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
Oct 11 - Oct 12
Tomorrow
Oct 12 - Oct 13
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 living room with a fireplace, a sofa, a coffee table, and a television mounted on the wall.
A golf course with a water hazard and surrounding trees.
A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.

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 dining area with round tables, high ceilings with ductwork, and a stone fireplace.
A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.

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 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 high ceilings, large windows, and modern chandeliers.

3. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
  • Chesapeake Bay resort offers luxury with private beach, full-service spa, and championship golf.
₩246,608
₩318,177 total
includes taxes & fees
Nov 8 - Nov 9
Hyatt Regency Chesapeake Bay
A wooden dock with a bench and a wooden post with a light fixture.
A fire pit surrounded by two white chairs with blue cushions, a small table, and potted plants.
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.

4. Marvel's on the Creek

Marvel's on the Creek
East New Market
₩268,052
₩297,537 total
includes taxes & fees
Oct 13 - Oct 14
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 modern bathroom with a large bathtub, a white sink, and a view of the sea through large windows.
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 restaurant with large windows offering a view of the sea. Tables are set with white tablecloths and wooden chairs.
A spacious lobby with wooden ceiling, comfortable seating, large windows, and a fireplace.
A rocking chair on a wooden deck with a view of the ocean and a sunset.

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
Nov 8 - Nov 9
Lighthouse Club Hotel
A brick pathway leading to a pool area with a fence and potted plants.
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.
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.

7. Cypress River Inn & Spa

Cypress River Inn & Spa
Snow Hill
₩288,049
₩322,615 total
includes taxes & fees
Oct 13 - Oct 14
Cypress River Inn & Spa
A hot tub in a grassy area with a building in the background.
A room with a tufted armchair, a vase with white flowers, and a window with a view of the outdoors.
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.

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 hotel lobby with a reflective floor, a reception desk, and a large floral arrangement.
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.

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 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.
A modern lounge area with round tables, cushioned chairs, and a large floral painting on the wall.

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

Plim Plaza Hotel

Plim Plaza Hotel

10/10 Excellent
"I checked out a day early because of storm coming. I put everything away and then I had to call down the next day to see if I'd left a pair of gray shorts in the room. They did find a pair of gray shorts in the room but also tried to say the room smelled very badly of smoke and I never smoked in that room. So I'd watch yourself because who knows if somebody went in there after I checked out one of the employees and then was smoking in that room and trying to blame me"
Ruby 3-night trip
Posted 1 hour ago
Plim Plaza Hotel
Quality Inn Oceanfront

Quality Inn Oceanfront

10/10 Excellent
"loved the courtyard with all the plants, the pool and hot tubs, the birds, the bar area. the bartenders were very friendly and informative"
yvonne 3-night trip
Posted 3 hours ago
Quality Inn Oceanfront
St Michaels Inn

St Michaels Inn

10/10 Excellent
"na"
Jeffrey 2-night trip
Posted 3 hours ago
St Michaels Inn
Princess Bayside Beach Hotel

Princess Bayside Beach Hotel

8/10 Good
"Beautiful view"
Ellen 3-night trip
Posted 8 hours ago
Princess Bayside Beach Hotel
Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel

Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel

10/10 Excellent
"Was a pleasant stay would stay again or recommend to others"
Les 1-night trip
Posted 10 hours ago
Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel

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