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

5 Star Hotels in Eastern Shore, Maryland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Eastern Shore 5 Star Hotels

Tonight
18 Sept - 19 Sept
Tomorrow
19 Sept - 20 Sept
This weekend
18 Sept - 20 Sept
Next weekend
25 Sept - 27 Sept

Our top choices for Eastern Shore 5-star hotels

Premium bedding, down duvets, in-room safe, desk
Golf
Outdoor pool
Premium bedding, down duvets, in-room safe, desk

1. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
United States
Andrew
€578
includes taxes & fees
13 Oct - 14 Oct
Inn at Perry Cabin
Exterior
Dining
Deluxe Cottage, Balcony, River View
Exterior

2. Cypress River Inn & Spa

Cypress River Inn & Spa
Snow Hill
United States
Hans
€210
includes taxes & fees
29 Sept - 30 Sept
Cypress River Inn & Spa
Save an average of 15% on thousands of hotels when you're signed in

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
€263
29 Sept - 30 Sept
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Hyatt Regency Chesapeake Bay
Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites

3200 N Baltimore Ave Ocean City MD
€148
18 Oct - 19 Oct
includes taxes & fees
8.8/10 Excellent! (1,363 reviews)
Hilton Ocean City Oceanfront Suites
DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront

3301 Atlantic Ave Ocean City MD
€95
18 Oct - 19 Oct
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
DoubleTree by Hilton Ocean City Oceanfront
Still don't see what you're looking for?
See all properties in Eastern Shore.
You can also use these popular filters to refine your search.
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

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 €95
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.

Explore a world of travel with Expedia