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

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Check availability on Eastern Shore Romantic Hotels

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

Our top choices for Eastern Shore romantic hotels

A large, stately house with a grand entrance, multiple windows, and a symmetrical facade.
A spacious dining area with multiple tables and chairs, wooden ceiling beams, and large windows with blinds.
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
AED 611
AED 673 total
includes taxes & fees
1 Nov - 2 Nov
The Tidewater Inn
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.

2. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
United States
John
AED 698
AED 897 total
includes taxes & fees
10 Nov - 11 Nov
Hyatt Regency Chesapeake Bay
A room with a view of a wooden deck and a gazebo by the water.
A hotel room with a large bed, a chair, a desk, and a television.
A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.
A golf course with a water hazard and surrounding trees.

3. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
United States
Virgilio
AED 1,950
AED 2,145 total
includes taxes & fees
3 Nov - 4 Nov
Inn at Perry Cabin
An outdoor seating area with tables and chairs, overlooking a body of water and greenery.
A waterfront property with a dock, a sailboat, and a building with a red roof.
A large building with a swimming pool, dock, and green surroundings.
A spacious indoor dining area with large windows, tables, and chairs.

4. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
United States
William
AED 680
AED 747 total
includes taxes & fees
19 Oct - 20 Oct
The Tilghman Island Inn
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.
A beachfront hotel with multiple floors and balconies, a sandy beach in the foreground, and a clear sky.

5. DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
Midtown Ocean City
United States
Darryl
AED 298
AED 334 total
includes taxes & fees
1 Nov - 2 Nov
DoubleTree by Hilton Ocean City Oceanfront
A lakeside view with sailboats, grassy areas, and white Adirondack chairs.
A waterfront bar with outdoor seating, a view of the water, and American flags.
A bottle of Merlot wine and two glasses on a wooden tray by a window overlooking a lake.
A beach with clear water, sandy shore, and some vegetation.

6. Sandaway Suites & Beach

Sandaway Suites & Beach
Oxford
United States
Gary
AED 1,108
AED 1,218 total
includes taxes & fees
17 Nov - 18 Nov
Sandaway Suites & Beach
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 house with a glass door entrance, outdoor seating area with chairs, and a small table.

7. Fenwick Inn

Fenwick Inn
North Ocean City
United States
Shaun
AED 228
AED 310 total
includes taxes & fees
2 Nov - 3 Nov
Fenwick Inn
A modern indoor swimming pool with clear water, a lifebuoy on the wall, and a seating area with chairs and tables.
A 24/7 market with a variety of snacks and beverages, including chips and bottled drinks.
A modern reception area with a curved desk, seating, and a view of the outdoors.
A breakfast buffet with various food options and a sign reading "TOP IT BREAKFAST".

8. Tru by Hilton Ocean City Bayside

Tru by Hilton Ocean City Bayside
Midtown Ocean City
United States
kimberly
AED 226
AED 253 total
includes taxes & fees
25 Oct - 26 Oct
Tru by Hilton Ocean City Bayside
A two-story building with a covered entrance and an American flag.
A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.
A hotel room with two beds, a chair, and a painting on the wall.
A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.

9. St Michaels Inn

St Michaels Inn
St. Michaels
United States
Lynn
AED 294
AED 324 total
includes taxes & fees
1 Nov - 2 Nov
St Michaels Inn
A large, two-story Victorian-style house with a prominent tower, multiple windows, and a porch.
A turquoise bicycle with a basket and a seat, parked on a paved path with a sign for Hummingbird Inn in the background.
A bedroom with a sloped ceiling, a wooden bed, a desk with a lamp, and a dresser.
A living room with a sofa, a chair, a small table with a plant, and a window with a view of buildings.

10. Hummingbird Inn

Hummingbird Inn
Easton
United States
Ann
AED 1,088
AED 1,238 total
includes taxes & fees
19 Oct - 20 Oct
Hummingbird Inn
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Top Eastern Shore Hotel Reviews

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 12 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 14 hours 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 15 hours ago
Carousel Resort Hotel & Condominiums

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