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

Eastern Shore 5 Stars Hotels

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Check availability on Eastern Shore 5 Star Hotels

Tonight
Oct 6 - Oct 7
Tomorrow
Oct 7 - Oct 8
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Eastern Shore 5-star hotels

1. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
United States
Virgilio
₩687,595
₩756,354 total
includes taxes & fees
Nov 3 - Nov 4
Inn at Perry Cabin

2. Cypress River Inn & Spa

Cypress River Inn & Spa
Snow Hill
United States
Hans
₩288,066
₩322,634 total
includes taxes & fees
Oct 14 - Oct 15
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
₩256,227
₩329,131 total
Nov 4 - Nov 5
includes taxes & fees
Hyatt Regency Chesapeake Bay
DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront

3301 Atlantic Ave Ocean City MD
₩119,800
₩134,176 total
Nov 1 - Nov 2
includes taxes & fees
9/10 Wonderful! (1,007 reviews)
DoubleTree by Hilton Ocean City Oceanfront
Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites

3200 N Baltimore Ave Ocean City MD
₩148,376
₩166,180 total
Nov 3 - Nov 4
includes taxes & fees
Hilton Ocean City Oceanfront Suites
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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.

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A historic white mansion with a sign in front.

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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 accommodations 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 ₩134,176
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 vacation is absolute indulgence from the moment you step foot in the lobby.

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