A waterfront street lined with trees and a white building with a balcony.

5 Star Hotels in St. Michaels, Maryland

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Check availability on St. Michaels 5 Star Hotels

Tonight
26 Aug - 27 Aug
Tomorrow
27 Aug - 28 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

Our top choices for St. Michaels 5-star hotels

Room
Golf
Suite, 1 Bedroom (Water View)
Room

1. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
United States
Andrew
€419
includes taxes & fees
7 Sept - 8 Sept
Inn at Perry Cabin
Pool
Luxury Suite, 1 Bedroom
Room
Interior

2. The Inn at Tacaro Estate

The Inn at Tacaro Estate
Tracys Landing
United States
James
€387
includes taxes & fees
2 Sept - 3 Sept
The Inn at Tacaro Estate
Restaurant
Room
Interior
Exterior

3. Inn at 202 Dover

Inn at 202 Dover
Easton
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 St. Michaels.
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD
€95
30 Aug - 31 Aug
includes taxes & fees
DoubleTree by Hilton Hotel Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

126 West St Annapolis MD
€152
30 Aug - 31 Aug
includes taxes & fees
9.4/10 Exceptional! (1,028 reviews)
Graduate by Hilton Annapolis
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

80 Compromise St Annapolis MD
€210
13 Sept - 14 Sept
includes taxes & fees
8.8/10 Excellent! (981 reviews)
Annapolis Waterfront Hotel, Autograph Collection
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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 St. Michaels

Stroll down charming streets lined with boutiques and seafood restaurants in this quaint Chesapeake Bay town. Sail on a skipjack, visit the maritime museum, or bike to nearby wineries for a taste of Eastern Shore living.

See all hotels in St. Michaels
A lighthouse at sunset with a boat docked nearby.

Top St. Michaels Hotel Reviews

Frequently asked questions

What are the best 5-star hotels in St. Michaels?
Treat yourself to a stay at Inn at Perry Cabin. This is one of the most popular 5-star hotels in St. Michaels based on Expedia guest reviews. From its guest services to its well-appointed rooms and prime location, you can rely on an exceptional guest experience.
How much does it cost to stay in a 5-star hotel in St. Michaels?
You'll find many different pricing options for a 5-star hotel in St. Michaels on Expedia. How much you'll pay will depend on when you plan to travel, trip length and other factors. Compare all of the available accommodation for your preferred dates and use our pricing and other filters to lock in the ideal luxury stay.
  • Search for the lowest price per night from €95
What makes a hotel 5 stars in St. Michaels?
Impeccable guest service is the defining feature of every 5-star hotel in St. Michaels. From the moment you arrive, staff attend to your every need, whether offering luggage assistance and storage or providing a nightly turn-down service. Also, hotels must offer upscale amenities to be eligible for a 5-star rating. These can include luxury toiletries, spas or saunas, swimming pools, gastronomic restaurants and knowledgeable concierge.

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