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

Find 5 Star Hotels in Eastern Shore, MD from SAR 850

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Check availability on Eastern Shore 5 Star Hotels

Next weekend
7 Aug - 9 Aug
In two weeks
14 Aug - 16 Aug

Our top choices for Eastern Shore 5-star hotels

Premium bedding, down comforters, in-room safe, desk

1. Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (395 reviews)
"maybe a little overpriced but a great place to stay in St Michaels!"
United States
Michel
The price is SAR 2,254
SAR 2,480 total
includes taxes & fees
2 Sep - 3 Sep
Inn at Perry Cabin
Exterior

2. Cypress River Inn & Spa

Cypress River Inn & Spa
5.0 star property
Snow Hill
9.0 out of 10, Wonderful, (4 reviews)
"I fell in love with the charm of this Inn, I can't wait for the restaurant to be up and running so I can come back and stay."
United States
Hans
The price is SAR 759
SAR 850 total
includes taxes & fees
2 Sep - 3 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
The price is SAR 838 per night from Aug 26 to Aug 27
SAR 838
SAR 1,130 total
26 Aug - 27 Aug
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
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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 SAR 1,130

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.