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 8 - Oct 9
Tomorrow
Oct 9 - Oct 10
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Eastern Shore romantic hotels

A large, stately house with a grand entrance, multiple windows, and a symmetrical facade.
A spacious living room with a leather sofa, a coffee table, and a bookshelf filled with books.
A bedroom with a large bed, a nightstand, a lamp, and a window with blinds.
An indoor corridor with brick walls, a brick floor, and a sign reading "DECANTER WINE ROOM".

1. The Tidewater Inn

The Tidewater Inn
Easton
United States
Miriam
₩239,860
₩263,846 total
includes taxes & fees
Nov 1 - Nov 2
The Tidewater Inn
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 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
₩108,781
₩121,835 total
includes taxes & fees
Nov 1 - Nov 2
DoubleTree by Hilton Ocean City Oceanfront
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 spacious dining area with high ceilings, large windows, and modern chandeliers.

3. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
United States
John
₩238,520
₩308,991 total
includes taxes & fees
Nov 4 - Nov 5
Hyatt Regency Chesapeake Bay
An indoor swimming pool with clear water, tiled steps, and orange lounge chairs.
A hotel room with two beds, a large window with a city view, a flat-screen TV, and a desk with a lamp.
A hotel reception area with a herringbone patterned floor, reception desks, a flat-screen TV, and a view of the lobby.
A modern lounge area with multiple seating arrangements, including sofas and chairs, a central wooden planter, and ambient lighting.

4. Fenwick Inn

Fenwick Inn
North Ocean City
United States
Lilian
₩83,214
₩113,233 total
includes taxes & fees
Oct 26 - Oct 27
Fenwick Inn
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 waterfront property with a dock, a sailboat, and a building with a red roof.
A spacious indoor dining area with large windows, tables, and chairs.

5. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
United States
William
₩247,900
₩272,690 total
includes taxes & fees
Oct 12 - Oct 13
The Tilghman Island Inn
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 restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.

6. St Michaels Inn

St Michaels Inn
St. Michaels
United States
Lynn
₩119,394
₩131,333 total
includes taxes & fees
Oct 11 - Oct 12
St Michaels Inn
A hotel with a pool, beachside seating, and high-rise buildings in the background.
A restaurant with tables set for dining, large windows with ocean views, and blue umbrellas.
A spacious indoor area with wooden tables, potted plants, and modern furniture.
A bar area with seating, a bar counter, and a view of the ocean.

7. Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel

Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel
North Ocean City
United States
Tiffany
₩97,903
₩109,653 total
includes taxes & fees
Nov 1 - Nov 2
Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel
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 golf course with a water hazard and surrounding trees.
A hotel room with a large bed, a chair, a desk, and a television.

8. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
United States
Virgilio
₩687,420
₩756,162 total
includes taxes & fees
Nov 8 - Nov 9
Inn at Perry Cabin
A resort pool area with lounge chairs, palm trees, and a boat-shaped water feature.
A dining table set with wine glasses, a bottle of Riesling wine, a vase with flowers, and a basket of bread.
An aerial view of a coastal city with a beachfront hotel featuring multiple floors, a swimming pool, and a marina in the background.
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.

9. Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites
Midtown Ocean City
United States
Bobbi
₩153,765
₩172,217 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Ocean City Oceanfront Suites
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 beach with a row of multi-story hotels.
A balcony table with breakfast items and a view of the ocean.

10. Holiday Inn & Suites Ocean City by IHG

Holiday Inn & Suites Ocean City by IHG
Downtown Ocean City
United States
Jacqueline
₩125,960
₩141,074 total
includes taxes & fees
Nov 8 - Nov 9
Holiday Inn & Suites Ocean City by IHG
View all properties

Top Eastern Shore Hotel Reviews

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

10/10 Excellent
"Beautiful clean room right on the ocean! We will be returning!"
Tammy 4-night trip
Posted 3 hours ago
Princess Royale Oceanfront Resort
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Late night manager was extremely helpful!"
Rodney 1-night trip
Posted 7 days ago
St Michaels Inn

Explore a world of travel with Expedia