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 20 - Oct 21
Tomorrow
Oct 21 - Oct 22
This weekend
Oct 23 - Oct 25
Next weekend
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 spacious dining area with high ceilings, large windows, and modern chandeliers.
A spacious dining area with a view of the water, featuring a modern design with a marble floor and contemporary furniture.

1. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
United States
John
￥25,520
￥33,492 total
includes taxes & fees
Nov 18 - Nov 19
Hyatt Regency Chesapeake Bay
A balcony with wicker furniture and a table, overlooking a beach with umbrellas and people.
A bar area with a long counter, multiple bar stools, and a pool table. There are tables and chairs for dining, and the room has large windows.
A beachfront hotel with multiple floors and balconies, a sandy beach in the foreground, and a clear sky.
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
John
￥12,828
￥14,368 total
includes taxes & fees
Nov 2 - Nov 3
DoubleTree by Hilton Ocean City Oceanfront
A room with a fireplace, a dining area with chairs, a large window with a view of the outside, and a cabinet with bottles.
A golf course with a water hazard and surrounding trees.
A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.
A living room with a fireplace, a sofa, a coffee table, and a television mounted on the wall.

3. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
United States
Virgilio
￥77,810
￥85,591 total
includes taxes & fees
Nov 18 - Nov 19
Inn at Perry Cabin
A clear pool with palm trees, lounge chairs, and umbrellas.
A large hotel with multiple floors and balconies, situated on a beach with a clear sky.
A beachside bar with Adirondack chairs, a pool, and a view of the ocean.
A beach with a row of multi-story hotels.

4. Holiday Inn & Suites Ocean City by IHG

Holiday Inn & Suites Ocean City by IHG
Downtown Ocean City
United States
Marilyn
￥14,266
￥15,978 total
includes taxes & fees
Nov 17 - Nov 18
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 restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.
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
￥12,657
￥13,923 total
includes taxes & fees
Nov 1 - Nov 2
St Michaels Inn
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 dining area with multiple tables and chairs, wooden ceiling beams, and large windows with blinds.

6. The Tidewater Inn

The Tidewater Inn
Easton
United States
Miriam
￥26,023
￥28,626 total
includes taxes & fees
Nov 1 - Nov 2
The Tidewater Inn
A modern indoor swimming pool with clear water, a lifebuoy on the wall, and a seating area with chairs and tables.
A breakfast buffet with various food options and a sign reading "TOP IT BREAKFAST".
A 24/7 market with a variety of snacks and beverages, including chips and bottled drinks.
A modern hotel building with a prominent 'tru by Hilton' sign, multiple floors, and a parking lot.

7. Tru by Hilton Ocean City Bayside

Tru by Hilton Ocean City Bayside
Midtown Ocean City
United States
Steven
￥10,008
￥11,210 total
includes taxes & fees
Oct 27 - Oct 28
Tru by Hilton Ocean City Bayside
A balcony with a view of the sea, a pool, and a row of chairs.
A modern bar area with a long counter, multiple bar stools, and ambient lighting.
A poolside area with lounge chairs and umbrellas, reflecting the sky and clouds.
A coastal hotel with a marina, a large building with multiple floors, and a view of the city skyline in the background.

8. Residence Inn by Marriott Ocean City

Residence Inn by Marriott Ocean City
Midtown Ocean City
United States
Christina
￥14,222
￥15,928 total
includes taxes & fees
Oct 29 - Oct 30
Residence Inn by Marriott Ocean City
A resort pool area with lounge chairs, palm trees, and a boat-shaped water feature.
An aerial view of a coastal city with a beachfront hotel featuring multiple floors, a swimming pool, and a marina in the background.
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.

9. Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites
Midtown Ocean City
United States
Rosemary
￥18,133
￥20,309 total
includes taxes & fees
Nov 2 - Nov 3
Hilton Ocean City Oceanfront Suites
An outdoor seating area with tables and chairs, overlooking a body of water and greenery.
A modern lounge area with a fireplace, seating, and a view of the outdoors.
A spacious indoor dining area with large windows, tables, and chairs.
A large building with a swimming pool, dock, and green surroundings.

10. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
United States
Kelly
￥27,739
￥30,513 total
includes taxes & fees
Oct 25 - Oct 26
The Tilghman Island Inn
View all properties

Top Eastern Shore Hotel Reviews

Holiday Inn Ocean City by IHG

Holiday Inn Ocean City by IHG

10/10 Excellent
"Room was clean, bed was comfortable. Hot tubs and pools were great! When indoor hot tubs wouldn't turn on, we approached the front desk. They called maintenance before we even turned away, and he arrived to fix them as we were walking back in! Took mere seconds, and he had the jets back up and running!"
Francine 2-night trip
Posted 3 hours ago
Holiday Inn Ocean City by IHG
Fenwick Inn

Fenwick Inn

10/10 Excellent
"It was great! Clean room. Staff was great!"
Jeanne 2-night trip
Posted 14 hours ago
Fenwick Inn
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Staff was exceptional. Historical vibe was fun and coastal-appropriate. Close to DC and other fun destinations."
Kelly 4-night trip
Posted 16 hours ago
St Michaels Inn
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

8/10 Good
"We found our room to be surprisingly spacious, very clean, and comfortable; however, the kitchenette/bathroom areas were a bit dated. The property location was excellent and there were restaurants and a pool within the property. The common areas inside the hotel and the outdoor space at the front of the hotel were adequate, but guests were somewhat disrespectful, leaving their trash, not replacing chairs after their use, etc... The staff was pleasant enough when checking-in and helpful when we had a question but were ignoring simple tasks like straightening up the common areas when time allowed. Although this was a little off-putting, we would return if the opportunity presented itself."
Keli 1-night trip
Posted 1 day ago
Grand Hotel Ocean City Oceanfront

Explore a world of travel with Expedia