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

Find 5 Star Hotels in Eastern Shore, MD from $256

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Check availability on Eastern Shore 5 Star Hotels

Next weekend
Jul 31 - Aug 2
In two weeks
Aug 7 - Aug 9

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, (395 reviews)
"maybe a little overpriced but a great place to stay in St Michaels!"
United States
Michel
$635 nightly
The price is $699
Aug 2 - Aug 3
Total with taxes and fees
Inn at Perry Cabin
Exterior

Cypress River Inn & Spa

Cypress River Inn & Spa
5.0 star property
Snow Hill
8.8 out of 10, Excellent, (3 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
$229 nightly
The price is $256
Jul 27 - Jul 28
Total with taxes and fees
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
$296 nightly
The price is $336 total per night from Aug 18 to Aug 19
$336 total
Aug 18 - Aug 19
Total with taxes and fees
8.8/10 Excellent! (1,004 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

Find out more about Eastern Shore

You enjoy the finer things in life, both at home and on vacation. Add further luxury on your next trip to Eastern Shore by treating yourself to the best of the best when it comes to accommodation. It's an ideal pairing. There's no reason to delay a getaway to Eastern Shore any longer. You'll join the multitudes of vacationers who have made Eastern Shore so fashionable in the last year. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Don't wait any longer. Reserve one of our 5-star hotels in Eastern Shore and indulge in the finer things in life for a while.

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

You'll have a fantastic time at one of these 5-star hotels. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. You're sure to find exactly the accommodation you need. You can also expect excellent customer service from these hotels, so get ready for a wonderful adventure. How do you want to relax? A mud wrap treatment that will leave you feeling outstanding? 24-hour room service, so you can order that berry tart in the wee hours of the morning? A deep-tissue massage to help your cares fall away?

Can't wait to get outside? We hear you. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what you end up doing, the 5-star hotels in Eastern Shore are the perfect place to relax after an exciting day. Ready to learn more? Then check out our listings and pick the perfect accommodation for your needs.

Your Getaway Starts Today

Numerous visitors make Eastern Shore the place to vacation. Why not join their ranks? If you've been dreaming about a vacation set here, then go ahead and book it. A surge in interest means these great hotel rooms will go quickly. It's time to plan your next great escape. Opt for one of our Eastern Shore 5-star hotels today and decompress in total tranquility 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 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 $336

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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