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

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Check availability on St. Michaels Luxury Hotels

Tonight
21 Aug - 22 Aug
Tomorrow
22 Aug - 23 Aug
This weekend
21 Aug - 23 Aug
Next weekend
28 Aug - 30 Aug

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 hotel room with a large bed, a chair, a desk, and a television.
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.
S$595
includes taxes & fees
7 Sept - 8 Sept
Inn at Perry Cabin
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.
A banquet hall with round tables set for dining, large windows with a view of a lake, and white chairs.
A white colonial-style house with a covered porch, brick steps, and outdoor seating.
A wooden console table with framed floral artwork, two lamps, and two ottomans.

2. The Oaks Waterfront

The Oaks Waterfront
Easton
S$615
includes taxes & fees
3 Sept - 4 Sept
The Oaks Waterfront
A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.
A staircase with a wooden handrail, a blue wall, and a ceiling light fixture.
A modern bar area with a long counter and multiple bar stools.
A restaurant with a high ceiling, large windows, and a central bar area.

3. Rod 'N' Reel Resort

Rod 'N' Reel Resort
Chesapeake Beach
S$191
includes taxes & fees
3 Sept - 4 Sept
Rod 'N' Reel Resort
A wooden dock with a bench and a wooden post with a light fixture.
A fire pit surrounded by two white chairs with blue cushions, a small table, and potted plants.
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.

4. Marvel's on the Creek

Marvel's on the Creek
East New Market
S$262
includes taxes & fees
30 Aug - 31 Aug
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 store with shelves of beverages, a counter with a cash register, and baskets with items.
A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.

5. The Westin Annapolis

The Westin Annapolis
Annapolis
  • Historic district hotel blends Beaux Arts elegance with spa luxury, featuring lavish treatments near Annapolis attractions.
S$245
includes taxes & fees
30 Aug - 31 Aug
The Westin Annapolis
A balcony with a table set for two, overlooking a marina with boats.
A hotel room with a large bed, a chair, a small table, and a view of a body of water.
A waterfront property with a docked boat, a tall building with balconies, and a church spire in the background.
The exterior of the Annapolis Waterfront Hotel with a clear entrance, large windows, and a bench outside.

6. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
Historic District
S$300
includes taxes & fees
30 Aug - 31 Aug
Annapolis Waterfront Hotel, Autograph Collection
A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.
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.
A DoubleTree by Hilton hotel entrance with a brick facade, a gated driveway, and a clear sky.

7. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
S$141
includes taxes & fees
30 Aug - 31 Aug
DoubleTree by Hilton Hotel Annapolis
View all properties

Top St. Michaels Hotel Reviews

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Rooms where clean, staff was nice"
Debra 1-night trip
Posted 6 hours ago
Crowne Plaza Annapolis by IHG
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

10/10 Excellent
"Excellent well-maintained rooms with new ceiling fan. Summer amenities are geared to families and include mini golf, multiple pools indoors & outdoors, day spa, convenience shop with coffee , pool tables (although not as well maintained as other areas of the property), walking paths, and a regulationgolf course. Families can be quite boisterous; we will opt for calmer winter months in future."
Annette 2-night trip
Posted 16 hours ago
Hyatt Regency Chesapeake Bay
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

8/10 Good
"Reasonable value for the money"
Frank 1-night trip
Posted 1 day ago
Holiday Inn Express & Suites Annapolis by IHG
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Clean and comfortable room, helpful staff and great room service!"
Catherine 1-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Annapolis
Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"Amazing experience highly recommend"
Andrew 2-night trip
Posted 5 days ago
Inn at Perry Cabin
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Breakfast bacon was inedible, but breakfast otherwise substantial."
Maureen 1-night trip
Posted 6 days ago
Country Inn & Suites by Radisson, Annapolis, MD

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 Saint Michaels Town Hall.

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