 9.6/10 Exceptional (19 reviews) "Great place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Myranda R. CA $120 CA $327 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/Reedville-Hotels-Bayberry-Newly-Updated-3-Bedroom-Cottage.h83500464.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/110000000/109200000/109194100/109194034/8436c5d6_edited_0c5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109200000/109194100/109194034/a7b25b95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/110000000/109200000/109194100/109194034/w1080h1440x0y450-83f303b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/110000000/109200000/109194100/109194034/w1080h1440x0y450-ba4ff309.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville [](https://www.expedia.ca/Reedville-Hotels-Charming-3-Bedroom-House-With-WiFi.h109194034.Hotel-Information) Reedville 7.8/10 Good (8 reviews) "Nice place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Luis A. CA $136 CA $289 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/Reedville-Hotels-Charming-3-Bedroom-House-With-WiFi.h109194034.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=2026-02-15&endDate=2026-02-16®ionId=6057463&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Southern Maryland Hotel Reviews ![Solomons Inn Resort & Marina](https://images.trvl-media.com/lodging/1000000/30000/24900/24812/d9855215_y.jpg) ### Solomons Inn Resort & Marina 10/10 Excellent "Everything was great just need better outlets and b8gger fridge " [](https://expedia.ca/Solomons-Hotels-Solomons-Inn-Resort-Marina.h24812.Hotel-Information) ## 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) - 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