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
10 Oct - 11 Oct
Tomorrow
11 Oct - 12 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

Our top choices for St. Michaels 5-star hotels

A room with a view of a wooden deck and a gazebo by the water.
A hotel room with a large bed, a chair, a desk, and a television.
A golf course with a water hazard and surrounding trees.
A living room with a fireplace, a sofa, a coffee table, and a television mounted on the wall.

1. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
United States
Virgilio
€504
includes taxes & fees
8 Nov - 9 Nov
Inn at Perry Cabin
A hot tub in a grassy area with a building in the background.
A cozy room with a brick fireplace, leather armchairs, and a rustic wooden table.
A room with a tufted armchair, a vase with white flowers, and a window with a view of the outdoors.
A luxurious living room with a leather sofa, a vintage trunk, and a fireplace.

2. The Inn at Tacaro Estate

The Inn at Tacaro Estate
Tracys Landing
United States
kristine
€356
includes taxes & fees
1 Nov - 2 Nov
The Inn at Tacaro Estate
Restaurant
Exterior
Staircase
Room

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
€108
12 Oct - 13 Oct
includes taxes & fees
DoubleTree by Hilton Hotel Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

126 West St Annapolis MD
€149
26 Oct - 27 Oct
includes taxes & fees
Graduate by Hilton Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4165 Mears Ave Chesapeake Beach MD
€143
26 Oct - 27 Oct
includes taxes & fees
Rod 'N' Reel Resort
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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 on stilts with a green roof, surrounded by water and greenery.
Photo by Louise Johnson

Top St. Michaels Hotel Reviews

Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"Outstanding experience in every way. Staff was superior — everyone greeted us by name and was eager to ensure we had everything we needed. Meals at Stars were excellent — and the gorgeous views of the water and property enhanced the dining experience. The lit firepits and comfy seating outside were a welcome retreat in the early evening so we could sit and take in the views. We strolled the grounds via the walking paths and enjoyed the lush gardens and plantings. All in all, an amazing getaway."
Christina 2-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 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 €108
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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