Find Luxury Hotels in St. Michaels, MD

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on St. Michaels Luxury Hotels

Our top choices for St. Michaels luxury hotels

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (383 reviews)
  • cleanliness
    Waterfront luxury awaits with golf, spa, and marina at this St. Michaels coastal retreat.
"The Inn at Perry Cabin is great for a romantic getaway. The staff pampers their guests in an attentive but un-intrusive way. The food service is excellence and the entire vibe is under stated elegance. "
United States
Edmond
The price is ¥94,478
¥103,926 total
includes taxes & fees
May 28 - May 29
Inn at Perry Cabin

Marvel's on the Creek

Marvel's on the Creek
4.0 star property
East New Market
10.0 out of 10, Exceptional, (162 reviews)
"Beautiful waters views. Host was very welcoming. Breakfast was great."
United States
Adrian
The price is ¥28,202
¥31,304 total
includes taxes & fees
May 12 - May 13
Marvel's on the Creek

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.6 out of 10, Exceptional, (15 reviews)
  • cleanliness
    Indulge in beachside luxury at this 5-star estate featuring a seasonal outdoor pool, private balconies, and Italian Frette sheets.
"It was amazing. The place was nicely decorated. Food was great. Highly recommended."
United States
Anonymous traveler
The price is ¥46,548
¥53,065 total
includes taxes & fees
May 17 - May 18
The Inn at Tacaro Estate

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, (453 reviews)
"Great view of the Bay Bridge and the water."
United States
Robert
The price is ¥35,349
¥43,223 total
includes taxes & fees
May 25 - May 26
The Inn at Chesapeake Bay Beach Club

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.
"Just as one would expect with Hyatt hotel Great food, pool was really nice "
United States
Raymon
The price is ¥37,447
¥49,976 total
includes taxes & fees
May 27 - May 28
Hyatt Regency Chesapeake Bay

The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (41 reviews)
"The luxurious bed and the heated bathroom floor added substantially to our lovely accommodations."
United States
Howard
The price is ¥68,955
¥75,850 total
includes taxes & fees
May 12 - May 13
The Oaks Waterfront

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,007 reviews)
"Property staff were friendly and helpful. Although is an older property, it has a lot of charm. Looking forward to returning after the renovation. Pool is also now open!"
United States
Tatiana
The price is ¥21,010
¥26,455 total
includes taxes & fees
May 12 - May 13
Rod 'N' Reel Resort

The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,004 reviews)
  • cleanliness
    Historic district hotel blends Beaux Arts elegance with spa luxury, featuring lavish treatments near Annapolis attractions.
"Our room was comfortable."
United States
Tracy
The price is ¥28,046
¥31,972 total
includes taxes & fees
May 10 - May 11
The Westin Annapolis

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1,006 reviews)
  • cleanliness
    Upscale Annapolis retreat offers nautical elegance with Egyptian cotton linens and pillowtop beds.
"Room was clean and very comfortable."
United States
Doug
The price is ¥28,685
¥32,700 total
includes taxes & fees
Jun 7 - Jun 8
Graduate by Hilton Annapolis

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (926 reviews)
"Our suite had a great view of luxury yachts and boats!"
United States
Gordon
The price is ¥33,161
¥37,804 total
includes taxes & fees
Jun 7 - Jun 8
Annapolis Waterfront Hotel, Autograph Collection
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.

Top St. Michaels Hotel Reviews

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 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.