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 18 - Oct 19
Tomorrow
Oct 19 - Oct 20
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Our top choices for Eastern Shore 5-star hotels

A room with a view of a wooden deck and a gazebo by the water.
A golf course with a water hazard and surrounding trees.
A living room with a fireplace, a sofa, a coffee table, and a television mounted on the wall.
A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.

1. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
United States
Virgilio
NT$15,905
NT$17,496 total
includes taxes & fees
Nov 18 - Nov 19
Inn at Perry Cabin
A brick pathway leading to a pool area with a fence and potted plants.
A living room with a flat-screen TV on a wooden cabinet, a coffee machine on a shelf, and a door leading to another room.
A two-story house with a balcony, a covered porch, and a brick chimney.
A bedroom with a bed, a desk, a chair, a ceiling fan, and a patterned rug.

2. Cypress River Inn & Spa

Cypress River Inn & Spa
Snow Hill
United States
Hans
NT$6,964
NT$7,799 total
includes taxes & fees
Oct 19 - Oct 20
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
NT$5,022
NT$6,626 total
Nov 18 - Nov 19
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
NT$2,630
NT$2,946 total
Nov 1 - Nov 2
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
DoubleTree by Hilton Ocean City Oceanfront
Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites

3200 N Baltimore Ave Ocean City MD
NT$3,718
NT$4,164 total
Nov 1 - Nov 2
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.

See all hotels in Eastern Shore
A historic white mansion with a sign in front.

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 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 NT$2,946
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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