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

Search Luxury Hotels in St. Michaels

  • 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
11 Sept - 12 Sept
Tomorrow
12 Sept - 13 Sept
This weekend
11 Sept - 13 Sept
Next weekend
18 Sept - 20 Sept

Our top choices for St. Michaels luxury hotels

A room with a view of a wooden deck and a gazebo by the water.
A living room with a fireplace, a sofa, a coffee table, and a television mounted on the wall.
A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.
A golf course with a water hazard and surrounding trees.

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.
Rp11.370.456
Rp12.507.502 total
includes taxes & fees
6 Oct - 7 Oct
Inn at Perry Cabin
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 banquet hall with round tables set for dining, large windows with a view of a lake, and white chairs.

2. The Oaks Waterfront

The Oaks Waterfront
Easton
Rp7.722.435
Rp8.494.678 total
includes taxes & fees
13 Sept - 14 Sept
The Oaks Waterfront
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 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.

3. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
Rp3.355.864
Rp4.171.448 total
includes taxes & fees
28 Sept - 29 Sept
The Inn at Chesapeake Bay Beach Club
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 restaurant with a high ceiling, large windows, and a central bar area.

4. Rod 'N' Reel Resort

Rod 'N' Reel Resort
Chesapeake Beach
Rp2.537.033
Rp3.400.421 total
includes taxes & fees
1 Oct - 2 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 large building with a tower in the background, and a dock extending into the water.
A spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.
A marina with boats docked, a sandy beach, and a clear blue sky.

5. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
  • Chesapeake Bay resort offers luxury with private beach, full-service spa, and championship golf.
Rp3.737.511
Rp5.079.066 total
includes taxes & fees
6 Oct - 7 Oct
Hyatt Regency Chesapeake Bay
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 sunlit room with a checkered sofa, wicker chairs, a glass table, and large windows offering a view of greenery.
A fire pit surrounded by two white chairs with blue cushions, a small table, and potted plants.

6. Marvel's on the Creek

Marvel's on the Creek
East New Market
Rp3.509.400
Rp3.895.434 total
includes taxes & fees
12 Sept - 13 Sept
Marvel's on the Creek
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.

7. The Westin Annapolis

The Westin Annapolis
Annapolis
  • Historic district hotel blends Beaux Arts elegance with spa luxury, featuring lavish treatments near Annapolis attractions.
Rp3.140.913
Rp3.580.640 total
includes taxes & fees
13 Sept - 14 Sept
The Westin Annapolis
A marina with numerous boats docked, a prominent building with a dome in the background, and a clear view of the water.
A hotel lobby with a high ceiling, large windows, and a blue and white color scheme. Tables and chairs are arranged for dining or meetings.
A spacious atrium with a high ceiling, skylights, and a patterned floor.
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.

8. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
Annapolis
  • Upscale Annapolis retreat offers nautical elegance with Egyptian cotton linens and pillowtop beds.
Rp2.719.434
Rp3.100.155 total
includes taxes & fees
1 Oct - 2 Oct
Graduate by Hilton Annapolis
A balcony with a table set for two, overlooking a marina with boats.
The exterior of the Annapolis Waterfront Hotel with a clear entrance, large windows, and a bench outside.
A waterfront area with boats docked, a clear sky, and buildings in the background.
A waterfront property with a docked boat, a tall building with balconies, and a church spire in the background.

9. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
Historic District
Rp4.056.866
Rp4.624.827 total
includes taxes & fees
4 Oct - 5 Oct
Annapolis Waterfront Hotel, Autograph Collection
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 cozy room with a brick fireplace, leather armchairs, and a rustic wooden table.
A luxurious living room with a leather sofa, a vintage trunk, and a fireplace.

10. 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.
Rp6.945.388
Rp7.917.774 total
includes taxes & fees
20 Sept - 21 Sept
The Inn at Tacaro Estate
View all properties

Top St. Michaels Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

8/10 Good
"The room was clean and comfortable, however when i went to check out the élévator on my floor was n"
Jena 2-night trip
Posted 1 hour ago
DoubleTree by Hilton Hotel Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"All good."
Rod 1-night trip
Posted 3 hours ago
Crowne Plaza Annapolis by IHG
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Great property and a great low key spot for a couple."
Will 1-night trip
Posted 6 hours ago
St Michaels Inn
Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"It’s so lovely and elegant I almost don’t want to tell people it’s there. Stunning, perfect in every way."
Susan 1-night trip
Posted 3 days ago
Inn at Perry Cabin

Frequently asked questions

Are you searching for the perfect hotel for your luxury holiday in St. Michaels?
During your visit, you might want to enjoy the port which St. Michaels is known for.
What's the best luxury accommodation option 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 travellers 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 temperature of 24°C, while the coldest months are January and February, with an average of 5°C. Average annual precipitation for St. Michaels is 1341 mm.
What's there to see and do in St. Michaels?
Enjoy all that St. Michaels has to offer and visit St. Michaels Marina, Chesapeake Bay Maritime Museum and St. Michaels Winery. If you have a little extra time during your trip, you might want to make a stop at Saint Michaels Village and Higgins Yacht Yard and Marina.

Explore a world of travel with Expedia