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

Find Romantic Hotels in Eastern Shore, MD

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Eastern Shore Romantic Hotels

Tonight
Oct 17 - Oct 18
Tomorrow
Oct 18 - Oct 19
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Our top choices for Eastern Shore romantic hotels

An indoor swimming pool with lounge chairs and tables, large windows, and a high wooden ceiling.
A spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.
A marina with boats docked, a large building with a tower in the background, and a dock extending into the water.
A marina with boats docked, a sandy beach, and a clear blue sky.

1. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
United States
John
₩253,508
₩325,839 total
includes taxes & fees
Nov 10 - Nov 11
Hyatt Regency Chesapeake Bay
A rooftop lounge area with seating and tables, surrounded by high-rise buildings.
A balcony with wicker furniture and a table, overlooking a beach with umbrellas and people.
A living room with a beige sofa, blue and red patterned pillows, a wooden coffee table, and a view of the ocean through large windows.
A swimming pool with lounge chairs and umbrellas, surrounded by large windows and a glass ceiling.

2. DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
Midtown Ocean City
United States
Darryl
₩108,314
₩121,312 total
includes taxes & fees
Nov 2 - Nov 3
DoubleTree by Hilton Ocean City Oceanfront
A large, stately house with a grand entrance, multiple windows, and a symmetrical facade.
An indoor corridor with brick walls, a brick floor, and a sign reading "DECANTER WINE ROOM".
A bedroom with a large bed, a nightstand, a lamp, and a window with blinds.
A spacious living room with a leather sofa, a coffee table, and a bookshelf filled with books.

3. The Tidewater Inn

The Tidewater Inn
Easton
United States
Miriam
₩238,831
₩262,715 total
includes taxes & fees
Nov 1 - Nov 2
The Tidewater Inn
A clear pool with palm trees, lounge chairs, and umbrellas.
A beachside bar with Adirondack chairs, a pool, and a view of the ocean.
A beach with a row of multi-story hotels.
A balcony table with breakfast items and a view of the ocean.

4. Holiday Inn & Suites Ocean City by IHG

Holiday Inn & Suites Ocean City by IHG
Downtown Ocean City
United States
Jacqueline
₩120,083
₩134,493 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn & Suites Ocean City by IHG
A two-story building with a covered entrance and an American flag.
A hotel room with two beds, a chair, and a painting on the wall.
A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.
A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.

5. St Michaels Inn

St Michaels Inn
St. Michaels
United States
Lynn
₩106,873
₩117,561 total
includes taxes & fees
Nov 1 - Nov 2
St Michaels Inn
A room with a view of a wooden deck and a gazebo by the water.
A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.
A hotel room with a large bed, a chair, a desk, and a television.
A golf course with a water hazard and surrounding trees.

6. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
United States
Virgilio
₩708,487
₩779,336 total
includes taxes & fees
Nov 3 - Nov 4
Inn at Perry Cabin
A modern indoor swimming pool with clear water, a lifebuoy on the wall, and a seating area with chairs and tables.
A modern hotel building with a prominent 'tru by Hilton' sign, multiple floors, and a parking lot.
A 24/7 market with a variety of snacks and beverages, including chips and bottled drinks.
A breakfast buffet with various food options and a sign reading "TOP IT BREAKFAST".

7. Tru by Hilton Ocean City Bayside

Tru by Hilton Ocean City Bayside
Midtown Ocean City
United States
kimberly
₩83,764
₩93,816 total
includes taxes & fees
Oct 25 - Oct 26
Tru by Hilton Ocean City Bayside
A resort pool area with lounge chairs, palm trees, and a boat-shaped water feature.
A balcony with a round table and chairs, overlooking the beach and ocean.
A dining table set with wine glasses, a bottle of Riesling wine, a vase with flowers, and a basket of bread.
A large, multi-story hotel with a prominent Hilton sign, a parking lot with several cars, and a view of the ocean in the background.

8. Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites
Midtown Ocean City
United States
Macey
₩153,105
₩171,477 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Ocean City Oceanfront Suites
An indoor swimming pool with clear water, tiled steps, and orange lounge chairs.
A modern house with a glass door entrance, outdoor seating area with chairs, and a small table.
A modern lounge area with multiple seating arrangements, including sofas and chairs, a central wooden planter, and ambient lighting.
A hotel reception area with a herringbone patterned floor, reception desks, a flat-screen TV, and a view of the lobby.

9. Fenwick Inn

Fenwick Inn
North Ocean City
United States
Shaun
₩82,857
₩112,748 total
includes taxes & fees
Nov 2 - Nov 3
Fenwick Inn
A balcony with a view of the sea, a pool, and a row of chairs.
A poolside area with lounge chairs and umbrellas, reflecting the sky and clouds.
A modern hotel lobby with a glass railing, a blue-lit water feature, and a wooden wall.
A coastal hotel with a marina, a large building with multiple floors, and a view of the city skyline in the background.

10. Residence Inn by Marriott Ocean City

Residence Inn by Marriott Ocean City
Midtown Ocean City
United States
Christina
₩120,083
₩134,493 total
includes taxes & fees
Oct 21 - Oct 22
Residence Inn by Marriott Ocean City
View all properties

Top Eastern Shore Hotel Reviews

Holiday Inn & Suites Ocean City by IHG

Holiday Inn & Suites Ocean City by IHG

8/10 Good
"Great oceanfront location suites were clean & spacious whirlpool tub was a plus will definitely be staying there again"
Marilyn 3-night trip
Posted 17 hours ago
Holiday Inn & Suites Ocean City by IHG
Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel

Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel

10/10 Excellent
"The staff was amazing !!!!"
Colleen 2-night trip
Posted 23 hours ago
Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel
St Michaels Inn

St Michaels Inn

8/10 Good
"We have stayed here quite a few times oner the last 15 or so years. The owners seem to always do work to make it better since the property is not a newer motel. The exterior shows the efforts. The interior is the main concern. The typical cleaning is fine in the high traffic areas, but fine detailing and dusting is non-existent and it's been this way for years. You can usually write you name in the dust on lamps and other items. Normally I would ding this level a cleaning two stars, but the room rates, especially off season, keeps the 4-star rating. Breakfast is in a large room and well stocked. Depending on the vacancy rate, there can be hot eggs and sausage. Otherwise, a fairly hefty continental breakfast. I do have to give a plug for the coffee and that also keeps a for star rating. Their coffee in the breakfast room is excellent compared to most hotels/motels where it is notoriously bad, which I never understood. For java drinkers, it means the difference between starting you day off in a positive or negative way. Never understood why hotels provide bad coffee. It leaves a bad taste in your mouth (pun intended)."
Ben 2-night trip
Posted 1 day ago
St Michaels Inn
Carousel Resort Hotel & Condominiums

Carousel Resort Hotel & Condominiums

8/10 Good
"The room that we stayed in could have used a little cleaning. There was dust and a build up on top of the vents. A visible mold was visible at the base of the vertical blinds by the door leading to the balcony."
Michael 3-night trip
Posted 1 day ago
Carousel Resort Hotel & Condominiums

Explore a world of travel with Expedia