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
Oct 8 - Oct 9
Tomorrow
Oct 9 - Oct 10
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for St. Michaels luxury hotels

A room with a view of a wooden deck and a gazebo by the water.
A hotel room with a large bed, a chair, a desk, and a television.
A living room with a fireplace, a sofa, a coffee table, and a television mounted on the wall.
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.
￥81,054
￥89,159 total
includes taxes & fees
Nov 8 - Nov 9
Inn at Perry Cabin
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
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.
A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

2. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
￥30,252
￥37,604 total
includes taxes & fees
Nov 2 - Nov 3
The Inn at Chesapeake Bay Beach Club
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 marina with boats docked, a large building with a tower in the background, and a dock extending into the water.

3. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
  • Chesapeake Bay resort offers luxury with private beach, full-service spa, and championship golf.
￥28,156
￥36,475 total
includes taxes & fees
Nov 4 - Nov 5
Hyatt Regency Chesapeake Bay
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 bar area with multiple screens displaying sports content, a high ceiling with geometric patterns, and a view of the outside through large windows.
A modern bar area with a long counter and multiple bar stools.

4. Rod 'N' Reel Resort

Rod 'N' Reel Resort
Chesapeake Beach
￥20,789
￥23,076 total
includes taxes & fees
Nov 1 - Nov 2
Rod 'N' Reel Resort
A hot tub in a grassy area with a building in the background.
A cozy room with a brick fireplace, leather armchairs, and a rustic wooden table.
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.

5. 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.
￥48,641
￥55,450 total
includes taxes & fees
Nov 2 - Nov 3
The Inn at Tacaro Estate
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 sunlit room with a checkered sofa, wicker chairs, a glass table, and large windows offering a view of greenery.
A corner room with a window overlooking a green field, a wooden barrel, a chair, and a small table with a candle and flowers.

6. Marvel's on the Creek

Marvel's on the Creek
East New Market
￥28,440
￥31,569 total
includes taxes & fees
Oct 9 - Oct 10
Marvel's on the Creek
View all properties

Top St. Michaels Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Nice"
James 1-night trip
Posted 2 hours ago
Historic Inns of Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Everything was great. Staff was very helpful"
Chanta 1-night trip
Posted 19 hours ago
DoubleTree by Hilton Hotel Annapolis
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Late night manager was extremely helpful!"
Rodney 1-night trip
Posted 7 days ago
St Michaels Inn
Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"Outstanding experience in every way. Staff was superior — everyone greeted us by name and was eager to ensure we had everything we needed. Meals at Stars were excellent — and the gorgeous views of the water and property enhanced the dining experience. The lit firepits and comfy seating outside were a welcome retreat in the early evening so we could sit and take in the views. We strolled the grounds via the walking paths and enjoyed the lush gardens and plantings. All in all, an amazing getaway."
Christina 2-night trip
Posted 9 days ago
Inn at Perry Cabin

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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