A marina with numerous boats docked at wooden piers under a clear sky.

Find Winery Hotels in Eastern Shore, MD

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Check availability on Eastern Shore Winery Hotels

Tonight
Oct 25 - Oct 26
Tomorrow
Oct 26 - Oct 27
Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8

Our top choices for Eastern Shore hotels with winery

A hotel lobby with a fireplace, seating area, and a television.
A hotel room with two beds, a desk, a flat-screen TV, and a window with curtains.
A hotel room with a bed, a sofa, a dining table, and a small round table.
A spacious dining area with multiple tables and chairs, a central island, and a kitchen in the background.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Roberta
NT$3,199
NT$3,551 total
includes taxes & fees
Nov 15 - Nov 16
Comfort Inn & Suites Chestertown
A deck with two Adirondack chairs and a small table, overlooking a beach with the ocean and a clear sky.
A swimming pool with lounge chairs and umbrellas, surrounded by buildings and palm trees.
A beach with a wooden boardwalk, umbrellas, and people.
A modern hotel lobby with grey upholstered chairs, a round table, and a bar area.

2. Hyatt Place Ocean City / Oceanfront

Hyatt Place Ocean City / Oceanfront
Downtown Ocean City
United States
Larry
NT$2,608
NT$2,921 total
includes taxes & fees
Nov 2 - Nov 3
Hyatt Place Ocean City / Oceanfront
A multi-story hotel with balconies, a beachside location, and various shops and restaurants.
A vibrant hotel lobby with a blue sofa, colorful artwork, a surfboard, and a modern chandelier.
An outdoor seating area with tables and chairs, overlooking a beach.
A beach with umbrellas and people.

3. Park Place Hotel

Park Place Hotel
Downtown Ocean City
United States
kevin
NT$1,766
NT$2,718 total
includes taxes & fees
Oct 26 - Oct 27
Park Place Hotel
An indoor swimming pool with clear glass walls, lounge chairs, and a view of the outside.
A modern hotel room with a large window, a flat-screen TV, a blue sofa, a yellow ottoman, and a green armchair.
An outdoor patio with tables and chairs, blue umbrellas, and potted plants.
A compact hotel room with a kitchenette, a dining area with a view, and a green armchair.

4. Comfort Inn Gold Coast

Comfort Inn Gold Coast
North Ocean City
United States
michael
NT$2,106
NT$2,358 total
includes taxes & fees
Nov 25 - Nov 26
Comfort Inn Gold Coast
Room
A hotel room with two beds, a desk, a chair, a TV, and a view of the ocean.
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.

5. Courtyard Ocean City Oceanfront

Courtyard Ocean City Oceanfront
Downtown Ocean City
United States
Ryan
NT$2,841
NT$3,181 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard Ocean City Oceanfront
A large, two-story barn-style building with a covered front porch and a garage.
A rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.
A large, two-story white house with a porch and multiple windows.
A bedroom with a large bed, a bench, a dresser, and two windows with curtains.

6. Kent Island Resort

Kent Island Resort
Stevensville
United States
Bethany
NT$3,989
NT$5,506 total
includes taxes & fees
Nov 16 - Nov 17
Kent Island Resort
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.
A modern hotel lobby with a large wall sign reading "SeaLoft Oceanfront Hotel," wicker furniture, a leather sofa, and a view of the street through a large window.

7. SeaLoft Oceanfront Hotel

SeaLoft Oceanfront Hotel
Midtown Ocean City
United States
Jessica
NT$2,575
NT$2,885 total
includes taxes & fees
Oct 29 - Oct 30
SeaLoft Oceanfront Hotel
A hotel room with two beds, a desk, a chair, and a wall-mounted TV.
A reception area with a modern design, featuring a reception desk, a mounted television, a clock, and a large painting on the wall.
A modern hotel with a prominent 'Wingate by Wyndham' sign, a covered entrance, and a flag.
An indoor swimming pool with clear glass walls, blue chairs around the pool, and a tiled floor.

8. Wingate by Wyndham North East

Wingate by Wyndham North East
North East
United States
Bonnie
NT$2,670
NT$2,990 total
includes taxes & fees
Nov 15 - Nov 16
Wingate by Wyndham North East
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 rocking chair on a wooden deck with a view of the ocean and a sunset.
A restaurant with large windows offering a view of the sea. Tables are set with white tablecloths and wooden chairs.

9. Lighthouse Club Hotel

Lighthouse Club Hotel
Midtown Ocean City
United States
Corey
NT$6,357
NT$7,120 total
includes taxes & fees
Nov 8 - Nov 9
Lighthouse Club Hotel
A modern living room with a large window overlooking the sea, a sofa, a fireplace, and a flat-screen TV mounted on the wall.
A bedroom with a bed, a sofa, a TV, a fireplace, and a view of the sea.
A modern living room with a large sofa, a coffee table, and a TV. There are large windows with a view of the water and a balcony.
A modern bathroom with a large bathtub, a white sink, and a view of the sea through large windows.

10. The Edge at Fager's Island

The Edge at Fager's Island
Midtown Ocean City
United States
Liana
NT$8,900
NT$9,968 total
includes taxes & fees
Nov 1 - Nov 2
The Edge at Fager's Island
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Top Eastern Shore Hotel Reviews

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