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

Find Hotels with Bars 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 Hotels with Bars

Tonight
1 Oct - 2 Oct
Tomorrow
2 Oct - 3 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Eastern Shore hotels with a bar

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
AED 618
AED 680 total
includes taxes & fees
1 Nov - 2 Nov
The Tidewater Inn
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.
Marina
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

2. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
United States
Karen
AED 558
AED 620 total
includes taxes & fees
13 Oct - 14 Oct
Hyatt Place Kent Narrows & Marina
A multi-story hotel with a pool area, balconies, and a view of the ocean.
A hotel room with two beds, a balcony, a dining area, and a view of the city.
A hotel room with a large bed, two chairs, a desk, and a view of the city through the window.
A lobby with green sofas, a round table with a plant, and a lantern.

3. Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront
Downtown Ocean City
United States
Tash
AED 218
AED 244 total
includes taxes & fees
1 Nov - 2 Nov
Grand Hotel Ocean City Oceanfront
A patio with outdoor seating, overlooking a marina with boats.
A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.
An indoor swimming pool with clear views of boats and water.
A waterfront hotel with multiple balconies, a marina with yachts, and a well-lit exterior.

4. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
United States
roney
AED 539
AED 598 total
includes taxes & fees
12 Oct - 13 Oct
Hilton Garden Inn Kent Island Marina
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.
A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.
A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

5. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
United States
scott
AED 702
AED 873 total
includes taxes & fees
19 Oct - 20 Oct
The Inn at Chesapeake Bay Beach Club
An indoor swimming pool with lounge chairs and tables, large windows, and a high wooden ceiling.
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.
A spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.

6. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
United States
John
AED 735
AED 1,009 total
includes taxes & fees
27 Oct - 28 Oct
Hyatt Regency Chesapeake Bay
A beachfront hotel with multiple floors, balconies, and a large glass facade.
A multi-level hotel with a central pool area, multiple balconies, and indoor seating areas.
A hotel room with a large bed, a bench, a nightstand, and a view of the ocean.
A hotel room with a bed, two blue chairs, a table, and a view of the beach.

7. Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort
North Ocean City
United States
John
AED 337
AED 436 total
includes taxes & fees
18 Oct - 19 Oct
Princess Royale Oceanfront Resort
A two-story house with a porch, a front door, and a small garden area.
A restaurant with long tables set for dining, benches along the walls, and large windows allowing natural light.
A dark wooden panel wall with a mounted flat-screen TV, a bench with cushions, and a small plant in a vase.
A neatly made bed with white linens and a beige pillow, a straw hat on the bed, a wooden nightstand with a small plant and a glass, and a wall-mounted light fixture.

8. The Wildset

The Wildset
Downtown St. Michaels
United States
Sarah
AED 878
AED 1,057 total
includes taxes & fees
20 Oct - 21 Oct
The Wildset
A multi-story hotel with balconies, located near a waterfront.
A person sitting by a poolside with orange chairs and a drink.
A modern bar area with a circular counter, bar stools, and a seating area with a view of bicycles outside.
A balcony with white railings and orange chairs, overlooking a body of water and a distant shoreline.

9. Cambria Hotel Ocean City - Bayfront

Cambria Hotel Ocean City - Bayfront
Downtown Ocean City
United States
Brittany
AED 306
AED 397 total
includes taxes & fees
26 Oct - 27 Oct
Cambria Hotel Ocean City - Bayfront
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.

10. DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
Midtown Ocean City
United States
Darryl
AED 328
AED 368 total
includes taxes & fees
1 Nov - 2 Nov
DoubleTree by Hilton Ocean City Oceanfront
View all properties

Top Eastern Shore Hotel Reviews

Quality Inn Oceanfront

Quality Inn Oceanfront

10/10 Excellent
"Fantastic as always. My only mild complaint is I wish they'd update their showers. Water pressure wasn't great and neither was the temperature control. HOWEVER I love this hotel. The staff is wonderful, rooms are a good size, great view from the ocean front side and my family LOVES the birds. Fantastic deal for the price."
Abbey 1-night trip
Posted 2 hours ago
Quality Inn Oceanfront
Bonita Beach Hotel

Bonita Beach Hotel

10/10 Excellent
"Clean rooms. Clean property."
Joshua 4-night trip
Posted 3 hours ago
Bonita Beach Hotel
Castle in the Sand

Castle in the Sand

8/10 Good
"The beach view was amazing although the balcony is only made for 2 people to use at a time. Although the ac unit is necessary, it was loud and hot when sitting on the balcony with the little space available on the balcony for the 2 chairs and one small table. Try the breakfast buffet and go Hungry! You will not regret it, and you definitely get your monies worth! The rooms are cozy. It is not new or boujee, but it is clean and nothing major to complain about. Coconuts bar was nice and the happy hour special is two for one drinks!! WIN!! Guests of Hotel get in at 4:45 and you get to beat the outsiders for seats and drinks :) We were there for our 24th wedding anniversary during the 2026 Nor' Eastern and made the best of it! We will be back!"
Lawrence 4-night trip
Posted 4 hours ago
Castle in the Sand
Crystal Beach Hotel

Crystal Beach Hotel

10/10 Excellent
"Everything was great, front desk was very helpful"
Hilda 1-night trip
Posted 9 hours ago
Crystal Beach Hotel
Carousel Resort Hotel & Condominiums

Carousel Resort Hotel & Condominiums

10/10 Excellent
"My sister in law and I spent Sept 21-26 2026 for a girls trip. We were pleased with our ocean front balcony room and appreciated having the restaurant, indoor pool and hot tub on premises. We were there during the Sept nor'easter so not having to leave the hotel to eat was very nice. All the staff were polite and friendly. We plan to come again hoping to be able to enjoy the beach next time."
Teresa 4-night trip
Posted 23 hours ago
Carousel Resort Hotel & Condominiums

Explore a world of travel with Expedia