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

Find Luxury Hotels 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 Luxury Hotels

Tonight
Oct 1 - Oct 2
Tomorrow
Oct 2 - Oct 3
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 swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.
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.
₩720,832
₩792,915 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 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 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.
₩270,798
₩371,941 total
includes taxes & fees
Oct 27 - Oct 28
Hyatt Regency Chesapeake Bay
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.
A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.
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
₩259,622
₩322,715 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 fire pit surrounded by two white chairs with blue cushions, a small table, and potted plants.
A corner room with a window overlooking a green field, a wooden barrel, a chair, and a small table with a candle and flowers.

4. Marvel's on the Creek

Marvel's on the Creek
East New Market
₩270,798
₩300,586 total
includes taxes & fees
Oct 4 - Oct 5
Marvel's on the Creek
A modern living room with a large window overlooking the sea, a sofa, a fireplace, and a flat-screen TV mounted on the wall.
A modern living room with a large sofa, a coffee table, and a TV. There are large windows with a view of the water and a balcony.
A bedroom with a bed, a sofa, a TV, a fireplace, and a view of the sea.
A modern bathroom with a large bathtub, a white sink, and a view of the sea through large windows.

5. The Edge at Fager's Island

The Edge at Fager's Island
Midtown Ocean City
  • Seaside luxury awaits at this adults-only hotel, offering spectacular bay sunset views and indulgent jetted tubs in each intimate room.
₩370,598
₩415,070 total
includes taxes & fees
Nov 1 - Nov 2
The Edge at Fager's Island
A brick pathway leading to a pool area with a fence and potted plants.
A bedroom with a bed, a desk, a chair, a ceiling fan, and a patterned rug.
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 dining room with a large wooden table, matching chairs, a chandelier, and a patterned rug.

6. Cypress River Inn & Spa

Cypress River Inn & Spa
Snow Hill
₩291,000
₩325,920 total
includes taxes & fees
Oct 13 - Oct 14
Cypress River Inn & Spa
A waterfront property with a prominent building featuring a red roof and a tower, surrounded by water and marshland.
A spacious lobby with wooden ceiling, comfortable seating, large windows, and a fireplace.
A cozy living room with a fireplace, a chessboard, and a tray with snacks and drinks.
A restaurant with large windows offering a view of the sea. Tables are set with white tablecloths and wooden chairs.

7. Lighthouse Club Hotel

Lighthouse Club Hotel
Midtown Ocean City
  • Luxury coastal retreat with frette italian sheets, nightclub, and spa services near ocean city beach.
₩264,028
₩295,711 total
includes taxes & fees
Oct 12 - Oct 13
Lighthouse Club Hotel
A hot tub in a grassy area with a building in the background.
A pool with two Adirondack chairs and a basket of items on the grass.
A luxurious living room with a leather sofa, a vintage trunk, and a fireplace.
A room with a tufted armchair, a vase with white flowers, and a window with a view of the outdoors.

8. The Inn at Tacaro Estate

The Inn at Tacaro Estate
Tracys Landing
  • Indulge in beachside luxury at this 5-star estate featuring a seasonal outdoor pool, private balconies, and Italian Frette sheets.
₩474,894
₩541,384 total
includes taxes & fees
Nov 1 - Nov 2
The Inn at Tacaro Estate
A modern building with a bar area, outdoor seating, and a pool.
A modern dining area with a large table, chairs, and a view of a cityscape through large windows.
A marina with boats docked, a bridge, and buildings with illuminated windows.
A hotel lobby with a reflective floor, a reception desk, and a large floral arrangement.

9. 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.
₩576,938
₩677,903 total
includes taxes & fees
Nov 1 - Nov 2
Four Seasons Hotel Baltimore
A historic building with a prominent facade, large arched windows, and a central entrance.
A restaurant interior with brick walls, wooden tables, and hanging pendant lights.
A waterfront hotel with a pool, outdoor seating, and a view of the cityscape.
A modern outdoor seating area with a built-in fireplace, two grey sofas, and a round table with drinks.

10. Pendry Baltimore

Pendry Baltimore
Fells Point
  • Immerse in harbor-side luxury at Baltimore's Pendry hotel, where elegant relaxation meets waterfront sophistication.
₩566,078
₩720,976 total
includes taxes & fees
Nov 1 - Nov 2
Pendry Baltimore
View all properties

Top Eastern Shore Hotel Reviews

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 10 hours ago
Carousel Resort Hotel & Condominiums

Explore a world of travel with Expedia