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

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Check availability on St. Michaels Luxury Hotels

Tonight
Aug 25 - Aug 26
Tomorrow
Aug 26 - Aug 27
This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

Our top choices for St. Michaels luxury hotels

A room with a view of a wooden deck and a gazebo by the water.
A golf course with a water hazard and surrounding trees.
A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.
A hotel room with a large bed, a chair, a desk, and a television.

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.
NT$14,168
NT$15,584 total
includes taxes & fees
Sep 7 - Sep 8
Inn at Perry Cabin
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.
A deck with wicker furniture, a table, and an umbrella, overlooking a lake with trees and a dock.
A wooden console table with framed floral artwork, two lamps, and two ottomans.
A banquet hall with round tables set for dining, large windows with a view of a lake, and white chairs.

2. The Oaks Waterfront

The Oaks Waterfront
Easton
NT$14,021
NT$15,423 total
includes taxes & fees
Aug 26 - Aug 27
The Oaks Waterfront
A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.
A modern living room with a sofa, armchairs, a coffee table, and a fireplace.
A DoubleTree by Hilton hotel entrance with a brick facade, a gated driveway, and a clear sky.
A spacious lobby with a high ceiling, a central seating area with sofas and tables, and large windows with curtains.

3. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
NT$3,109
NT$3,544 total
includes taxes & fees
Aug 30 - Aug 31
DoubleTree by Hilton Hotel Annapolis
A wooden dock with a bench and a wooden post with a light fixture.
A wooden dock leading to a house with a lawn and a pond.
A corner room with a window overlooking a green field, a wooden barrel, a chair, and a small table with a candle and flowers.
A fire pit surrounded by two white chairs with blue cushions, a small table, and potted plants.

4. Marvel's on the Creek

Marvel's on the Creek
East New Market
NT$6,372
NT$7,073 total
includes taxes & fees
Aug 26 - Aug 27
Marvel's on the Creek
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.
A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.

5. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
NT$6,113
NT$7,596 total
includes taxes & fees
Sep 8 - Sep 9
The Inn at Chesapeake Bay Beach Club
A marina with numerous boats docked, a prominent building with a dome in the background, and a clear view of the water.
A spacious atrium with a high ceiling, skylights, and a patterned floor.
A hotel lobby with a high ceiling, large windows, and a blue and white color scheme. Tables and chairs are arranged for dining or meetings.
A bar with a brick wall, a mounted shark, and various bottles and glasses on shelves.

6. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
Annapolis
  • Upscale Annapolis retreat offers nautical elegance with Egyptian cotton linens and pillowtop beds.
NT$4,956
NT$5,649 total
includes taxes & fees
Aug 30 - Aug 31
Graduate by Hilton Annapolis
A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.
A modern salon with multiple black salon chairs, a white reception desk, and large windows allowing natural light.
A staircase with a wooden handrail, a blue wall, and a ceiling light fixture.
A restaurant with a high ceiling, large windows, and a central bar area.

7. Rod 'N' Reel Resort

Rod 'N' Reel Resort
Chesapeake Beach
NT$3,144
NT$4,551 total
includes taxes & fees
Sep 3 - Sep 4
Rod 'N' Reel Resort
A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.
A store with shelves of beverages, a counter with a cash register, and baskets with items.
A modern hotel lobby with a curved seating area, a bar, and a large bookshelf.
A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.

8. The Westin Annapolis

The Westin Annapolis
Annapolis
  • Historic district hotel blends Beaux Arts elegance with spa luxury, featuring lavish treatments near Annapolis attractions.
NT$5,384
NT$6,138 total
includes taxes & fees
Aug 30 - Aug 31
The Westin Annapolis
An indoor swimming pool with lounge chairs and tables, large windows, and a high wooden ceiling.
A marina with boats docked, a sandy beach, and a clear blue sky.
A spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.
A marina with boats docked, a large building with a tower in the background, and a dock extending into the water.

9. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
  • Chesapeake Bay resort offers luxury with private beach, full-service spa, and championship golf.
NT$6,470
NT$8,864 total
includes taxes & fees
Sep 2 - Sep 3
Hyatt Regency Chesapeake Bay
A balcony with a table set for two, overlooking a marina with boats.
A hotel room with a large bed, a chair, a small table, and a view of a body of water.
A waterfront property with a docked boat, a tall building with balconies, and a church spire in the background.
The exterior of the Annapolis Waterfront Hotel with a clear entrance, large windows, and a bench outside.

10. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
Historic District
NT$6,601
NT$7,525 total
includes taxes & fees
Aug 31 - Sep 1
Annapolis Waterfront Hotel, Autograph Collection
View all properties

Top St. Michaels Hotel Reviews

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 10 hours ago
Crowne Plaza Annapolis by IHG
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"The beds were so comfortable"
christopher 1-night trip
Posted 11 hours ago
The Westin Annapolis
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Room was clean, staff was great. They should have notified in advance or had on line about all the construction and pool being closed."
Rick 1-night trip
Posted 15 hours ago
St Michaels Inn
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 2 days 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 4 days ago
Holiday Inn Express & Suites 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 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 Saint Michaels Town Hall.

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