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

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Check availability on Eastern Shore Winery Hotels

Tonight
Sep 30 - Oct 1
Tomorrow
Oct 1 - Oct 2
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

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 reception area with a modern design, featuring a reception desk, a seating area, and a hallway leading to other rooms.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A modern lounge area with seating, a fireplace, and a television.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Amy
NT$3,307
NT$3,670 total
includes taxes & fees
Oct 25 - Oct 26
Comfort Inn & Suites Chestertown
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 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 rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.

2. Kent Island Resort

Kent Island Resort
Stevensville
United States
Bethany
NT$4,626
NT$6,208 total
includes taxes & fees
Oct 28 - Oct 29
Kent Island Resort
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.

3. Hyatt Place Ocean City / Oceanfront

Hyatt Place Ocean City / Oceanfront
Downtown Ocean City
United States
Victoria
NT$3,496
NT$3,915 total
includes taxes & fees
Oct 18 - Oct 19
Hyatt Place Ocean City / Oceanfront
A multi-story hotel with balconies, a beachside location, and various shops and restaurants.
A multi-story hotel with a pool area, including sun loungers and a smaller pool.
A beach with umbrellas and people.
An outdoor seating area with tables and chairs, overlooking a beach.

4. Park Place Hotel

Park Place Hotel
Downtown Ocean City
United States
Michelle
NT$2,174
NT$3,159 total
includes taxes & fees
Oct 12 - Oct 13
Park Place Hotel
A coastal hotel with multiple buildings, a beach, and a pier in the background.
Room
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.

5. Courtyard Ocean City Oceanfront

Courtyard Ocean City Oceanfront
Downtown Ocean City
United States
Gonzalo
NT$3,060
NT$3,428 total
includes taxes & fees
Oct 19 - Oct 20
Courtyard Ocean City Oceanfront
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.
A hotel room with a large bed, a chair, a wardrobe, and a window with a view of a green landscape.
An outdoor patio with tables and chairs, blue umbrellas, and potted plants.

6. Comfort Inn Gold Coast

Comfort Inn Gold Coast
North Ocean City
United States
Nelson
NT$2,404
NT$2,692 total
includes taxes & fees
Oct 23 - Oct 24
Comfort Inn Gold Coast
A balcony with two blue Adirondack chairs facing a beach with a white fence and a clear sky.
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.
The exterior of SeaLoft Oceanfront Hotel with a prominent sign and a balcony with white railings.

7. SeaLoft Oceanfront Hotel

SeaLoft Oceanfront Hotel
Midtown Ocean City
United States
Jessica
NT$2,260
NT$2,531 total
includes taxes & fees
Oct 18 - Oct 19
SeaLoft Oceanfront 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 hotel room with a patterned carpet, a sofa, a chair, a small table, and a lamp.
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
Gary
NT$3,130
NT$3,506 total
includes taxes & fees
Oct 25 - Oct 26
Wingate by Wyndham North East
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 bar area with stone walls, metal chairs, and two TVs mounted on the wall.
A white beach ball with "Monte Carlo Hotel Group" and "Ocean City, MD" text.

9. Hotel Monte Carlo Ocean City

Hotel Monte Carlo Ocean City
Downtown Ocean City
United States
Jacob
NT$2,268
NT$3,255 total
includes taxes & fees
Oct 15 - Oct 16
Hotel Monte Carlo Ocean City
A large, historic house with a wrap-around porch and a gazebo, surrounded by lush vegetation and a body of water.
A covered porch with wicker furniture, a small table, and a view of a green landscape and water.
A window with a view of a grassy field and trees, curtains partially drawn, and a road sign indicating a speed limit of 30.
A river with a dock, a sailboat, and a motorboat. There are buildings and trees in the background.

10. The Whitehaven Hotel

The Whitehaven Hotel
Quantico
United States
Tracy
NT$5,256
NT$5,886 total
includes taxes & fees
Oct 4 - Oct 5
The Whitehaven Hotel
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Top Eastern Shore Hotel Reviews

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