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 29 - Sep 30
Tomorrow
Sep 30 - Oct 1
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 golf course with a water hazard and surrounding trees.
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.

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.
₩696,937
₩766,630 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 large building with a tower in the background, and a dock extending into the water.
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.
₩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 spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
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
₩259,823
₩322,965 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 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.
A sunlit room with a checkered sofa, wicker chairs, a glass table, and large windows offering a view of greenery.

4. Marvel's on the Creek

Marvel's on the Creek
East New Market
₩270,814
₩300,603 total
includes taxes & fees
Sep 30 - Oct 1
Marvel's on the Creek
A resort pool area with lounge chairs, palm trees, and a boat-shaped water feature.
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.
A dining table set with wine glasses, a bottle of Riesling wine, a vase with flowers, and a basket of bread.
An aerial view of a coastal city with a beachfront hotel featuring multiple floors, a swimming pool, and a marina 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 27 - Oct 28
Hilton Ocean City Oceanfront Suites
A balcony with wicker furniture and a table, overlooking a beach with umbrellas and people.
A swimming pool with lounge chairs and umbrellas, surrounded by large windows and a glass ceiling.
A beachfront hotel with multiple floors and balconies, a sandy beach in the foreground, and a clear sky.
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
₩132,095
₩147,945 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 banquet hall with round tables set for dining, large windows with a view of a lake, and white chairs.
A wooden console table with framed floral artwork, two lamps, and two ottomans.
A deck with wicker furniture, a table, and an umbrella, overlooking a lake with trees and a dock.

7. The Oaks Waterfront

The Oaks Waterfront
Easton
₩595,926
₩655,519 total
includes taxes & fees
Oct 1 - Oct 2
The Oaks Waterfront
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 two-story house with a balcony, a covered porch, and a brick chimney.
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 30 - Oct 1
Cypress River Inn & Spa
A courtyard with a brick building, potted plants, and a well-lit outdoor area.
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.
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 8 - Oct 9
The Ivy Hotel
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 spa room with cushioned seating, a glass door leading outside, and a ceiling light fixture.
A marina with boats docked, a bridge, and buildings with illuminated windows.

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 11 - Oct 12
Four Seasons Hotel Baltimore
View all properties

Top Eastern Shore Hotel Reviews

Castle in the Sand

Castle in the Sand

10/10 Excellent
"Nice front desk guy. Typical OC room but clean"
Mike 2-night trip
Posted 5 hours ago
Castle in the Sand
Plim Plaza Hotel

Plim Plaza Hotel

10/10 Excellent
"We had an absolute blast staying here. The staff and the other guests were great! We were there for the Nor’Easter and although the Oceans Calling Festival was cancelled and the weather was awful we still had fun. We did cut our stay short due to deteriorating weather conditions, but booked for next year before we left. If you want a clean place to stay and want to be surrounded by all the OC Boardwalk has to offer, look no further. Yes, the rooms are small but what are you doing in your room? Go outside, hang out on the porch or the huge lobby. So much fun."
Lori 4-night trip
Posted 14 hours ago
Plim Plaza Hotel
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 1 day ago
Quality Inn Oceanfront

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