Explore top 2026 5 Star Hotels in Eastern Shore

Name: Inn at Perry Cabin
Price range: $699 total
Rating: 9.6

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Top Eastern Shore 5 Star hotels

Inn at Perry Cabin

308 Watkins Ln St. Michaels MD

$635 nightly

$699 total

Aug 2 - Aug 3

Total with taxes and fees

This luxury hotel features a golf course, a full-service spa, and a marina. Families will appreciate complimentary bicycles, kid-friendly dining, and in-room ...

9.6/10 Exceptional! (393 reviews)

"Beautiful property, very well maintained. Dinner and Brunch at Stars were both very good. We loved being by the boats. Staff was accommodating when I had to do a zoom call on the morning of departure and found me a quiet private spot. Short walk to the Maritime Museum which was worth going to learn ..."

Reviewed on Jul 21, 2026

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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.

Eastern Shore Resorts & 5 Star Hotels

Looking for your own little slice of heaven during your next trip? Check out all the best 5-star hotels in Eastern Shore to make sure your trip is as extravagantly comfortable as you expect.

Whether you plan on staying in your room the whole time or getting out and enjoying the city, you’ll be living the life while staying at your luxury accommodation. With so many amenities at your beck and call, you might try to turn your stay into a staycation!

Many of the 5-star hotels have award-winning restaurants you can dine at, as well as plush bedding and a concierge service to take care of your every need. Most also offer pools and modern fitness centers, not to mention high-speed Wi-Fi.

For your next trip, book a hotel that can be your own little hideaway, whether you’re in town for business or leisure. Eastern Shore 5-star hotels provide you with all the comforts and amenities you expect from a sophisticated hotel, with a staff that’s happy to ensure you have everything you need to feel at home.

Whether you’re a first-time guest, or you’ve stayed in 5-star hotels in Eastern Shore before, you’ll have no shortage of options to choose from on your next trip when you book with Travelocity. Browse our vast selection and find great deals on luxury lodging.