Find 5 Star Hotels in St. Michaels, MD

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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.

The Chesapeake Bay Maritime Museum in Saint Michaels, Maryland, features  the Hooper Strait Lighthouse, built in 1879

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Frequently asked questions

What are the best 5-star hotels in St. Michaels?
Treat yourself to a luxurious stay at Inn at Perry Cabin. This is among the best 5-star hotels in St. Michaels based on Expedia customer reviews. From its premium amenities and services to its prime location, you can expect the highest standard of excellence.
How much does it cost to stay in a 5-star hotel in St. Michaels?
The amount you pay for a 5-star hotel in St. Michaels depends on factors such as when you want to go and the length of your escape. A top tip for landing the best deal? Use our pricing filters to check out the available accommodations for your preferred dates.

  • Search for the lowest price per night

What makes a hotel 5 stars in St. Michaels?
In St. Michaels, a hotel needs to provide a specific amount of high-end conveniences to earn a 5-star rating. These can include saunas and spas, on-site gyms, gourmet restaurants, premium bedding, complimentary luxury toiletries and more. What also sets 5-star hotels apart is their superior service. You can expect things like in-room massages, concierge services and nightly turn-down services. Some may also offer thoughtful touches such as welcome gifts.