Compare and book 4 Star hotels in St. Michaels, Maryland

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Check availability on St. Michaels 4 Star Hotels

Tonight
6 Dec - 7 Dec
Tomorrow
7 Dec - 8 Dec
Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec

Top St. Michaels 4 Star Hotels

Garden
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4.0 star property
Annapolis
8.6 out of 10, Excellent, (1006)
"Great place!"
United States
Tawnya
The price is 2.183.384 ₫
2.489.058 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
DoubleTree by Hilton Hotel Annapolis
View from property
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1001)
"Very nice hotel. The dog park could have better lighting. "
United States
Andrew
The price is 3.338.874 ₫
3.806.315 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Graduate by Hilton Annapolis
Indoor pool, 2 outdoor pools, pool umbrellas, pool loungers
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4.0 star property
Cambridge
8.8 out of 10, Excellent, (1000)
"Very courteous staff."
United States
Joseph
The price is 4.683.387 ₫
6.027.445 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Hyatt Regency Chesapeake Bay
Room, 2 Queen Beds, Balcony | Premium bedding, down duvets, pillow-top beds, in-room safe
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
Historic District
8.8 out of 10, Excellent, (879)
"Great location, nice and clean "
United States
Micah
The price is 4.683.387 ₫
5.339.062 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Annapolis Waterfront Hotel, Autograph Collection
View from property
The Westin Annapolis

The Westin Annapolis

4.0 star property
Annapolis
8.6 out of 10, Excellent, (1000)
"Great environment"
United States
Salvador E
The price is 4.059.902 ₫
4.628.289 ₫ total
includes taxes & fees
14 Dec - 15 Dec
The Westin Annapolis
Balcony
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4.0 star property
Chesapeake Beach
8.4 out of 10, Very good, (1000)
"The hotel is beautiful I can’t wait for"
United States
Lynn
The price is 2.803.309 ₫
3.638.934 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
Rod 'N' Reel Resort
Front of property – evening/night
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, (429)
"Very nice atmosphere. Fall decor, multiple outdoor fireplaces, water fountains, everything clean, tidy, cozy, and all staff professionally courteous. Just very pleasant all around."
United States
Warren
The price is 4.846.722 ₫
6.050.537 ₫ total
includes taxes & fees
9 Dec - 10 Dec
The Inn at Chesapeake Bay Beach Club
Front of property
The Oaks Waterfront

The Oaks Waterfront

4.0 star property
Easton
10.0 out of 10, Exceptional, (41)
"Loved the Oaks! Fabulous accommodations and excellent staff"
United States
Barbara
The price is 10.890.555 ₫
11.979.611 ₫ total
includes taxes & fees
7 Dec - 8 Dec
The Oaks Waterfront
Dock
Marvel's on the Creek

Marvel's on the Creek

4.0 star property
East New Market
10.0 out of 10, Exceptional, (161)
"Clean & spacious room. Amazing hospitality. Excellent communication!"
United States
Chin
The price is 5.272.600 ₫
5.852.586 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Marvel's on the Creek
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Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in St. Michaels.
Inn at Perry Cabin

Inn at Perry Cabin

308 Watkins Ln St. Michaels MD
The price is 12.693.784 ₫ per night from 7 Dec to 8 Dec
12.693.784 ₫
15.359.611 ₫ total
7 Dec - 8 Dec
includes taxes & fees
9.4/10 Exceptional! (370 reviews)
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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
The Chesapeake Bay Maritime Museum in Saint Michaels, Maryland, features the Hooper Strait Lighthouse, built in 1879

Top St. Michaels Hotel Reviews

Frequently asked questions

How much does it cost to stay in a 4-star hotel in St. Michaels?
With Expedia's handy search filters, scoring a great deal on a 4-star hotel in St. Michaels just got easier. Start by keying in your chosen arrival date and length of your escape. Then list the results by price and pick a property that best suits your style and budget.

  • Search for the lowest price from 15.359.611 ₫

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.

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