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

Eastern Shore Hotel Guide - 5 Stars Hotels in Eastern Shore, Maryland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Eastern Shore 5 Star Hotels

This weekend
10 Jul - 12 Jul
Next weekend
17 Jul - 19 Jul

Our top choices for Eastern Shore 5-star hotels

Breakfast, lunch, dinner and brunch served

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (391 reviews)
"maybe a little overpriced but a great place to stay in St Michaels!"
United States
Michel
The price is Rp11.963.358
Rp13.159.693 total
includes taxes & fees
23 Jul - 24 Jul
Inn at Perry Cabin
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 Rp5.029.640 per night from 5 Aug to 6 Aug
Rp5.029.640
Rp6.565.477 total
5 Aug - 6 Aug
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
Still don't see what you're looking for?
See all properties in Eastern Shore.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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 savour 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?
The amount you pay for a 5-star hotel in Eastern Shore depends on factors such as when you plan to travel and the length of your getaway. Our top tip for landing an awesome deal? Use our pricing filters to check out the available options for your preferred dates.

  • Search for the lowest price per night from Rp4.808.335

What makes a hotel 5 stars in Eastern Shore?
From high-end restaurants and fitness centres to swimming pools and premium bedding, the 5-star experience in Eastern Shore is all about comfort and luxury. But it calls for more than just upscale perks to earn a 5-star rating. Hotels must also offer superb guest-centric services like massage treatments, laundry and dry cleaning and 24-hour room service.
Are there any 5-star all-inclusive resorts in Eastern Shore?
Use our filter tool to find a luxury escape in Eastern Shore where everything you need is included in the price. After your initial search, refine your results for hotels that have a 5-star rating and are categorised as "All inclusive." The main thing on the itinerary at these stays? Pure indulgence and relaxation.