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

Eastern Shore Hotels with Bars / Lounges

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Check availability on Eastern Shore Hotels with Bars / Lounges

Tonight
6 Sept - 7 Sept
Tomorrow
7 Sept - 8 Sept
Next weekend
11 Sept - 13 Sept
In two weeks
18 Sept - 20 Sept

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 bedroom with a large bed, a nightstand, a lamp, and a window with blinds.
A spacious living room with a leather sofa, a coffee table, and a bookshelf filled with books.
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
RM764
RM841 total
includes taxes & fees
29 Sept - 30 Sept
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.
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.
An outdoor event area with round tables and a view of the water.

2. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
United States
Karen
RM615
RM682 total
includes taxes & fees
4 Oct - 5 Oct
Hyatt Place Kent Narrows & Marina
A patio with outdoor seating, overlooking a marina with boats.
A waterfront hotel with multiple balconies, a marina with yachts, and a well-lit exterior.
An indoor swimming pool with clear views of boats and water.
A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.

3. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
United States
roney
RM594
RM659 total
includes taxes & fees
4 Oct - 5 Oct
Hilton Garden Inn Kent Island Marina
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 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.
A dark wooden panel wall with a mounted flat-screen TV, a bench with cushions, and a small plant in a vase.

4. The Wildset

The Wildset
Downtown St. Michaels
United States
Paula
RM967
RM1,164 total
includes taxes & fees
22 Sept - 23 Sept
The Wildset
A multi-story hotel with a pool area, balconies, and a view of the ocean.
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.
A wooden boardwalk leading to a beachfront hotel with multiple balconies and a clear view of the ocean.

5. Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront
Downtown Ocean City
United States
Tash
RM346
RM387 total
includes taxes & fees
5 Oct - 6 Oct
Grand Hotel Ocean City Oceanfront
An indoor swimming pool with lounge chairs and tables, large windows, and a high wooden ceiling.
A spacious dining area with high ceilings, large windows, and modern chandeliers.
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.

6. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
United States
Naomi
RM930
RM1,249 total
includes taxes & fees
7 Sept - 8 Sept
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 bed, two blue chairs, a table, and a view of the beach.
A restaurant with a high ceiling, large windows, and a view of the sunset.

7. Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort
North Ocean City
United States
Cesar
RM440
RM557 total
includes taxes & fees
4 Oct - 5 Oct
Princess Royale Oceanfront Resort
An indoor swimming pool with clear water, tiled steps, and orange lounge chairs.
A modern lounge area with multiple seating arrangements, including sofas and chairs, a central wooden planter, and ambient lighting.
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.

8. Fenwick Inn

Fenwick Inn
North Ocean City
United States
Lilian
RM288
RM383 total
includes taxes & fees
21 Sept - 22 Sept
Fenwick Inn
A beach scene with two beach chairs labeled "Castle in the Sand" and a person under a blue umbrella.
A hotel room with a bed, a wall-mounted lamp, an air conditioner, and a view of the beach.
A beachside restaurant with outdoor seating and umbrellas.
A castle-like building with a swimming pool, surrounded by trees and illuminated by street lights.

9. Castle in the Sand

Castle in the Sand
Midtown Ocean City
United States
Taylor
RM240
RM268 total
includes taxes & fees
7 Sept - 8 Sept
Castle in the Sand
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 dining area with round tables, high ceilings with ductwork, and a stone fireplace.

10. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
United States
scott
RM774
RM961 total
includes taxes & fees
8 Sept - 9 Sept
The Inn at Chesapeake Bay Beach Club
View all properties

Top Eastern Shore Hotel Reviews

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

10/10 Excellent
"The place was great. Every room is like a 1 bedroom apartment with a full kitchen. The price was great for what you are getting."
Thomas 4-night trip
Posted 4 hours ago
Princess Royale Oceanfront Resort
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

10/10 Excellent
"Clean friendly and pool restaurant every thing right there"
jean 1-night trip
Posted 5 hours ago
Grand Hotel Ocean City Oceanfront
Castle in the Sand

Castle in the Sand

10/10 Excellent
"Great place to stay staff friendly very helpful two restaurants on site ocean view cannot be beat and cheaper than a lot of other options in the area. I highly highly recommend"
Reginald 2-night trip
Posted 7 hours ago
Castle in the Sand
Crystal Beach Hotel

Crystal Beach Hotel

10/10 Excellent
"The check-in was smooth and quick the room was nice its right on the boardwalk and close to many places to eat. I enjoyed it."
Eric 1-night trip
Posted 13 hours ago
Crystal Beach Hotel
Princess Bayside Beach Hotel

Princess Bayside Beach Hotel

8/10 Good
"We stayed in a bayfront balcony room, and the view was absolutely amazing. The small private beach on the bay was a wonderful bonus and a great place to relax. We also really enjoyed the rooftop pool, which offered stunning bay views as well. The room itself was comfortable, although a bit dated. That said, it certainly wasn't anything that would keep us from returning. If you're looking for a very quiet retreat, however, this may not be the best fit. We found the air conditioning unit to be quite loud, and noise traveled easily throughout the building. Room doors tended to slam, the elevator's chime could be heard frequently, and hallway conversations and footsteps were surprisingly noticeable from inside the room. While those are important things to mention, they didn't detract significantly from our overall experience. The incredible view, convenient bay access, and private beach more than made up for the noise. We thoroughly enjoyed our stay and would definitely come back."
Sherri 5-night trip
Posted 14 hours ago
Princess Bayside Beach Hotel
Fenwick Inn

Fenwick Inn

10/10 Excellent
"Great"
Yunshen 7-night trip
Posted 22 hours ago
Fenwick Inn

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