Aerial panorama of shipyard and lighthouse in St. Michaels harbor in Maryland in the Chesapeake Bay

Luxury Hotels & Resorts in St. Michaels from NZ$223

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on St. Michaels Luxury Hotels

Our top choices for St. Michaels luxury hotels

Breakfast, lunch, dinner and brunch served

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (390 reviews)
  • cleanliness
    Waterfront luxury awaits with golf, spa, and marina at this St. Michaels coastal retreat.
The price is NZ$1,176
includes taxes & fees
21 June - 22 June
Inn at Perry Cabin
Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen

The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (41 reviews)
The price is NZ$833
includes taxes & fees
14 June - 15 June
The Oaks Waterfront
Indoor pool, 2 outdoor pools, pool umbrellas, pool loungers

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
4.0 star property
Cambridge
8.8 out of 10, Excellent, (1,007 reviews)
  • cleanliness
    Chesapeake Bay resort offers luxury with private beach, full-service spa, and championship golf.
The price is NZ$686
includes taxes & fees
6 July - 7 July
Hyatt Regency Chesapeake Bay
Dock

Marvel's on the Creek

Marvel's on the Creek
4.0 star property
East New Market
10.0 out of 10, Exceptional, (166 reviews)
The price is NZ$348
includes taxes & fees
12 June - 13 June
Marvel's on the Creek
Seasonal outdoor pool, pool umbrellas, pool loungers

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.6 out of 10, Exceptional, (15 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 NZ$625
includes taxes & fees
11 June - 12 June
The Inn at Tacaro Estate
Outdoor wedding area

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 NZ$328
includes taxes & fees
23 June - 24 June
Rod 'N' Reel Resort
Reception

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,015 reviews)
The price is NZ$218
includes taxes & fees
21 June - 22 June
DoubleTree by Hilton Hotel Annapolis
Front of property – evening/night

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, (457 reviews)
The price is NZ$475
includes taxes & fees
15 June - 16 June
The Inn at Chesapeake Bay Beach Club
Premium bedding, down duvets, pillow-top beds, in-room safe

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (936 reviews)
The price is NZ$499
includes taxes & fees
2 July - 3 July
Annapolis Waterfront Hotel, Autograph Collection
View from property

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1,006 reviews)
  • cleanliness
    Upscale Annapolis retreat offers nautical elegance with Egyptian cotton linens and pillowtop beds.
The price is NZ$354
includes taxes & fees
5 July - 6 July
Graduate by Hilton 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.
View all properties

Top St. Michaels Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"The room was spotless and the staff was very helpful and courteous.. hotel was very quiet and comfortable"
Lindsey 3-night trip
Posted 5 hours ago
Country Inn & Suites by Radisson, Annapolis, MD

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.