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 10 - Oct 11
Tomorrow
Oct 11 - Oct 12
Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25

Our top choices for Eastern Shore luxury hotels

A room with a view of a wooden deck and a gazebo by the water.
A golf course with a water hazard and surrounding trees.
A hotel room with a large bed, a chair, a desk, and a television.
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.
₩687,553
₩756,308 total
includes taxes & fees
Nov 8 - Nov 9
Inn at Perry Cabin
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 spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.

2. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
₩273,413
₩337,585 total
includes taxes & fees
Nov 2 - Nov 3
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 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.
A marina with boats docked, a large building with a tower in the background, and a dock extending into the water.

3. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
  • Chesapeake Bay resort offers luxury with private beach, full-service spa, and championship golf.
₩239,907
₩310,572 total
includes taxes & fees
Nov 9 - Nov 10
Hyatt Regency Chesapeake Bay
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
₩268,052
₩297,537 total
includes taxes & fees
Oct 11 - Oct 12
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 bathroom with a large bathtub, a white sink, and a view of the sea through large windows.
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 spacious room with a large window overlooking a body of water, a built-in fireplace, and a cozy seating area.

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.
₩365,891
₩409,798 total
includes taxes & fees
Nov 1 - Nov 2
The Edge at Fager's Island
A waterfront property with a prominent building featuring a red roof and a tower, surrounded by water and marshland.
A cozy living room with a fireplace, a chessboard, and a tray with snacks and drinks.
A rocking chair on a wooden deck with a view of the ocean and a sunset.
A restaurant with large windows offering a view of the sea. Tables are set with white tablecloths and wooden chairs.

6. Lighthouse Club Hotel

Lighthouse Club Hotel
Midtown Ocean City
  • Luxury coastal retreat with frette italian sheets, nightclub, and spa services near ocean city beach.
₩261,351
₩292,713 total
includes taxes & fees
Oct 12 - Oct 13
Lighthouse Club Hotel
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 two-story house with a balcony, a covered porch, and a brick chimney.
A bedroom with a bed, a desk, a chair, a ceiling fan, and a patterned rug.

7. Cypress River Inn & Spa

Cypress River Inn & Spa
Snow Hill
₩288,049
₩322,615 total
includes taxes & fees
Oct 12 - Oct 13
Cypress River Inn & Spa
A hot tub in a grassy area with a building in the background.
A luxurious living room with a leather sofa, a vintage trunk, and a fireplace.
A pool with two Adirondack chairs and a basket of items on the grass.
A cozy room with a brick fireplace, leather armchairs, and a rustic wooden table.

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.
₩468,863
₩534,509 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 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.

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.
₩569,611
₩669,292 total
includes taxes & fees
Nov 10 - Nov 11
Four Seasons Hotel Baltimore
A historic building with a prominent facade, large arched windows, and a central entrance.
A modern lounge area with round tables, cushioned chairs, and a large floral painting on the wall.
A modern outdoor seating area with a built-in fireplace, two grey sofas, and a round table with drinks.
A waterfront hotel with a pool, outdoor seating, and a view of the cityscape.

10. Pendry Baltimore

Pendry Baltimore
Fells Point
  • Immerse in harbor-side luxury at Baltimore's Pendry hotel, where elegant relaxation meets waterfront sophistication.
₩474,452
₩612,606 total
includes taxes & fees
Nov 10 - Nov 11
Pendry Baltimore
View all properties

Top Eastern Shore Hotel Reviews

St Michaels Inn

St Michaels Inn

10/10 Excellent
"We travel to St micheals md, several times a year, during the oyster season. Usually we stay at hotels in easton, so this time we tried the st micheals inn. It's closer to the Cheasapeake Landing restaurant. We were placed in a room opposite the main street, which made for a very quiet evening. Much better than those hotels off rt.50. The breakfast was a "hot" breakfast and included with the stay. The beds are comfortable, and the showers hot and forceful."
William 1-night trip
Posted 1 hour ago
St Michaels Inn
Fenwick Inn

Fenwick Inn

8/10 Good
"Nice clean hotel... I would definitely stay there again"
Keith 2-night trip
Posted 6 hours ago
Fenwick Inn

Explore a world of travel with Expedia