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

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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, (391 reviews)
  • cleanliness
    Waterfront luxury awaits with golf, spa, and marina at this St. Michaels coastal retreat.
The price is ฿22,301
฿24,531 total
includes taxes & fees
2 Aug - 3 Aug
Inn at Perry Cabin

The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (42 reviews)
The price is ฿14,737
฿16,210 total
includes taxes & fees
19 Jul - 20 Jul
The Oaks Waterfront

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 ฿11,402
฿12,998 total
includes taxes & fees
22 Jul - 23 Jul
The Inn at Tacaro Estate

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
4.0 star property
Cambridge
8.8 out of 10, Excellent, (1,014 reviews)
  • cleanliness
    Chesapeake Bay resort offers luxury with private beach, full-service spa, and championship golf.
The price is ฿10,581
฿13,607 total
includes taxes & fees
28 Jul - 29 Jul
Hyatt Regency Chesapeake Bay

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,001 reviews)
The price is ฿6,378
฿8,195 total
includes taxes & fees
30 Jul - 31 Jul
Rod 'N' Reel Resort

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 ฿6,697
฿7,434 total
includes taxes & fees
16 Jul - 17 Jul
Marvel's on the Creek

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 ฿7,888
฿9,608 total
includes taxes & fees
3 Aug - 4 Aug
The Inn at Chesapeake Bay Beach Club

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (945 reviews)
The price is ฿6,635
฿7,563 total
includes taxes & fees
26 Jul - 27 Jul
Annapolis Waterfront Hotel, Autograph Collection

The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Historic district hotel blends Beaux Arts elegance with spa luxury, featuring lavish treatments near Annapolis attractions.
The price is ฿6,664
฿7,596 total
includes taxes & fees
19 Jul - 20 Jul
The Westin Annapolis

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1,022 reviews)
The price is ฿3,844
฿4,382 total
includes taxes & fees
29 Jul - 30 Jul
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.

Top St. Michaels Hotel Reviews

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.