5 Star Hotels in Eastern Shore, Maryland

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Check availability on Eastern Shore 5 Star Hotels

Tonight
20 Dec - 21 Dec
Tomorrow
21 Dec - 22 Dec
Next weekend
26 Dec - 28 Dec
In two weeks
2 Jan - 4 Jan

Our top choices for Eastern Shore 5-star hotels

Breakfast, lunch, dinner served; sea views
Inn at Perry Cabin

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (371)
"Friendly and attentive staff, good cleaning services"
United States
Nathan
The price is €539
includes taxes & fees
23 Dec - 24 Dec
Inn at Perry Cabin
Dinner served
Inn at 202 Dover

Inn at 202 Dover

Inn at 202 Dover
5.0 star property
Easton
10.0 out of 10, Exceptional, (14)
"Celebrated our 33rd anniversary here and enjoyed it thoroughly. Felt pampered and welcomed. Best B&B ever! Everything from the room to the food was exceptional. Every need was anticipated and met. Looking forward to our next visit. The quintessential "living like a king" experience."
United States
James
Inn at 202 Dover
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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.
Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites

3200 N Baltimore Ave Ocean City MD
The price is €102 per night from 4 Jan to 5 Jan
€102
4 Jan - 5 Jan 2026
includes taxes & fees
8.8/10 Excellent! (1,344 reviews)
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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
Long Wharf Park

Top Eastern Shore Hotel Reviews

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Eastern Shore?
You'll find several pricing options for a 5-star hotel in Eastern Shore on Expedia. The amount you pay will depend on when you want to travel, length of stay and other factors. Compare all of the available accommodation for your preferred dates and use our pricing and other filters to find the ideal luxury stay.

  • Search for the lowest price per night from €80

What makes a hotel 5 stars in Eastern Shore?
From gourmet restaurants and all-day gyms to pools and superior bedding, the 5-star experience in Eastern Shore is all about comfort and luxury. But it requires more than just upscale perks to earn a 5-star rating. Stays must also offer exceptional guest-centric services like in-room massage treatments, on-site dry cleaning and laundry and 24-hour concierge services.
Are there any 5-star all-inclusive resorts in Eastern Shore?
Expedia's filters are the best way to narrow down what you want. Select "All inclusive" and "5-star" to show the most luxurious hotels in Eastern Shore where your meals, lodging, activities and entertainment are included in the upfront price. At these stays, your holiday is absolute indulgence from the moment you step foot in the lobby.

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