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Check availability on St. Michaels Luxury Hotels

Our top choices for St. Michaels luxury hotels

Breakfast, lunch, dinner served; sea views
Inn at Perry Cabin

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (371)
"Friendly and attentive staff, good cleaning services"
United States
Nathan
The price is Rp7.840.022
Rp9.486.460 total
includes taxes & fees
14 Dec - 15 Dec
Inn at Perry Cabin
Garden
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1001)
"Great place!"
United States
Tawnya
The price is Rp1.272.627
Rp1.450.795 total
includes taxes & fees
28 Dec - 29 Dec
DoubleTree by Hilton Hotel Annapolis
Front of property – evening/night
The Inn at Chesapeake Bay Beach Club

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, (429)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
United States
Rery
The price is Rp3.065.809
Rp3.827.285 total
includes taxes & fees
22 Dec - 23 Dec
The Inn at Chesapeake Bay Beach Club
Indoor pool, 2 outdoor pools, pool umbrellas, pool loungers
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
4.0 star property
Cambridge
8.8 out of 10, Excellent, (1002)
"Very courteous staff."
United States
Joseph
The price is Rp2.695.112
Rp3.509.529 total
includes taxes & fees
1 Jan - 2 Jan 2026
Hyatt Regency Chesapeake Bay
Dock
Marvel's on the Creek

Marvel's on the Creek

Marvel's on the Creek
4.0 star property
East New Market
10.0 out of 10, Exceptional, (161)
"Clean & spacious room. Amazing hospitality. Excellent communication!"
United States
Chin
The price is Rp3.335.200
Rp3.702.072 total
includes taxes & fees
24 Dec - 25 Dec
Marvel's on the Creek
Balcony
Rod 'N' Reel Resort

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.4 out of 10, Very good, (1000)
"The hotel is beautiful I can’t wait for"
United States
Lynn
The price is Rp1.773.242
Rp2.301.819 total
includes taxes & fees
11 Jan - 12 Jan 2026
Rod 'N' Reel Resort
Front of property
The Oaks Waterfront

The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (41)
"Loved the Oaks! Fabulous accommodations and excellent staff"
United States
Barbara
The price is Rp6.888.856
Rp7.577.741 total
includes taxes & fees
15 Dec - 16 Dec
The Oaks Waterfront
View from property
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1002)
"Very nice hotel. The dog park could have better lighting. "
United States
Andrew
The price is Rp2.170.274
Rp2.474.112 total
includes taxes & fees
21 Dec - 22 Dec
Graduate by Hilton Annapolis
View from property
The Westin Annapolis

The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1000)
"Spectacular "
United States
Dennis
The price is Rp2.568.104
Rp2.927.638 total
includes taxes & fees
21 Dec - 22 Dec
The Westin Annapolis
Room, 2 Queen Beds, Balcony | Premium bedding, down duvets, pillow-top beds, in-room safe
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (881)
"Great location, nice and clean "
United States
Micah
The price is Rp2.962.491
Rp3.377.241 total
includes taxes & fees
21 Dec - 22 Dec
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.
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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 Town Hall and Saint Michaels Village.