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
Sep 23 - Sep 24
Tomorrow
Sep 24 - Sep 25
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for Eastern Shore hotels with winery

A modern dining area with a central island, multiple tables, and chairs. There are signs for 'RISP' and 'SILVER' on the wall, and an 'EXIT' sign above a door.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
A hotel reception area with a modern design, featuring a reception desk, a seating area, and a hallway leading to other rooms.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Amy
NT$3,401
NT$3,775 total
includes taxes & fees
Oct 14 - Oct 15
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 modern hotel lobby with grey upholstered chairs, a round table, and a bar area.
A beach with a wooden boardwalk, umbrellas, and people.

2. Hyatt Place Ocean City / Oceanfront

Hyatt Place Ocean City / Oceanfront
Downtown Ocean City
United States
Victoria
NT$3,493
NT$3,912 total
includes taxes & fees
Oct 5 - Oct 6
Hyatt Place Ocean City / Oceanfront
A large, two-story barn-style building with a covered front porch and a garage.
A dining room with a round table set for six, surrounded by wooden chairs. A fireplace with ornate details is visible, and a large mirror hangs above it.
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.

3. Kent Island Resort

Kent Island Resort
Stevensville
United States
Bethany
NT$4,856
NT$6,464 total
includes taxes & fees
Oct 12 - Oct 13
Kent Island Resort
A multi-story hotel with balconies, a beachside location, and various shops and restaurants.
An outdoor seating area with tables and chairs, overlooking a beach.
A beach with umbrellas and people.
A vibrant hotel lobby with a blue sofa, colorful artwork, a surfboard, and a modern chandelier.

4. Park Place Hotel

Park Place Hotel
Downtown Ocean City
United States
Joseph Michael
NT$2,404
NT$4,048 total
includes taxes & fees
Sep 30 - Oct 1
Park Place Hotel
A coastal hotel with multiple buildings, a beach, and a pier in the background.
A hotel room with two beds, a desk, a chair, a TV, and a view of the ocean.
An indoor swimming pool with lounge chairs and a view of the outside balconies.
A hotel named 'Courtyard by Marriott' with a beach view, outdoor seating, and multiple balconies.

5. Courtyard Ocean City Oceanfront

Courtyard Ocean City Oceanfront
Downtown Ocean City
United States
Gonzalo
NT$3,601
NT$4,033 total
includes taxes & fees
Oct 7 - Oct 8
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.
The exterior of SeaLoft Oceanfront Hotel with a prominent sign and a balcony with white railings.
A beach with numerous umbrellas and people.

6. SeaLoft Oceanfront Hotel

SeaLoft Oceanfront Hotel
Midtown Ocean City
United States
Jessica
NT$2,255
NT$2,526 total
includes taxes & fees
Oct 12 - Oct 13
SeaLoft Oceanfront Hotel
A waterfront property with a prominent building featuring a red roof and a tower, surrounded by water and marshland.
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.
A spacious lobby with wooden ceiling, comfortable seating, large windows, and a fireplace.

7. Lighthouse Club Hotel

Lighthouse Club Hotel
Midtown Ocean City
United States
Jonathan
NT$4,639
NT$5,196 total
includes taxes & fees
Oct 12 - Oct 13
Lighthouse Club Hotel
A hotel room with two beds, a desk, a chair, and a wall-mounted TV.
A modern hotel with a prominent 'Wingate by Wyndham' sign, a covered entrance, and a flag.
A reception area with a modern design, featuring a reception desk, a mounted television, a clock, and a large painting on the wall.
A hotel room with a patterned carpet, a sofa, a chair, a small table, and a lamp.

8. Wingate by Wyndham North East

Wingate by Wyndham North East
North East
United States
Gary
NT$3,029
NT$3,393 total
includes taxes & fees
Oct 4 - Oct 5
Wingate by Wyndham North East
An indoor swimming pool with clear glass walls, lounge chairs, and a view of the outside.
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.
A modern hotel room with a large window, a flat-screen TV, a blue sofa, a yellow ottoman, and a green armchair.

9. Comfort Inn Gold Coast

Comfort Inn Gold Coast
North Ocean City
United States
Nelson
NT$2,561
NT$2,869 total
includes taxes & fees
Oct 21 - Oct 22
Comfort Inn Gold Coast
A swimming pool with blue lounge chairs and striped umbrellas.
A balcony with a chair, a sliding glass door leading to a bedroom with a bed, a sofa, and a 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.

10. Hotel Monte Carlo Ocean City

Hotel Monte Carlo Ocean City
Downtown Ocean City
United States
Dennis
NT$2,255
NT$3,237 total
includes taxes & fees
Oct 11 - Oct 12
Hotel Monte Carlo Ocean City
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Top Eastern Shore Hotel Reviews

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