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

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Check availability on Eastern Shore Luxury Hotels

Tonight
Sep 28 - Sep 29
Tomorrow
Sep 29 - Sep 30
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Eastern Shore luxury hotels

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 golf course with a water hazard and surrounding trees.
A living room with a fireplace, a sofa, a coffee table, and a television mounted on the wall.

1. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
  • Waterfront luxury awaits with golf, spa, and marina at this St. Michaels coastal retreat.
₩694,638
₩764,102 total
includes taxes & fees
Oct 26 - Oct 27
Inn at Perry Cabin
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.

2. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
  • Chesapeake Bay resort offers luxury with private beach, full-service spa, and championship golf.
₩281,647
₩384,258 total
includes taxes & fees
Oct 26 - Oct 27
Hyatt Regency Chesapeake Bay
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.

3. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
₩258,966
₩321,901 total
includes taxes & fees
Oct 19 - Oct 20
The Inn at Chesapeake Bay Beach Club
A wooden dock with a bench and a wooden post with a light fixture.
A wooden dock leading to a house with a lawn and a pond.
A corner room with a window overlooking a green field, a wooden barrel, a chair, and a small table with a candle and flowers.
A fire pit surrounded by two white chairs with blue cushions, a small table, and potted plants.

4. Marvel's on the Creek

Marvel's on the Creek
East New Market
₩270,814
₩300,603 total
includes taxes & fees
Sep 29 - Sep 30
Marvel's on the Creek
A resort pool area with lounge chairs, palm trees, and a boat-shaped water feature.
An aerial view of a coastal city with a beachfront hotel featuring multiple floors, a swimming pool, and a marina in the background.
A balcony with a round table and chairs, overlooking the beach and ocean.
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.

5. Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites
Midtown Ocean City
₩183,206
₩205,190 total
includes taxes & fees
Oct 25 - Oct 26
Hilton Ocean City Oceanfront Suites
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 swimming pool with lounge chairs and umbrellas, surrounded by large windows and a glass ceiling.
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.

6. DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
Midtown Ocean City
₩132,130
₩147,986 total
includes taxes & fees
Oct 12 - Oct 13
DoubleTree by Hilton Ocean City Oceanfront
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.
A white colonial-style house with a covered porch, brick steps, and outdoor seating.
A deck with wicker furniture, a table, and an umbrella, overlooking a lake with trees and a dock.
A banquet hall with round tables set for dining, large windows with a view of a lake, and white chairs.

7. The Oaks Waterfront

The Oaks Waterfront
Easton
₩595,926
₩655,519 total
includes taxes & fees
Sep 30 - Oct 1
The Oaks Waterfront
A brick pathway leading to a pool area with a fence and potted plants.
A living room with a flat-screen TV on a wooden cabinet, a coffee machine on a shelf, and a door leading to another room.
A bedroom with a bed, a desk, a chair, a ceiling fan, and a patterned rug.
A dining room with a large wooden table, matching chairs, a chandelier, and a patterned rug.

8. Cypress River Inn & Spa

Cypress River Inn & Spa
Snow Hill
₩291,017
₩325,939 total
includes taxes & fees
Sep 29 - Sep 30
Cypress River Inn & Spa
A courtyard with a brick building, potted plants, and a well-lit outdoor area.
A luxurious lobby with a high ceiling, ornate chandeliers, plush seating, and a large plant.
A building with large windows, outdoor seating, and a staircase.
A lobby with a red carpet, two sofas with cushions, a large plant, and a fireplace.

9. The Ivy Hotel

The Ivy Hotel
Midtown
  • Indulgent Baltimore retreat offering historic charm, a full-service spa, and fine dining.
₩968,837
₩1,138,383 total
includes taxes & fees
Oct 1 - Oct 2
The Ivy Hotel
A modern building with a bar area, outdoor seating, and a pool.
A spa room with cushioned seating, a glass door leading outside, and a ceiling light fixture.
A modern dining area with a large table, chairs, and a view of a cityscape through large windows.
A hotel lobby with a reflective floor, a reception desk, and a large floral arrangement.

10. Four Seasons Hotel Baltimore

Four Seasons Hotel Baltimore
Harbor East
  • Indulgent waterfront retreat with 5 restaurants and a full-service spa offers a lavish Baltimore experience in Harbor East.
₩639,798
₩751,763 total
includes taxes & fees
Oct 4 - Oct 5
Four Seasons Hotel Baltimore
View all properties

Top Eastern Shore Hotel Reviews

Quality Inn Oceanfront

Quality Inn Oceanfront

8/10 Good
"bathroom tub and fixtures needs to be upgraded. Staff is both courtesy and helpful."
Robin 2-night trip
Posted 16 hours ago
Quality Inn Oceanfront
Plim Plaza Hotel

Plim Plaza Hotel

8/10 Good
"The staff was great. The bathroom had some dirt in the corners, but otherwise was clean. In the windowsill there was evidence of mice. The fridge and TV worked great, and the beds were comfortable. The location is excellent, and the view from the window was nice."
David 2-night trip
Posted 22 hours ago
Plim Plaza Hotel

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