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
Sep 10 - Sep 11
Tomorrow
Sep 11 - Sep 12
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

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.
₩868,320
₩955,152 total
includes taxes & fees
Oct 6 - Oct 7
Inn at Perry Cabin

2. The Oaks Waterfront

The Oaks Waterfront
Easton
₩589,734
₩648,707 total
includes taxes & fees
Sep 13 - Sep 14
The Oaks Waterfront

3. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
₩256,275
₩318,555 total
includes taxes & fees
Sep 28 - Sep 29
The Inn at Chesapeake Bay Beach Club

4. Rod 'N' Reel Resort

Rod 'N' Reel Resort
Chesapeake Beach
₩193,744
₩259,677 total
includes taxes & fees
Oct 1 - Oct 2
Rod 'N' Reel Resort

5. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
  • Chesapeake Bay resort offers luxury with private beach, full-service spa, and championship golf.
₩292,120
₩395,476 total
includes taxes & fees
Sep 29 - Sep 30
Hyatt Regency Chesapeake Bay

6. Marvel's on the Creek

Marvel's on the Creek
East New Market
₩268,000
₩297,480 total
includes taxes & fees
Sep 12 - Sep 13
Marvel's on the Creek

7. The Westin Annapolis

The Westin Annapolis
Annapolis
  • Historic district hotel blends Beaux Arts elegance with spa luxury, featuring lavish treatments near Annapolis attractions.
₩239,860
₩273,440 total
includes taxes & fees
Sep 13 - Sep 14
The Westin Annapolis

8. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
Annapolis
  • Upscale Annapolis retreat offers nautical elegance with Egyptian cotton linens and pillowtop beds.
₩207,673
₩236,748 total
includes taxes & fees
Oct 1 - Oct 2
Graduate by Hilton Annapolis

9. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
Historic District
₩309,808
₩353,181 total
includes taxes & fees
Oct 4 - Oct 5
Annapolis Waterfront Hotel, Autograph Collection

10. The Inn at Tacaro Estate

The Inn at Tacaro Estate
Tracys Landing
  • Indulge in beachside luxury at this 5-star estate featuring a seasonal outdoor pool, private balconies, and Italian Frette sheets.
₩531,484
₩605,891 total
includes taxes & fees
Sep 13 - Sep 14
The Inn at Tacaro Estate
View all properties

Top St. Michaels Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Beautiful inn! Great location! Very clean! The bed and linens were extremely comfortable. Can't wait to stay again!!"
Kathryn 1-night trip
Posted less than an hour ago
Historic Inns of Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Great location"
Boryana 1-night trip
Posted 6 hours ago
Graduate by Hilton Annapolis
St Michaels Inn

St Michaels Inn

8/10 Good
"The staff was very welcoming"
ANA CAROLINA 1-night trip
Posted 20 hours ago
St Michaels Inn
Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"It’s so lovely and elegant I almost don’t want to tell people it’s there. Stunning, perfect in every way."
Susan 1-night trip
Posted 2 days ago
Inn at Perry Cabin
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

8/10 Good
"The staff was top notch. Not everything I have to say is positive but the staff was probably the best I’ve ever had. The room had a few flaws but the front desk, kitchen and housekeeping staff were incredibly friendly and helpful. They always put the guest needs first. I would return here just because of the staff."
David 5-night trip
Posted 2 days ago
Holiday Inn Express & Suites Annapolis by IHG
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

10/10 Excellent
"Would definitely return in the near future. My family had fun."
Abdoul Latif 1-night trip
Posted 5 days ago
Hyatt Regency Chesapeake Bay

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 Higgins Yacht Yard and Marina.

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