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

St. Michaels 5 Stars Hotels

  • 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

Tonight
Sep 19 - Sep 20
Tomorrow
Sep 20 - Sep 21
Next weekend
Sep 25 - Sep 27
In two weeks
Oct 2 - Oct 4

Our top choices for St. Michaels 5-star hotels

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

1. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
United States
Andrew
NT$19,190
NT$21,109 total
includes taxes & fees
Oct 13 - Oct 14
Inn at Perry Cabin
Seasonal outdoor pool, pool umbrellas, sun loungers
Frette Italian sheets, premium bedding, down comforters, WiFi (free)
Taylor's Suite | Frette Italian sheets, premium bedding, down comforters, WiFi (free)
Interior

2. The Inn at Tacaro Estate

The Inn at Tacaro Estate
Tracys Landing
United States
James
NT$12,622
NT$14,390 total
includes taxes & fees
Oct 13 - Oct 14
The Inn at Tacaro Estate
Dinner served
Interior
The Asian Suite | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds
Staircase

3. Inn at 202 Dover

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

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD
NT$2,640
NT$3,009 total
Sep 27 - Sep 28
includes taxes & fees
8.8/10 Excellent! (1,187 reviews)
DoubleTree by Hilton Hotel Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

126 West St Annapolis MD
NT$4,743
NT$5,407 total
Sep 27 - Sep 28
includes taxes & fees
Graduate by Hilton Annapolis
The Westin Annapolis

The Westin Annapolis

100 Westgate Cir Annapolis MD
NT$5,697
NT$6,494 total
Sep 27 - Sep 28
includes taxes & fees
The Westin Annapolis
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.
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 with a balcony, a bell, and a grassy area with a path leading to it.
Photo by JensTrvlBug

Top St. Michaels Hotel Reviews

Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"It’s so lovely and elegant I almost don’t want to tell people it’s there. Stunning, perfect in every way."
Susan 1-night trip
Posted 11 days ago
Inn at Perry Cabin

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 accommodations 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 NT$3,009
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.

Explore a world of travel with Expedia