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 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 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.

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 marina with boats docked, a sandy beach, and a clear blue sky.
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.

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 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.
A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.

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 sunlit room with a checkered sofa, wicker chairs, a glass table, and large windows offering a view of greenery.
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 wooden dock leading to a house with a lawn and a pond.

4. Marvel's on the Creek

Marvel's on the Creek
East New Market
₩271,500
₩301,366 total
includes taxes & fees
Oct 2 - Oct 3
Marvel's on the Creek
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 two-story house with a balcony, a covered porch, and a brick chimney.

5. 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 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.
₩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 cozy room with a brick fireplace, leather armchairs, and a rustic wooden table.
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.

7. 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.

8. 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 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 restaurant interior with brick walls, wooden tables, and hanging pendant lights.

9. 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
A courtyard with a brick building, potted plants, and a well-lit outdoor area.
A lobby with a red carpet, two sofas with cushions, a large plant, and a fireplace.
A building with large windows, outdoor seating, and a staircase.
A luxurious lobby with a high ceiling, ornate chandeliers, plush seating, and a large plant.

10. The Ivy Hotel

The Ivy Hotel
Midtown
  • Indulgent Baltimore retreat offering historic charm, a full-service spa, and fine dining.
₩971,292
₩1,141,269 total
includes taxes & fees
Oct 7 - Oct 8
The Ivy Hotel
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Top Eastern Shore Hotel Reviews

Castle in the Sand

Castle in the Sand

8/10 Good
"The beach view was amazing although the balcony is only made for 2 people to use at a time. Although the ac unit is necessary, it was loud and hot when sitting on the balcony with the little space available on the balcony for the 2 chairs and one small table. Try the breakfast buffet and go Hungry! You will not regret it, and you definitely get your monies worth! The rooms are cozy. It is not new or boujee, but it is clean and nothing major to complain about. Coconuts bar was nice and the happy hour special is two for one drinks!! WIN!! Guests of Hotel get in at 4:45 and you get to beat the outsiders for seats and drinks :) We were there for our 24th wedding anniversary during the 2026 Nor' Eastern and made the best of it! We will be back!"
Lawrence 4-night trip
Posted 1 hour ago
Castle in the Sand
Crystal Beach Hotel

Crystal Beach Hotel

10/10 Excellent
"Everything was great, front desk was very helpful"
Hilda 1-night trip
Posted 6 hours ago
Crystal Beach Hotel
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 21 hours ago
Carousel Resort Hotel & Condominiums

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