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

Luxury Hotels in St. Michaels, Maryland

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Check availability on St. Michaels Luxury Hotels

Our top choices for St. Michaels luxury hotels

Breakfast, lunch, dinner and brunch served

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (393 reviews)
  • cleanliness
    Waterfront luxury awaits with golf, spa, and marina at this St. Michaels coastal retreat.
The price is P39,975
P43,973 total
includes taxes & fees
Aug 19 - Aug 20
Inn at Perry Cabin
Private kitchen

The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (42 reviews)
The price is P27,107
P29,818 total
includes taxes & fees
Jul 28 - Jul 29
The Oaks Waterfront
Front of property - evening/night

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (468 reviews)
The price is P14,532
P17,700 total
includes taxes & fees
Aug 2 - Aug 3
The Inn at Chesapeake Bay Beach Club
Dock

Marvel's on the Creek

Marvel's on the Creek
4.0 star property
East New Market
10.0 out of 10, Exceptional, (168 reviews)
The price is P12,319
P13,674 total
includes taxes & fees
Jul 22 - Jul 23
Marvel's on the Creek
Outdoor wedding area

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,006 reviews)
The price is P11,733
P15,074 total
includes taxes & fees
Aug 12 - Aug 13
Rod 'N' Reel Resort
Lobby

The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,003 reviews)
  • cleanliness
    Historic district hotel blends Beaux Arts elegance with spa luxury, featuring lavish treatments near Annapolis attractions.
The price is P12,257
P13,973 total
includes taxes & fees
Jul 26 - Jul 27
The Westin Annapolis
Indoor pool, 2 outdoor pools, pool umbrellas, sun loungers

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
4.0 star property
Cambridge
8.8 out of 10, Excellent, (1,002 reviews)
  • cleanliness
    Chesapeake Bay resort offers luxury with private beach, full-service spa, and championship golf.
The price is P17,890
P23,248 total
includes taxes & fees
Jul 28 - Jul 29
Hyatt Regency Chesapeake Bay
Premium bedding, down comforters, pillowtop beds, in-room safe

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (947 reviews)
The price is P13,617
P15,524 total
includes taxes & fees
Aug 18 - Aug 19
Annapolis Waterfront Hotel, Autograph Collection
View from property

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1,005 reviews)
  • cleanliness
    Upscale Annapolis retreat offers nautical elegance with Egyptian cotton linens and pillowtop beds.
The price is P10,313
P11,757 total
includes taxes & fees
Jul 26 - Jul 27
Graduate by Hilton Annapolis
Reception

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,043 reviews)
The price is P7,031
P8,016 total
includes taxes & fees
Aug 20 - Aug 21
DoubleTree by Hilton Hotel Annapolis
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Top St. Michaels Hotel Reviews

Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"Beautiful property, very well maintained. Dinner and Brunch at Stars were both very good. We loved being by the boats. Staff was accommodating when I had to do a zoom call on the morning of departure and found me a quiet private spot. Short walk to the Maritime Museum which was worth going to learn about the Eastern Shore. Short walk to town to pick up some needed items at the local pharmacy and on the way back stopped at the olive oil store and bought a couple of interesting bottles. Would have like to check out the SPA, but we decided on Friday to spend Saturday and Sunday nights and they were booked. The staff was generally friendly. It was expensive per night. But for clean and beautiful grounds, a clean room, friendly staff, and views from our room and from the restaurants that included water and boats, I felt it was worth it for our spontaneous road trip from the Philly suburb. We would come back and this time book a sailing activity and a massage. Notes: The big Samsung TV was nice but doesn't allow streaming from my phones and so we had to watch our show on my laptop. Room #2 was great in that it was in the main lodge next to the restaurant and a across from the bar which was very noisy at times. We didn't mind for 2 days, we enjoyed the convenience and drowned at noisy with a sound machine. If we were there for longer, the noise may have gotten old. In summary, we liked it and would visit again."
Greg 2-night trip
Posted less than an hour 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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