Aerial panorama of shipyard and lighthouse in St. Michaels harbor in Maryland in the Chesapeake Bay

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Our top choices for St. Michaels 4-star hotels

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (936 reviews)
"Definitely the view of the harbor from our room and how all the stores and restaurants were in walking distance"
United States
Salvatore
The price is £231
includes taxes & fees
7 Jul - 8 Jul
Annapolis Waterfront Hotel, Autograph Collection

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,015 reviews)
"It was one of the nicest places we've stayed in our travels."
United States
William
The price is £95
includes taxes & fees
15 Jun - 16 Jun
DoubleTree by Hilton Hotel Annapolis

The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,001 reviews)
"Good location, nice hotel"
United States
Jiyoung
The price is £161
includes taxes & fees
2 Jul - 3 Jul
The Westin Annapolis

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
4.0 star property
Cambridge
8.8 out of 10, Excellent, (1,007 reviews)
"The hotel was very nice enjoyed my stay."
United States
Raquel
The price is £295
includes taxes & fees
6 Jul - 7 Jul
Hyatt Regency Chesapeake Bay

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1,006 reviews)
"Very fine place"
United States
David
The price is £153
includes taxes & fees
5 Jul - 6 Jul
Graduate by Hilton Annapolis

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,001 reviews)
"Awesome spot and room, nice walking distance from multiple places"
United States
Travis
The price is £142
includes taxes & fees
22 Jun - 23 Jun
Rod 'N' Reel Resort

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (457 reviews)
"The entire place was beautiful, the staff, room, shops, restaurants all were amazing. Thanks"
United States
Winfred
The price is £206
includes taxes & fees
15 Jun - 16 Jun
The Inn at Chesapeake Bay Beach Club

The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (41 reviews)
"Staff, breakfast, and room were all superb!"
United States
Jeffrey
The price is £362
includes taxes & fees
14 Jun - 15 Jun
The Oaks Waterfront

Marvel's on the Creek

Marvel's on the Creek
4.0 star property
East New Market
10.0 out of 10, Exceptional, (166 reviews)
"Always a great time staying here."
United States
Richard
The price is £150
includes taxes & fees
15 Jun - 16 Jun
Marvel's on the Creek

Walk to Dtwn: Waterfront Eastern Shore Townhome!

Walk to Dtwn: Waterfront Eastern Shore Townhome!
4.0 star property
Cambridge
Walk to Dtwn: Waterfront Eastern Shore Townhome!
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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

Top St. Michaels Hotel Reviews

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Frequently asked questions

How much does it cost to stay in a 4-star hotel in St. Michaels?
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What's the difference between 5-star and 4-star hotels in St. Michaels?
Offering a friendly traveller experience and upmarket surroundings, 4-star hotels are an excellent option for your St. Michaels break. These types of stays generally come with lots of useful amenities that make it easy to unpack and relax — think pillowtop mattresses, gyms and pools. Or get a taste of the high life at a 5-star hotel designed to indulge you in luxury perks and amenities. Round-the-clock concierge service, complimentary toiletries and gourmet dining are typically included at these swanky retreats.
Does St. Michaels have any 4-star all-inclusive resorts?
Enjoy a relaxing holiday experience where everything is included in the one upfront rate by using our "All inclusive" filter. Budgeting is a piece of cake when your room, food, activities and entertainment are already taken care of. Eager for more options? Browse the incredible deals on Expedia's standard 4-star options in and around St. Michaels too.