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 14 - Sep 15
Tomorrow
Sep 15 - Sep 16
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

Our top choices for Eastern Shore 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 vibrant hotel lobby with a blue sofa, colorful artwork, a surfboard, and a modern chandelier.

1. Park Place Hotel

Park Place Hotel
Downtown Ocean City
United States
Sieki
NT$1,914
NT$3,495 total
includes taxes & fees
Sep 29 - Sep 30
Park Place Hotel
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 hotel reception area with a modern design, featuring a reception desk, a seating area, and a hallway leading to other rooms.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.

2. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Amy
NT$3,266
NT$3,625 total
includes taxes & fees
Oct 4 - Oct 5
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 hotel room with a large bed, a desk, a chair, and a view of the city through large windows.

3. Hyatt Place Ocean City / Oceanfront

Hyatt Place Ocean City / Oceanfront
Downtown Ocean City
United States
Cynthia
NT$3,418
NT$3,828 total
includes taxes & fees
Sep 28 - Sep 29
Hyatt Place Ocean City / Oceanfront
A balcony with two blue Adirondack chairs facing a beach with a white fence and a clear sky.
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.
A beach with numerous umbrellas and people.
The exterior of SeaLoft Oceanfront Hotel with a prominent sign and a balcony with white railings.

4. SeaLoft Oceanfront Hotel

SeaLoft Oceanfront Hotel
Midtown Ocean City
United States
Raymond
NT$2,250
NT$2,520 total
includes taxes & fees
Oct 5 - Oct 6
SeaLoft Oceanfront Hotel
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 bedroom with a large bed, a bench, a dresser, and two windows with curtains.
A rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.

5. Kent Island Resort

Kent Island Resort
Stevensville
United States
Bethany
NT$4,844
NT$6,448 total
includes taxes & fees
Oct 12 - Oct 13
Kent Island Resort
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.

6. Courtyard Ocean City Oceanfront

Courtyard Ocean City Oceanfront
Downtown Ocean City
United States
Lorianne
NT$3,592
NT$4,023 total
includes taxes & fees
Oct 5 - Oct 6
Courtyard Ocean City Oceanfront
A hotel room with two beds, a desk, a chair, and a wall-mounted TV.
A hotel room with a patterned carpet, a sofa, a chair, a small table, and a lamp.
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.

7. Wingate by Wyndham North East

Wingate by Wyndham North East
North East
United States
Gary
NT$3,190
NT$3,573 total
includes taxes & fees
Oct 4 - Oct 5
Wingate by Wyndham North East
A swimming pool with blue lounge chairs and striped umbrellas.
A white beach ball with "Monte Carlo Hotel Group" and "Ocean City, MD" text.
A balcony with a chair, a sliding glass door leading to a bedroom with a bed, a sofa, and a lamp.
A bar area with stone walls, metal chairs, and two TVs mounted on the wall.

8. Hotel Monte Carlo Ocean City

Hotel Monte Carlo Ocean City
Downtown Ocean City
United States
Lisa
NT$2,204
NT$3,178 total
includes taxes & fees
Oct 11 - Oct 12
Hotel Monte Carlo Ocean City
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.

9. Comfort Inn Gold Coast

Comfort Inn Gold Coast
North Ocean City
United States
Thomas
NT$2,595
NT$2,907 total
includes taxes & fees
Oct 14 - Oct 15
Comfort Inn Gold Coast
A waterfront property with a prominent building featuring a red roof and a tower, surrounded by water and marshland.
A restaurant with large windows offering a view of the sea. Tables are set with white tablecloths and wooden chairs.
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.

10. Lighthouse Club Hotel

Lighthouse Club Hotel
Midtown Ocean City
United States
Alex
NT$4,628
NT$5,184 total
includes taxes & fees
Oct 12 - Oct 13
Lighthouse Club Hotel
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Top Eastern Shore Hotel Reviews

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