A heron standing in a golden-hued wetland with a bird flying in the background.

Search Winery Hotels in Southern Maryland

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Check availability on Southern Maryland Winery Hotels

Tonight
13 Oct - 14 Oct
Tomorrow
14 Oct - 15 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Southern Maryland hotels with winery

A room with a white door, a wooden coat rack with robes, a lamp, and a bottle on a side table.
Front of property
A driveway leading to a parked convertible car with an American flag on the side.
A person holding a shark tooth in a room with a staircase, a red chair, and patterned carpet.

1. Historic 1825 Chesapeake Farm Stay

Historic 1825 Chesapeake Farm Stay
St. Leonard
United States
Theresa
£104
includes taxes & fees
12 Nov - 13 Nov
Historic 1825 Chesapeake Farm Stay
A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.
A pebbled beach with a wooden pier extending into calm water, surrounded by trees and grassy areas.
A bedroom with a bed, nightstands, a ceiling fan, and two windows with blinds.
A wooden pier extending into calm water with a sunset in the background.

2. Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
United States
ed r.
£203
includes taxes & fees
14 Oct - 15 Oct
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
A lakeside view with chairs and a table, a rainbow, and trees.
A sandy beach with footprints, surrounded by greenery and a calm body of water.
A compact kitchen with a white countertop, a stainless steel refrigerator, and a dining area with a table and chairs.
A compact kitchen with white cabinets, a stainless steel oven, a black stove, and a sink.

3. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
United States
George
£272
includes taxes & fees
14 Oct - 15 Oct
Bright and airy waterfront getaway
A two-story house with a deck and a staircase leading to the upper floor.
A bedroom with a large bed, a nightstand with a lamp, a dresser, and a door leading to another room.
A dining area with a round table, four wooden chairs, and two paintings on the wall.
A sign for Stratford on the Potomac with a brick wall and greenery around.

4. MOUNT VERNON RETREAT 🌸

MOUNT VERNON RETREAT 🌸
Alexandria
United States
Tiffany Z.
£220
includes taxes & fees
20 Oct - 21 Oct
MOUNT VERNON RETREAT 🌸
A spacious living room with a green sofa, glass coffee tables, and a fireplace. A staircase with a railing leads to an upper level.
A spacious living room with a green sofa, a fireplace, a staircase leading to a balcony, and a large window with a view of the outdoors.
A backyard with a fire pit, Adirondack chairs, and a wooden deck.
A modern kitchen with white cabinetry, a central island, and built-in ovens.

5. Riverfront Retreat-HotTubIDock|Fenced YardINear DC

Riverfront Retreat-HotTubIDock|Fenced YardINear DC
port tobacco
United States
Jeff and Nancy B.
£417
includes taxes & fees
14 Oct - 15 Oct
Riverfront Retreat-HotTubIDock|Fenced YardINear DC
A kitchen with white cabinets, a stainless steel refrigerator, a checkered island, and a two-tiered serving tray.
A living room with a fireplace, a black leather sofa, a round coffee table, and two white armchairs.
A living room with a fireplace, a dining area with two chairs, a kitchen with a marble countertop, and a large mirror.
A bedroom with a tufted headboard bed, a bench, a patterned rug, and a ceiling fan.

6. 43 acre private retreat for the whole family within minutes of DC

43 acre private retreat for the whole family within minutes of DC
Nanjemoy
United States
Khanh N.
£1,058
includes taxes & fees
2 Nov - 3 Nov
43 acre private retreat for the whole family within minutes of DC
An indoor restaurant with wooden tables and chairs, hanging plants, and a black and white patterned floor.
A modern hotel lobby with a reception desk, a large red abstract mural, a herringbone wood floor, a seating area with a sofa and chairs, and a bar with a high counter.
A hotel hallway with wooden doors, a patterned carpet, and recessed lighting.
A modern bedroom with a large bed, a red chair, and a city view through large windows.

7. The Rose Gaming Resort

The Rose Gaming Resort
Dumfries
United States
Catherine
£100
includes taxes & fees
8 Nov - 9 Nov
The Rose Gaming Resort
A large, two-story barn-style building with a covered front porch and a garage.
A large, two-story white house with a porch and multiple windows.
A rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.
A bedroom with a large bed, a bench, a dresser, and two windows with curtains.

8. Kent Island Resort

Kent Island Resort
Stevensville
United States
Bethany
£127
includes taxes & fees
28 Oct - 29 Oct
Kent Island Resort
An outdoor patio area with seating arrangements, a fire pit, and a covered walkway.
An indoor swimming pool with clear water, surrounded by lounge chairs and a view of the outdoors.
A modern lobby with a patterned carpet, blue chairs, a wooden coffee table, and a decorative wall with a spherical ornament.
Exterior

9. Courtyard Stafford Quantico

Courtyard Stafford Quantico
Stafford
United States
James
£100
includes taxes & fees
25 Oct - 26 Oct
Courtyard Stafford Quantico
A modern building with a brick facade, large windows, and a sign reading "221 THOMPSON WASHINGTON DC".
A corner room with a view of a river, a desk, a chair, and a floor lamp.
A modern bar area with a central island, bar stools, and a seating area with sofas and chairs.
A spacious lobby with a central reception desk, seating area, and a large bookshelf.

10. Thompson Washington D.C., by Hyatt

Thompson Washington D.C., by Hyatt
Navy Yard
United States
Noreen
£134
includes taxes & fees
1 Nov - 2 Nov
Thompson Washington D.C., by Hyatt
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Top Southern Maryland Hotel Reviews

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