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

Find Luxury Hotels in St. Michaels, MD

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Check availability on St. Michaels Luxury Hotels

Tonight
Aug 22 - Aug 23
Tomorrow
Aug 23 - Aug 24
Next weekend
Aug 28 - Aug 30
In two weeks
Sep 4 - Sep 6

Our top choices for St. Michaels luxury hotels

1. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
  • Waterfront luxury awaits with golf, spa, and marina at this St. Michaels coastal retreat.
₩589,601
₩648,561 total
includes taxes & fees
Sep 7 - Sep 8
Inn at Perry Cabin

2. The Oaks Waterfront

The Oaks Waterfront
Easton
₩609,904
₩670,894 total
includes taxes & fees
Sep 7 - Sep 8
The Oaks Waterfront

3. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
₩136,075
₩155,125 total
includes taxes & fees
Aug 30 - Aug 31
DoubleTree by Hilton Hotel Annapolis

4. Marvel's on the Creek

Marvel's on the Creek
East New Market
₩277,166
₩307,654 total
includes taxes & fees
Aug 23 - Aug 24
Marvel's on the Creek

5. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
₩300,720
₩369,276 total
includes taxes & fees
Aug 31 - Sep 1
The Inn at Chesapeake Bay Beach Club

6. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
Annapolis
  • Upscale Annapolis retreat offers nautical elegance with Egyptian cotton linens and pillowtop beds.
₩207,390
₩236,425 total
includes taxes & fees
Aug 30 - Aug 31
Graduate by Hilton Annapolis

7. Rod 'N' Reel Resort

Rod 'N' Reel Resort
Chesapeake Beach
₩147,218
₩209,849 total
includes taxes & fees
Sep 3 - Sep 4
Rod 'N' Reel Resort

8. The Westin Annapolis

The Westin Annapolis
Annapolis
  • Historic district hotel blends Beaux Arts elegance with spa luxury, featuring lavish treatments near Annapolis attractions.
₩235,671
₩268,665 total
includes taxes & fees
Aug 30 - Aug 31
The Westin Annapolis

9. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
  • Chesapeake Bay resort offers luxury with private beach, full-service spa, and championship golf.
₩294,240
₩400,481 total
includes taxes & fees
Sep 3 - Sep 4
Hyatt Regency Chesapeake Bay

10. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
Historic District
₩288,940
₩329,391 total
includes taxes & fees
Aug 30 - Aug 31
Annapolis Waterfront Hotel, Autograph Collection
View all properties

Top St. Michaels Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Great location nicely appointed room, great paintings"
Pauline 1-night trip
Posted 7 hours ago
Historic Inns of Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Great staff everywhere on the property."
Fabiana 1-night trip
Posted 11 hours ago
DoubleTree by Hilton Hotel Annapolis
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"A"
Wayne 1-night trip
Posted 13 hours ago
Country Inn & Suites by Radisson, Annapolis, MD
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

10/10 Excellent
"Perfect for what I needed"
Andrew 1-night trip
Posted 16 hours ago
Holiday Inn Express & Suites Annapolis by IHG
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Rooms where clean, staff was nice"
Debra 1-night trip
Posted 1 day ago
Crowne Plaza Annapolis by IHG
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

10/10 Excellent
"Excellent well-maintained rooms with new ceiling fan. Summer amenities are geared to families and include mini golf, multiple pools indoors & outdoors, day spa, convenience shop with coffee , pool tables (although not as well maintained as other areas of the property), walking paths, and a regulationgolf course. Families can be quite boisterous; we will opt for calmer winter months in future."
Annette 2-night trip
Posted 1 day ago
Hyatt Regency Chesapeake Bay
Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"Amazing experience highly recommend"
Andrew 2-night trip
Posted 6 days 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 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.

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