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 26 - Aug 27
Tomorrow
Aug 27 - Aug 28
This weekend
Aug 28 - Aug 30
Next weekend
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.
¥70,764
¥77,840 total
includes taxes & fees
Sep 7 - Sep 8
Inn at Perry Cabin

2. The Oaks Waterfront

The Oaks Waterfront
Easton
¥70,016
¥77,018 total
includes taxes & fees
Sep 24 - Sep 25
The Oaks Waterfront

3. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
¥15,535
¥17,710 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
¥29,591
¥32,846 total
includes taxes & fees
Aug 27 - Aug 28
Marvel's on the Creek

5. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
¥30,549
¥37,958 total
includes taxes & fees
Sep 8 - Sep 9
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.
¥24,752
¥28,217 total
includes taxes & fees
Aug 30 - Aug 31
Graduate by Hilton Annapolis

7. Rod 'N' Reel Resort

Rod 'N' Reel Resort
Chesapeake Beach
¥15,700
¥22,725 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.
¥26,886
¥30,651 total
includes taxes & fees
Sep 6 - Sep 7
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.
¥32,318
¥44,275 total
includes taxes & fees
Sep 2 - Sep 3
Hyatt Regency Chesapeake Bay

10. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
Historic District
¥34,236
¥39,029 total
includes taxes & fees
Sep 2 - Sep 3
Annapolis Waterfront Hotel, Autograph Collection
View all properties

Top St. Michaels Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

8/10 Good
"Location was excellent. A little confusing to check in at another location, and parking was also a bit confusing."
Joseph A 1-night trip
Posted 1 hour ago
Historic Inns of Annapolis
St Michaels Inn

St Michaels Inn

8/10 Good
"This is a typical motel. The room seemed to just have been upgraded in the past 6 months or so. Room had fresh paint, and new vinyl plank flooring. I also believe that our king bed as a newer mattress. The furniture was in good condition but the lamps seemed to be original 50's style. The bathroom still had the original tub/shower with an upgraded shower head. The toilet was most likely original too and very low; as a senor citizen it was so low that it was harder to get up. The sink and marble counter were outside of the bathroom and a nice touch although the two big mirrors must b original since they both has part of the silver coating on the back lower edge eroded by moisture. The breakfast was pitiful; waffle iron and batter machine were in place but not being used. Same for the two-section heated server that was supposed to possible have scrambled eggs and maybe sausage but they were not used either. Thus there were muffins, bangles, and serial. Still in the St. Michaels area and at the priced charged, one could not do much better."
Bill 1-night trip
Posted 20 hours ago
St Michaels Inn
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"I arrived late following a long-distance sailboat race across the Chesapeake Bay. “Nick” was managing the front desk. He was polite, efficient, friendly, and professional. He offered me the best room the hotel had available at my price, and guaranteed I would have a good night’s rest. He was 100% correct. The room was clean and comfortable, and more importantly it was quiet. Check out was easy the next morning."
maurice 1-night trip
Posted 1 day ago
Graduate by Hilton Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

8/10 Good
"I wish I could give half stars because this place is really a 4.5 stars. First off this place was great, it is everything you need for a hotel. Great prices, friendly staff, very clean, very nice hotel. Why I gave it 4 stars? The coffee machine was down for our first night, the jacuzzi was down for maintenance, the wifi went for maintenance lol so it was a little much but I know you can't always control those things. Another small thing, I also wish the TV's were smart TV's and I wish the rooms came with a microwave. Overall great hotel, would stay here again."
Joseph 3-night trip
Posted 2 days ago
Crowne Plaza Annapolis by IHG
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

8/10 Good
"There wasn’t a fan in the bathroom. Very good location in Annapolis."
Tracie 1-night trip
Posted 3 days ago
Country Inn & Suites by Radisson, Annapolis, MD

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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