Explore top 2026 5 Star Hotels in Eastern Shore

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Top Eastern Shore 5 Star hotels

Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln St. Michaels MD
$670 nightly
The price is $737 total per night from Oct 6 to Oct 7
$737 total
Oct 6 - Oct 7
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! (399 reviews)
"All staff were very pleasant, engaged, and helpful. Everyone seems to genuinely care about making the experience memorable. The property, setting, grounds, and amenities are beautiful and well-maintained."

Reviewed on Aug 31, 2026

Opens in a new windowInn at Perry Cabin
Cypress River Inn & Spa

Cypress River Inn & Spa

5 out of 5
201 E Market St Snow Hill MD
$229 nightly
The price is $257 total per night from Sep 7 to Sep 8
$257 total
Sep 7 - Sep 8
Total with taxes and fees
A restaurant, free self parking, and a garden are among this bed & breakfast's amenities. WiFi in public areas is free. A snack bar/deli, a communal living room, ...
Opens in a new windowCypress River Inn & Spa
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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.

Recent Eastern Shore hotel reviews by fellow wanderers

Howard Johnson by Wyndham Ocean City Oceanfront

Howard Johnson by Wyndham Ocean City Oceanfront

4 out of 5
Posted 4 hours ago
Travelocity Verified Review
"Overall, a positive experience. However, this is an older property without sound protection between floors or walls. Therefore, you could possibly hear footsteps above you on a lower floor. Or a louder neighbor or their pet. Next time, I would book the top floor and request the end."
A verified traveler stayed at Howard Johnson by Wyndham Ocean City Oceanfront
Howard Johnson by Wyndham Ocean City Oceanfront

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