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
Oct 15 - Oct 16
Tomorrow
Oct 16 - Oct 17
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Eastern Shore romantic hotels

A spacious lobby with a central fountain, a grand chandelier, and a curved staircase.
A storefront with a sign reading "Jerry Longo's meatballs & martinis."
A round wooden table with four plates of food, cutlery, and glasses.
A modern lounge area with sofas and a large mural of a tropical landscape.

1. Bally's Dover Casino Resort

Bally's Dover Casino Resort
Dover
United States
michael
₩108,742
₩147,557 total
includes taxes & fees
Oct 18 - Oct 19
Bally's Dover Casino Resort
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 sandy beach, and a clear blue sky.
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
₩232,469
₩302,230 total
includes taxes & fees
Nov 8 - Nov 9
Hyatt Regency Chesapeake Bay
A two-story building with a covered entrance and an American flag.
A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.
A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.
A hotel room with two beds, a chair, and a painting on the wall.

3. St Michaels Inn

St Michaels Inn
St. Michaels
United States
Lynn
₩107,546
₩118,301 total
includes taxes & fees
Nov 1 - Nov 2
St Michaels 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 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.

4. DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
Midtown Ocean City
United States
Darryl
₩108,996
₩122,076 total
includes taxes & fees
Nov 1 - Nov 2
DoubleTree by Hilton Ocean City Oceanfront
A modern outdoor seating area with striped sofas and a central fire pit.
A modern dining area with a wooden table, two gold vases, and six upholstered chairs.
A modern hotel room with a large bed, a sofa, a TV, and a dining table.
A modern hotel room with a sofa, a small table, a bed with a headboard, a kitchen area with a refrigerator, a coffee maker, and a view of the outside.

5. Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton
Fenwick Island
United States
Richard
₩130,036
₩145,640 total
includes taxes & fees
Oct 18 - Oct 19
Fenwick Shores, Tapestry Collection by Hilton
A hot tub in a room with large windows overlooking a water body and grassy area.
A view of a pier extending into calm water, viewed from a room with a table and a vase.
A covered outdoor seating area with wicker furniture and a view of a calm body of water.
A gym with exercise equipment, a hot tub, and a wicker chair.

6. Waterside Inn

Waterside Inn
Downtown Chincoteague
United States
Willard
₩82,170
₩92,278 total
includes taxes & fees
Oct 19 - Oct 20
Waterside 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.

7. The Tidewater Inn

The Tidewater Inn
Easton
United States
Miriam
₩240,334
₩264,368 total
includes taxes & fees
Nov 1 - Nov 2
The Tidewater Inn
A room with a view of a wooden deck and a gazebo by the water.
A living room with a fireplace, a sofa, a coffee table, and a television mounted on the wall.
A golf course with a water hazard and surrounding trees.
A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.

8. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
United States
Virgilio
₩712,948
₩784,243 total
includes taxes & fees
Nov 3 - Nov 4
Inn at Perry Cabin
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 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.

9. Fenwick Inn

Fenwick Inn
North Ocean City
United States
Keith
₩83,379
₩113,456 total
includes taxes & fees
Oct 28 - Oct 29
Fenwick Inn
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.

10. Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites
Midtown Ocean City
United States
Macey
₩154,069
₩172,559 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Ocean City Oceanfront Suites
View all properties

Top Eastern Shore Hotel Reviews

Holiday Inn & Suites Ocean City by IHG

Holiday Inn & Suites Ocean City by IHG

10/10 Excellent
"The rooms were very clean and the ocean front balcony view was amazing. The staff was also amazing, from housekeeping to the onsite restaurant. Our stay was mid-October but we plan to return next summer. Would give a rating of 20/10! The shower was in a jucuzzi tub. Ok, but would rather have a walk in shower."
Cindy 3-night trip
Posted 3 hours ago
Holiday Inn & Suites Ocean City by IHG
Comfort Suites Ocean City West

Comfort Suites Ocean City West

10/10 Excellent
"Easy check in safe parking quiet"
Susan 1-night trip
Posted 4 hours ago
Comfort Suites Ocean City West
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

8/10 Good
"Grand terrace restaurant was a complete disaster. Wait time was incredibly long for a waitress. After 15 minutes arrived at table took my order never returned with drinks. Meanwhile watched her serve coffee to a table that walked in right before us and even refilled there coffees. Us and another man both left without food. Restaurant was horribly understaffed. I would strongly suggest going to another establishment in area. Plenty of choices"
ANTHONY 3-night trip
Posted 4 hours ago
Grand Hotel Ocean City Oceanfront
Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel

Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel

10/10 Excellent
"This was our first time staying at this resort. I would highly recommend it. Everyone was very pleasant and helpful, the cleaning staff was very friendly and accommodating. Tap Room food was fast and hot."
Kathy 3-night trip
Posted 1 day ago
Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel
St Michaels Inn

St Michaels Inn

10/10 Excellent
"It was extremely helpful to my mobility challenged companion to have a parking space right in front of the room. The lobby area was charming, comfortable with fresh coffee, particularly helpful when we had to wait for a tow truck driver for our disabled car. The staff member Alison provided help in a variety of ways, local auto shop, contact with a driver, fresh coffee, etc."
Mary 1-night trip
Posted 3 days ago
St Michaels Inn

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