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

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 golf course with a water hazard and surrounding trees.
A swimming pool with white lounge chairs and blue umbrellas, surrounded by 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.
฿17,260
฿18,986 total
includes taxes & fees
8 Nov - 9 Nov
Inn at Perry Cabin
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
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.
A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.

2. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
฿6,429
฿7,992 total
includes taxes & fees
19 Oct - 20 Oct
The Inn at Chesapeake Bay Beach Club
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 marina with boats docked, a sandy beach, and a clear blue sky.
A spacious dining area with high ceilings, large windows, and modern chandeliers.

3. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
  • Chesapeake Bay resort offers luxury with private beach, full-service spa, and championship golf.
฿5,989
฿7,758 total
includes taxes & fees
4 Nov - 5 Nov
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 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
฿4,861
฿5,395 total
includes taxes & fees
2 Nov - 3 Nov
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 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.

5. Marvel's on the Creek

Marvel's on the Creek
East New Market
฿6,723
฿7,463 total
includes taxes & fees
9 Oct - 10 Oct
Marvel's on the Creek
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 room with a tufted armchair, a vase with white flowers, and a window with a view of the outdoors.
A cozy room with a brick fireplace, leather armchairs, and a rustic wooden table.

6. 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.
฿11,770
฿13,418 total
includes taxes & fees
1 Nov - 2 Nov
The Inn at Tacaro Estate
View all properties

Top St. Michaels Hotel Reviews

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 2 hours ago
DoubleTree by Hilton Hotel Annapolis
Best Western Annapolis

Best Western Annapolis

10/10 Excellent
"For hotel employees — do hotels actually keep internal notes/ratings about guests? Like behavior, complaints, being rude, special requests, etc.? Just curious how much gets tracked behind the scenes. Upvote 195 Downvote 170 Go to comments"
Juan C 1-night trip
Posted 6 hours ago
Best Western Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Great location"
Jose 1-night trip
Posted 9 hours ago
Crowne Plaza Annapolis by IHG
Historic Inns of Annapolis

Historic Inns of Annapolis

8/10 Good
"Only complaint was no coffee or cups. And lightbulbs were out."
Perry 1-night trip
Posted 1 day ago
Historic Inns of Annapolis
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"Staff was great, hotel needs real renovation seems like they've done a lot of patch work. Parking should be complimentary for people staying in the hotel or a discounted rate. $35 a day for parking at the hotel you're staying at is crazy. There's very limited parking to begin with."
Lauren 2-night trip
Posted 2 days ago
Hilton Garden Inn Annapolis Downtown
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Late night manager was extremely helpful!"
Rodney 1-night trip
Posted 6 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 8 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 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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