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

5 Stars Hotels in Eastern Shore, Maryland from CA $438

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Check availability on Eastern Shore 5 Star Hotels

This weekend
Jul 3 - Jul 5
Next weekend
Jul 10 - Jul 12

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 CA $1,042
CA $1,146 total
includes taxes & fees
Aug 2 - Aug 3
Inn at Perry Cabin
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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 CA $425 per night from Jul 6 to Jul 7
CA $425
CA $550 total
Jul 6 - Jul 7
includes taxes & fees
8.8/10 Excellent! (1,001 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 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

Find out more about Eastern Shore

Five Star Hotels in Eastern Shore

There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Eastern Shore so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Eastern Shore and get ready to be pampered like never before.

Get a Great Deal on 5-Star Hotels in Eastern Shore

Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places.

Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town.

Make Your Escape to Eastern Shore

The results are in, and Eastern Shore 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Eastern Shore! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Eastern Shore today and settle down in the lap of luxury tomorrow.

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 depends on factors such as when you plan to go and the length of your escape. Our insider tip for scoring an awesome deal? Use our pricing filters to compare all of the available accommodations for your selected dates.

  • Search for the lowest price per night from CA $438

What makes a hotel 5 stars in Eastern Shore?
Faultless guest service is the hallmark of every 5-star hotel in Eastern Shore. From the second you arrive, staff attend to your every whim, whether arranging customized tours or providing in-room massages. Additionally, hotels have to offer upscale conveniences to be entitled to a 5-star rating. These can include luxury toiletries, spas or saunas, swimming pools, gourmet kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Eastern Shore?
Find an indulgent stay that includes your lodging, meals, bar and entertainment in Eastern Shore with our handy filter tool. Search for resorts rated 5 stars and select the "All inclusive" filter. Double-check what's included in the upfront price. That way, you'll be ready to maximize all the perks on offer from the moment you step into the lobby.

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