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

Luxury 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 Luxury Hotels

Tonight
Oct 18 - Oct 19
Tomorrow
Oct 19 - Oct 20
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Our top choices for St. Michaels luxury hotels

A room with a fireplace, a dining area with chairs, a large window with a view of the outside, and a cabinet with bottles.
A living room with a fireplace, a sofa, a coffee table, and a television mounted on the wall.
A golf course with a water hazard and surrounding trees.
A hotel room with a large bed, a chair, a desk, and a television.

1. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
  • Waterfront luxury awaits with golf, spa, and marina at this St. Michaels coastal retreat.
P30,916
P34,007 total
includes taxes & fees
Nov 18 - Nov 19
Inn at Perry Cabin
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.
A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.
A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.

2. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
P13,467
P16,550 total
includes taxes & fees
Nov 15 - Nov 16
The Inn at Chesapeake Bay Beach Club
An indoor swimming pool with lounge chairs and tables, large windows, and a high wooden ceiling.
A marina with boats docked, a sandy beach, and a clear blue sky.
A spacious dining area with high ceilings, large windows, and modern chandeliers.
A spacious dining area with a view of the water, featuring a modern design with a marble floor and contemporary furniture.

3. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
  • Chesapeake Bay resort offers luxury with private beach, full-service spa, and championship golf.
P9,195
P12,235 total
includes taxes & fees
Nov 18 - Nov 19
Hyatt Regency Chesapeake Bay
A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.
A modern salon with multiple black salon chairs, a white reception desk, and large windows allowing natural light.
A bar area with multiple screens displaying sports content, a high ceiling with geometric patterns, and a view of the outside through large windows.
A modern bar area with a long counter and multiple bar stools.

4. Rod 'N' Reel Resort

Rod 'N' Reel Resort
Chesapeake Beach
P9,106
P10,108 total
includes taxes & fees
Oct 27 - Oct 28
Rod 'N' Reel Resort
A hot tub in a grassy area with a building in the background.
A pool with two Adirondack chairs and a basket of items on the grass.
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.

5. The Inn at Tacaro Estate

The Inn at Tacaro Estate
Tracys Landing
  • Indulge in beachside luxury at this 5-star estate featuring a seasonal outdoor pool, private balconies, and Italian Frette sheets.
P22,032
P25,117 total
includes taxes & fees
Nov 1 - Nov 2
The Inn at Tacaro Estate
A wooden dock with a bench and a wooden post with a light fixture.
A corner room with a window overlooking a green field, a wooden barrel, a chair, and a small table with a candle and flowers.
A fire pit surrounded by two white chairs with blue cushions, a small table, and potted plants.
A wooden dock leading to a house with a lawn and a pond.

6. Marvel's on the Creek

Marvel's on the Creek
East New Market
P12,596
P13,982 total
includes taxes & fees
Oct 20 - Oct 21
Marvel's on the Creek
View all properties

Top St. Michaels Hotel Reviews

St Michaels Inn

St Michaels Inn

10/10 Excellent
"Great location. Very clean."
scott 2-night trip
Posted 4 hours ago
St Michaels Inn
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

8/10 Good
"Nice place, dinner staff was super slow but overall nice stay"
Richard 1-night trip
Posted 8 hours ago
Hyatt Regency Chesapeake Bay
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Extremely spacious, nicely appointed room."
r 1-night trip
Posted 9 hours ago
Graduate by Hilton Annapolis
Best Western Annapolis

Best Western Annapolis

8/10 Good
"We stay here regularly , 12 day trip this time."
scott 11-night trip
Posted 10 hours ago
Best Western Annapolis

Frequently asked questions

Are you searching for the perfect hotel for your luxury trip to St. Michaels?
During your visit, you might want to enjoy the port which St. Michaels is known for.
What's the best luxury place to stay in St. Michaels?
Inn at Perry Cabin is a luxury hotel with an ocean-view restaurant and 2 bars, and it's a popular choice for Expedia travelers looking for an elegant place to stay.
When can I expect good weather in St. Michaels?
Planning for the weather is a good way to make your trip to St. Michaels relaxing and enjoyable, especially when you're splurging. The hottest months are usually July and August with an average temp of 75°F, while the coldest months are January and February with an average of 41°F. Average annual precipitation for St. Michaels is 53 inches.
What's there to see and do in St. Michaels?
Enjoy all that St. Michaels has to offer and visit Saint Michaels Town Hall, St. Michaels Marina, and Chesapeake Bay Maritime Museum. If you have a little extra time during your trip, you might want to make a stop at St. Michaels Winery and Saint Michaels Village.

Explore a world of travel with Expedia