Compare and book 5 Star hotels in St. Michaels, 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 St. Michaels 5 Star Hotels

Our top choices for St. Michaels 5-star hotels

Premium bedding, down duvets, in-room safe, desk

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (374 reviews)
"Fantastic resort; beautiful with lots of great history. Highly recommend the historic walking tour with Jay. "
United States
Joseph
The price is 9.712.287 ₫
10.683.516 ₫ total
includes taxes & fees
11 Mar - 12 Mar
Inn at Perry Cabin
Seasonal outdoor pool, pool umbrellas, pool loungers

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.4 out of 10, Exceptional, (12 reviews)
"Wonderful experience Felt like being in good friends home without having to help with the dishes Luxurious stay Recommend *****"
United States
Todd
The Inn at Tacaro Estate
Dinner served

Inn at 202 Dover

Inn at 202 Dover
5.0 star property
Easton
10.0 out of 10, Exceptional, (14 reviews)
"Celebrated our 33rd anniversary here and enjoyed it thoroughly. Felt pampered and welcomed. Best B&B ever! Everything from the room to the food was exceptional. Every need was anticipated and met. Looking forward to our next visit. The quintessential "living like a king" experience."
United States
James
Inn at 202 Dover
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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
The price is 2.348.638 ₫ per night from 15 Mar to 16 Mar
2.348.638 ₫
2.677.447 ₫ total
15 Mar - 16 Mar
includes taxes & fees
8.6/10 Excellent! (1,021 reviews)
Still don't see what you're looking for?
See all properties in St. Michaels.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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
The Chesapeake Bay Maritime Museum in Saint Michaels, Maryland, features the Hooper Strait Lighthouse, built in 1879

Top St. Michaels Hotel Reviews

Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"We had a great stay, hotel was very clean and food was great"
Jonathan 1-night trip
Posted 2 months ago
Inn at Perry Cabin

Frequently asked questions

What are the best 5-star hotels in St. Michaels?
Offering world-class amenities and services, our travellers rate Inn at Perry Cabin as among the best 5-star hotels in St. Michaels. You'll be in the lap of luxury from the minute you step into the lobby.
How much does it cost to stay in a 5-star hotel in St. Michaels?
There are a variety of pricing options for 5-star hotels in St. Michaels on Expedia. The amount you pay will depend on when you plan to travel, trip length and other factors. Compare all of the available properties for your preferred dates and make use of our pricing and other filters to land the ideal luxury stay.

  • Search for the lowest price per night from 2.677.447 ₫

What makes a hotel 5 stars in St. Michaels?
In St. Michaels, a hotel needs to offer a certain number of upscale features to earn 5 stars. These can include on-site gyms, spas and saunas, gourmet restaurants, premium bedding, luxury bathroom products and more. What also sets 5-star hotels apart is their outstanding standard of service. You can look forward to things like concierge services, nightly turn-down services and in-room massage. Some may even offer extra touches like a welcome gift.