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

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Check availability on St. Michaels Luxury Hotels

This weekend
10 Jul - 12 Jul
Next weekend
17 Jul - 19 Jul

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, (391 reviews)
  • cleanliness
    Waterfront luxury awaits with golf, spa, and marina at this St. Michaels coastal retreat.
The price is ฿22,163
฿24,379 total
includes taxes & fees
23 Jul - 24 Jul
Inn at Perry Cabin
Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen

The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (42 reviews)
The price is ฿14,646
฿16,110 total
includes taxes & fees
19 Jul - 20 Jul
The Oaks Waterfront
Reception

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1,027 reviews)
The price is ฿3,443
฿3,925 total
includes taxes & fees
12 Jul - 13 Jul
DoubleTree by Hilton Hotel Annapolis
Seasonal outdoor pool, pool umbrellas, pool loungers

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.6 out of 10, Exceptional, (17 reviews)
  • cleanliness
    Indulge in beachside luxury at this 5-star estate featuring a seasonal outdoor pool, private balconies, and Italian Frette sheets.
The price is ฿11,331
฿12,918 total
includes taxes & fees
15 Jul - 16 Jul
The Inn at Tacaro Estate
Indoor pool, 2 outdoor pools, pool umbrellas, pool loungers

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
4.0 star property
Cambridge
8.8 out of 10, Excellent, (1,003 reviews)
  • cleanliness
    Chesapeake Bay resort offers luxury with private beach, full-service spa, and championship golf.
The price is ฿9,974
฿12,912 total
includes taxes & fees
11 Jul - 12 Jul
Hyatt Regency Chesapeake Bay
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 ฿7,526
฿9,203 total
includes taxes & fees
4 Aug - 5 Aug
The Inn at Chesapeake Bay Beach Club
Outdoor wedding area

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,012 reviews)
The price is ฿6,354
฿8,164 total
includes taxes & fees
15 Jul - 16 Jul
Rod 'N' Reel Resort
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 ฿6,656
฿7,388 total
includes taxes & fees
14 Jul - 15 Jul
Marvel's on the Creek
Lobby lounge

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.
The price is ฿5,971
฿6,807 total
includes taxes & fees
26 Jul - 27 Jul
The Westin Annapolis
View from property

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1,007 reviews)
  • cleanliness
    Upscale Annapolis retreat offers nautical elegance with Egyptian cotton linens and pillowtop beds.
The price is ฿6,029
฿6,873 total
includes taxes & fees
26 Jul - 27 Jul
Graduate by Hilton 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.
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Top St. Michaels Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Great location. Check in was a bit confusing since it was at a different property. Otherwise a great stay!"
Peter 1-night trip
Posted 6 hours ago
Historic Inns of Annapolis

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 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.