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
Sep 26 - Sep 27
Tomorrow
Sep 27 - Sep 28
Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11

Our top choices for St. Michaels luxury hotels

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

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.
￥80,685
￥88,754 total
includes taxes & fees
Oct 26 - Oct 27
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 white colonial-style house with a covered porch, brick steps, and outdoor seating.
A deck with wicker furniture, a table, and an umbrella, overlooking a lake with trees and a dock.

2. The Oaks Waterfront

The Oaks Waterfront
Easton
￥69,219
￥76,141 total
includes taxes & fees
Sep 27 - Sep 28
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
￥30,080
￥37,390 total
includes taxes & fees
Oct 19 - Oct 20
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 salon with multiple black salon chairs, a white reception desk, and large windows allowing natural light.
A modern bar area with a long counter and multiple bar stools.
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
￥21,376
￥28,964 total
includes taxes & fees
Oct 11 - Oct 12
Rod 'N' Reel Resort
An indoor swimming pool with lounge chairs and tables, large windows, and a high wooden ceiling.
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.
A spacious dining area with high ceilings, large windows, and modern chandeliers.

5. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
  • Chesapeake Bay resort offers luxury with private beach, full-service spa, and championship golf.
￥33,186
￥45,169 total
includes taxes & fees
Oct 26 - Oct 27
Hyatt Regency Chesapeake Bay
A wooden dock with a bench and a wooden post with a light fixture.
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 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.

6. Marvel's on the Creek

Marvel's on the Creek
East New Market
￥28,625
￥31,775 total
includes taxes & fees
Oct 18 - Oct 19
Marvel's on the Creek
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.

7. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
Annapolis
  • Upscale Annapolis retreat offers nautical elegance with Egyptian cotton linens and pillowtop beds.
￥23,086
￥26,318 total
includes taxes & fees
Oct 26 - Oct 27
Graduate by Hilton Annapolis
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 modern living room with a sofa, armchairs, a coffee table, and a fireplace.
A restaurant with wooden tables and chairs, a bar area, and a tiled floor.

8. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
￥15,238
￥17,371 total
includes taxes & fees
Sep 29 - Sep 30
DoubleTree by Hilton Hotel Annapolis
A hot tub in a grassy area with a building in the background.
A room with a tufted armchair, a vase with white flowers, and a window with a view of the outdoors.
A pool with two Adirondack chairs and a basket of items on the grass.
A luxurious living room with a leather sofa, a vintage trunk, and a fireplace.

9. 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.
￥62,382
￥71,115 total
includes taxes & fees
Sep 27 - Sep 28
The Inn at Tacaro Estate
A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.
A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.
A store with shelves of beverages, a counter with a cash register, and baskets with items.
A modern hotel lobby with a curved seating area, a bar, and a large bookshelf.

10. The Westin Annapolis

The Westin Annapolis
Annapolis
  • Historic district hotel blends Beaux Arts elegance with spa luxury, featuring lavish treatments near Annapolis attractions.
￥31,299
￥35,681 total
includes taxes & fees
Oct 25 - Oct 26
The Westin Annapolis
View all properties

Top St. Michaels Hotel Reviews

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"Loved everything about it but especially the staff was so friendly and accommodating!"
petra 6-night trip
Posted 6 hours ago
Hilton Garden Inn Annapolis Downtown
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

10/10 Excellent
"My room was nice, clean and cozy"
jerria 2-night trip
Posted 15 hours ago
Hyatt Regency Chesapeake Bay
Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"The room was perfect. The location was amazing!"
Nicole 1-night trip
Posted 22 hours ago
Historic Inns of Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"I liked the staff!"
Elliott 1-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Annapolis

Frequently asked questions

Are you searching for the perfect hotel for your luxury trip to St. Michaels?
During your visit, you might want to enjoy the port which St. Michaels is known for.
What's the best luxury place to stay 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 travelers 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 temp of 75°F, while the coldest months are January and February with an average of 41°F. Average annual precipitation for St. Michaels is 53 inches.
What's there to see and do in St. Michaels?
Enjoy all that St. Michaels has to offer and visit Saint Michaels Town Hall, St. Michaels Marina, and Chesapeake Bay Maritime Museum. If you have a little extra time during your trip, you might want to make a stop at St. Michaels Winery and Saint Michaels Village.

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