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

St. Michaels Hotel Guide - 4 Stars Hotels in St. Michaels, Maryland

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Check availability on St. Michaels 4 Star Hotels

Tonight
21 Sept - 22 Sept
Tomorrow
22 Sept - 23 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

Our top choices for St. Michaels 4-star hotels

A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.
A DoubleTree by Hilton hotel entrance with a brick facade, a gated driveway, and a clear sky.
A spacious lobby with a high ceiling, a central seating area with sofas and tables, and large windows with curtains.
A modern living room with a sofa, armchairs, a coffee table, and a fireplace.

1. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
United States
Michele
Rp1.472.902
Rp1.679.108 total
includes taxes & fees
27 Sept - 28 Sept
DoubleTree by Hilton Hotel Annapolis
A marina with numerous boats docked, a prominent building with a dome in the background, and a clear view of the water.
A bar with a brick wall, a mounted shark, and various bottles and glasses on shelves.
A modern lounge area with a blue sofa, red chairs, and plaid armchairs. A coffee table with books and a vase of flowers is in the center. Large windows offer a view of a brick building with awnings.
A spacious atrium with a high ceiling, skylights, and a patterned floor.

2. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
Annapolis
United States
Boryana
Rp2.640.970
Rp3.010.706 total
includes taxes & fees
27 Sept - 28 Sept
Graduate by Hilton Annapolis
A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.
A modern hotel lobby with a curved seating area, a bar, and a large bookshelf.
A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.

3. The Westin Annapolis

The Westin Annapolis
Annapolis
United States
Bobbi
Rp3.178.682
Rp3.623.698 total
includes taxes & fees
27 Sept - 28 Sept
The Westin Annapolis
A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.
A modern bar area with a long counter and multiple bar stools.
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.

4. Rod 'N' Reel Resort

Rod 'N' Reel Resort
Chesapeake Beach
United States
Francine
Rp2.567.541
Rp3.441.311 total
includes taxes & fees
7 Oct - 8 Oct
Rod 'N' Reel Resort
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 multiple tables and chairs, high ceilings with exposed beams, and a brick wall.
A spacious dining area with high ceilings, large windows, and modern chandeliers.

5. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
United States
Jon
Rp3.871.244
Rp5.240.918 total
includes taxes & fees
13 Oct - 14 Oct
Hyatt Regency Chesapeake Bay
A balcony with a table set for two, overlooking a marina with boats.
A waterfront area with boats docked, a clear sky, and buildings in the background.
The exterior of the Annapolis Waterfront Hotel with a clear entrance, large windows, and a bench outside.
A hotel room with a large bed, a chair, a small table, and a view of a body of water.

6. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
Historic District
United States
William
Rp4.105.650
Rp4.680.441 total
includes taxes & fees
4 Oct - 5 Oct
Annapolis Waterfront Hotel, Autograph Collection
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.
A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.

7. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
United States
scott
Rp3.396.217
Rp4.221.565 total
includes taxes & fees
19 Oct - 20 Oct
The Inn at Chesapeake Bay Beach Club
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.
A wooden console table with framed floral artwork, two lamps, and two ottomans.
A deck with wicker furniture, a table, and an umbrella, overlooking a lake with trees and a dock.
A white colonial-style house with a covered porch, brick steps, and outdoor seating.

8. The Oaks Waterfront

The Oaks Waterfront
Easton
United States
Jeffrey
Rp7.815.296
Rp8.596.825 total
includes taxes & fees
24 Sept - 25 Sept
The Oaks Waterfront
A wooden dock with a bench and a wooden post with a light fixture.
A wooden dock leading to a house with a lawn and a pond.
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 sunlit room with a checkered sofa, wicker chairs, a glass table, and large windows offering a view of greenery.

9. Marvel's on the Creek

Marvel's on the Creek
East New Market
United States
Richard
Rp3.551.600
Rp3.942.276 total
includes taxes & fees
22 Sept - 23 Sept
Marvel's on the Creek
A multi-story residential building with a covered porch and a red umbrella.
A marina with boats docked, a large building with a white facade, and a clear blue sky.
A modern kitchen with grey cabinets, a central island, and a dining area with a table and chairs.
A modern kitchen with grey cabinets, stainless steel appliances, and a central island.

10. Walk to Dtwn: Waterfront Eastern Shore Townhome!

Walk to Dtwn: Waterfront Eastern Shore Townhome!
Cambridge
Walk to Dtwn: Waterfront Eastern Shore Townhome!
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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
Rp10.708.074
Rp11.778.881 total
13 Oct - 14 Oct
includes taxes & fees
9.6/10 Exceptional! (403 reviews)
Inn at Perry Cabin
The Inn at Tacaro Estate

The Inn at Tacaro Estate

6220 Town Point Rd Tracys Landing MD
Rp7.043.356
Rp8.029.457 total
4 Oct - 5 Oct
includes taxes & fees
9.6/10 Exceptional! (19 reviews)
The Inn at Tacaro Estate
Inn at 202 Dover

Inn at 202 Dover

202 East Dover Street Easton MD
Get ratesInn at 202 Dover
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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

The Westin Annapolis

The Westin Annapolis

8/10 Good
"Room was clean upon arrival but they didn’t clean it the following day. We had to ask front desk twice to send up someone to clean it and this didn’t happen till 4:00 !!!! We were out of the room All day and they could have cleaned it anytime ! Don’t drink at hotel bar !!! Expensive. Restaurant across street at Carpaccio restaurant bar. Drink was $5 cheaper AND $9 cheaper at happy hour. Breakfast was great in hotel and staff was more than nice."
JOYCE ANN 2-night trip
Posted 8 hours ago
The Westin Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Excellent location, clean and comfortable room. It's our second time staying here and looking forward to returning."
Julie 2-night trip
Posted 1 day ago
DoubleTree by Hilton Hotel Annapolis
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"This is a great hotel in a great location two great restaurants."
William 1-night trip
Posted 7 days ago
Annapolis Waterfront Hotel, Autograph Collection

Frequently asked questions

How much does it cost to stay in a 4-star hotel in St. Michaels?
With Expedia's search and sort filters, scoring a superb deal on a 4-star hotel in St. Michaels just got easier. Start by keying in your chosen travel dates and length of your escape. Then sort the results by price and choose a property that best suits your budget and style.
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What's the difference between 5-star and 4-star hotels in St. Michaels?
Offering an inviting traveller experience and upmarket surroundings, 4-star hotels are a fantastic option for your St. Michaels break. These types of stays generally feature loads of useful amenities that make it easy to kick back and relax — think 24-hour room service, restaurants and pools. Or live the high life at a 5-star hotel designed to pamper with luxury perks and amenities. A personalised service, premium toiletries and world-class dining are typically included at these plush retreats.
Does St. Michaels have any 4-star all-inclusive resorts?
Use our "All inclusive" filter to search for your next escape in St. Michaels where everything is taken care of, from your accommodation to your food, activities and entertainment. We can also help you find standard 4-star stays in and around this much-loved destination.

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