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

Find 5 Star Hotels in Eastern Shore, MD from AED 472

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Our top choices for Eastern Shore 5-star hotels

A room with a fireplace, a dining area with chairs, a large window with a view of the outside, and a cabinet with bottles.

1. Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (407 reviews)
"Fantastic place; one of those that you don’t want to leave the property until the very sad time to go. Lovely staff, all of them, amazing food."
United States
Virgilio
The price is AED 1,599
AED 1,759 total
includes taxes & fees
9 Dec - 10 Dec
Inn at Perry Cabin
A brick pathway leading to a pool area with a fence and potted plants.

2. Cypress River Inn & Spa

Cypress River Inn & Spa
5.0 star property
Snow Hill
8.6 out of 10, Excellent, (8 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 AED 687
AED 769 total
includes taxes & fees
12 Nov - 13 Nov
Cypress River Inn & Spa
Exterior

3. Inn at 202 Dover

Inn at 202 Dover
5.0 star property
Easton
10.0 out of 10, Exceptional, (14 reviews)
"Celebrated our 33rd anniversary here and enjoyed it thoroughly. Felt pampered and welcomed. Best B&B ever! Everything from the room to the food was exceptional. Every need was anticipated and met. Looking forward to our next visit. The quintessential "living like a king" experience."
United States
James
Inn at 202 Dover
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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.
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

180 Pier One Road Stevensville MD
The price is AED 665 per night from Dec 9 to Dec 10
AED 665
AED 832 total
9 Dec - 10 Dec
includes taxes & fees
9.4/10 Exceptional! (513 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.

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A historic white mansion with a sign in front.

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 472

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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