A marina with numerous sailboats docked at wooden piers.

Search Winery Hotels in Eastern Maryland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Eastern Maryland Winery Hotels

Tonight
10 Oct - 11 Oct
Tomorrow
11 Oct - 12 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

Our top choices for Eastern Maryland hotels with winery

A multi-story hotel with balconies, a beachside location, and various shops and restaurants.
A beach with umbrellas and people.
An outdoor seating area with tables and chairs, overlooking a beach.
A multi-story hotel with a pool area, including sun loungers and a smaller pool.

1. Park Place Hotel

Park Place Hotel
Downtown Ocean City
United States
valerie
£62
includes taxes & fees
2 Nov - 3 Nov
Park Place Hotel
A deck with two Adirondack chairs and a small table, overlooking a beach with the ocean and a clear sky.
A hotel room with a large bed, a desk, a chair, and a view of the city through large windows.
A modern hotel lobby with grey upholstered chairs, a round table, and a bar area.
A swimming pool with lounge chairs and umbrellas, surrounded by buildings and palm trees.

2. Hyatt Place Ocean City / Oceanfront

Hyatt Place Ocean City / Oceanfront
Downtown Ocean City
United States
Amy
£68
includes taxes & fees
2 Nov - 3 Nov
Hyatt Place Ocean City / Oceanfront
A large, historic house with a wrap-around porch and a gazebo, surrounded by lush vegetation and a body of water.
A river with a dock, a sailboat, and a motorboat. There are buildings and trees in the background.
A covered porch with wicker furniture, a small table, and a view of a green landscape and water.
A waterfront dock with a pier, a white building, and a clear sky.

3. The Whitehaven Hotel

The Whitehaven Hotel
Quantico
United States
Tracy
£112
includes taxes & fees
1 Nov - 2 Nov
The Whitehaven Hotel
A coastal hotel with multiple buildings, a beach, and a pier in the background.
A beachfront hotel with multiple balconies, a boardwalk, and a view of the ocean.
An indoor swimming pool with lounge chairs and a view of the outside balconies.
A hotel room with two beds, a desk, a chair, a TV, and a view of the ocean.

4. Courtyard Ocean City Oceanfront

Courtyard Ocean City Oceanfront
Downtown Ocean City
United States
Gonzalo
£71
includes taxes & fees
1 Nov - 2 Nov
Courtyard Ocean City Oceanfront
A balcony with two blue Adirondack chairs facing a beach with a white fence and a clear sky.
A modern hotel room with a bed, a sofa, a desk, and a chair.
A beach with numerous umbrellas and people.
The exterior of SeaLoft Oceanfront Hotel with a prominent sign and a balcony with white railings.

5. SeaLoft Oceanfront Hotel

SeaLoft Oceanfront Hotel
Midtown Ocean City
United States
Jessica
£60
includes taxes & fees
1 Nov - 2 Nov
SeaLoft Oceanfront Hotel
A large, multi-story Victorian-style house with a prominent tower and a wrap-around porch.
A grand staircase with ornate woodwork, a fireplace with a checkered floor, and a cozy seating area with a lamp.
A room with a wooden cabinet, two upholstered chairs, a radiator, and a stained glass window.
A dining room with a long table, white chairs, a chandelier, and wooden paneling.

6. Gillis Grier Bed & Breakfast

Gillis Grier Bed & Breakfast
Salisbury
United States
Devra
£141
includes taxes & fees
16 Oct - 17 Oct
Gillis Grier Bed & Breakfast
An indoor swimming pool with clear glass walls, lounge chairs, and a view of the outside.
A compact hotel room with a kitchenette, a dining area with a view, and a green armchair.
An outdoor patio with tables and chairs, blue umbrellas, and potted plants.
A modern hotel room with a large window, a flat-screen TV, a blue sofa, a yellow ottoman, and a green armchair.

7. Comfort Inn Gold Coast

Comfort Inn Gold Coast
North Ocean City
United States
Michele
£57
includes taxes & fees
1 Nov - 2 Nov
Comfort Inn Gold Coast
A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
A Comfort Inn & Suites hotel with a brick facade, arched entryway, and a well-maintained lawn.
A spacious dining area with multiple tables and chairs, a central island, and a kitchen in the background.

8. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Amy
£82
includes taxes & fees
8 Nov - 9 Nov
Comfort Inn & Suites Chestertown
A swimming pool with blue lounge chairs and striped umbrellas.
A hotel room with a large bed, a bathroom with a mosaic tile wall, a small table with two chairs, and a floor lamp.
A white beach ball with "Monte Carlo Hotel Group" and "Ocean City, MD" text.
A bar area with stone walls, metal chairs, and two TVs mounted on the wall.

9. Hotel Monte Carlo Ocean City

Hotel Monte Carlo Ocean City
Downtown Ocean City
United States
Jacob
£77
includes taxes & fees
15 Oct - 16 Oct
Hotel Monte Carlo Ocean City
A waterfront property with a prominent building featuring a red roof and a tower, surrounded by water and marshland.
A spacious lobby with wooden ceiling, comfortable seating, large windows, and a fireplace.
A cozy living room with a fireplace, a chessboard, and a tray with snacks and drinks.
A rocking chair on a wooden deck with a view of the ocean and a sunset.

10. Lighthouse Club Hotel

Lighthouse Club Hotel
Midtown Ocean City
United States
Corey
£165
includes taxes & fees
8 Nov - 9 Nov
Lighthouse Club Hotel
View all properties

Top Eastern Maryland Hotel Reviews

Explore a world of travel with Expedia