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

Find 5 Star Hotels in Eastern Shore, MD from AED 705

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Check availability on Eastern Shore 5 Star Hotels

Tonight
29 Aug - 30 Aug
Tomorrow
30 Aug - 31 Aug
Next weekend
4 Sep - 6 Sep
In two weeks
11 Sep - 13 Sep

Our top choices for Eastern Shore 5-star hotels

Premium bedding, down comforters, in-room safe, desk
Golf
Outdoor pool
Suite, 1 Bedroom (Water View) | Premium bedding, down comforters, in-room safe, desk

1. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
AED 1,772
AED 1,949 total
includes taxes & fees
23 Sep - 24 Sep
Inn at Perry Cabin
Exterior
Dining
Luxury Cottage, Garden View | Living area | 55-inch Smart TV with cable channels, Netflix, Hulu
Exterior

2. Cypress River Inn & Spa

Cypress River Inn & Spa
Snow Hill
United States
Hans
AED 734
AED 822 total
includes taxes & fees
3 Sep - 4 Sep
Cypress River Inn & Spa
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Eastern Shore.
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

100 Heron Blvd Cambridge MD
AED 801
AED 1,084 total
29 Sep - 30 Sep
includes taxes & fees
Hyatt Regency Chesapeake Bay
DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront

3301 Atlantic Ave Ocean City MD
AED 629
AED 705 total
7 Sep - 8 Sep
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
DoubleTree by Hilton Ocean City Oceanfront
Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites

3200 N Baltimore Ave Ocean City MD
AED 828
AED 928 total
20 Sep - 21 Sep
includes taxes & fees
8.8/10 Excellent! (1,374 reviews)
Hilton Ocean City Oceanfront Suites
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Learn more about Eastern Shore

Charming coastal towns and pristine beaches dot the Chesapeake Bay's eastern shoreline, inviting you to explore maritime history and savor fresh seafood. Kayak through serene marshlands, visit Assateague Island's wild ponies, or take a scenic drive to discover quaint antique shops and waterfront restaurants.

See all hotels in Eastern Shore
A marina with numerous boats docked at wooden piers under a clear sky.

Top Eastern Shore Hotel Reviews

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Eastern Shore?
How much you pay for a 5-star hotel in Eastern Shore can vary based on when you want to travel and how long you plan to stay, among several factors. Use our price per night filter and other search tools to score the best rate on a plush stay.
  • Search for the lowest price per night from AED 705
What makes a hotel 5 stars in Eastern Shore?
From high-end dining venues and all-day fitness centers to pools and superior bedding, the 5-star experience in Eastern Shore is all about luxury and comfort. But it calls for more than just upscale perks to earn a 5-star rating. Hotels must also provide outstanding guest services like in-room massages, laundry and dry cleaning and 24-hour room service.
Are there any 5-star all-inclusive resorts in Eastern Shore?
Use our handy filters to find an upscale getaway in Eastern Shore where most of what you need is included. After your initial search, narrow your results for hotels that have a rating of 5 stars and are categorized as "All inclusive." The most important thing on the itinerary at these stays? Relaxation and indulgence.

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