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

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Check availability on Eastern Shore 5 Star Hotels

Tonight
2 Sept - 3 Sept
Tomorrow
3 Sept - 4 Sept
This weekend
4 Sept - 6 Sept
Next weekend
11 Sept - 13 Sept

Our top choices for Eastern Shore 5-star hotels

Premium bedding, down duvets, in-room safe, desk
Premium bedding, down duvets, in-room safe, desk
Suite, 1 Bedroom (Water View) | Premium bedding, down duvets, in-room safe, desk
Golf

1. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
United States
John
£527
includes taxes & fees
16 Sept - 17 Sept
Inn at Perry Cabin
Exterior
Deluxe Cottage, Balcony, River View | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds
Exterior
Dining

2. Cypress River Inn & Spa

Cypress River Inn & Spa
Snow Hill
United States
Hans
£171
includes taxes & fees
3 Sept - 4 Sept
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
£227
8 Sept - 9 Sept
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
£147
8 Sept - 9 Sept
includes taxes & fees
DoubleTree by Hilton Ocean City Oceanfront
Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites

3200 N Baltimore Ave Ocean City MD
£170
30 Sept - 1 Oct
includes taxes & fees
8.8/10 Excellent! (1,368 reviews)
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 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
A marina with numerous boats docked at wooden piers under a clear sky.

Top Eastern Shore Hotel Reviews

Find out more about Eastern Shore

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Eastern Shore?
The amount you pay for a 5-star hotel in Eastern Shore depends on factors such as when you plan to travel and the length of your getaway. Our top tip for landing an awesome deal? Use our pricing filters to check out the available options for your preferred dates.
  • Search for the lowest price per night from £147
What makes a hotel 5 stars in Eastern Shore?
From high-end restaurants and fitness centres to swimming pools and premium bedding, the 5-star experience in Eastern Shore is all about comfort and luxury. But it calls for more than just upscale perks to earn a 5-star rating. Hotels must also offer superb guest-centric services like massage treatments, laundry and dry cleaning and 24-hour room service.
Are there any 5-star all-inclusive resorts in Eastern Shore?
Use our filter tool to find a luxury escape in Eastern Shore where everything you need is included in the price. After your initial search, refine your results for hotels that have a 5-star rating and are categorised as "All inclusive." The main thing on the itinerary at these stays? Pure indulgence and relaxation.

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