The Best Luxury Hotels in St. Michaels, MD from ￥14,850 in 2026

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

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Our top choices for St. Michaels luxury hotels

Premium bedding, down comforters, in-room safe, desk

Suite, 1 Bedroom (Water View) | Premium bedding, down comforters, in-room safe, desk

1. Inn at Perry Cabin

Downtown St. Michaels

Waterfront luxury awaits with golf, spa, and marina at this St. Michaels coastal retreat.

￥99,539

￥109,493 total

includes taxes & fees

Oct 6 - Oct 7

Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen

Luxury Cottage, 1 King Bed, River View | Premium bedding, iron/ironing board, WiFi (free), bed sheets

Luxury Suite, 1 Bedroom, Balcony | Balcony view

2. The Oaks Waterfront

Easton

￥67,604

￥74,364 total

includes taxes & fees

Sep 14 - Sep 15

3. DoubleTree by Hilton Hotel Annapolis

Annapolis

￥12,805

￥14,597 total

includes taxes & fees

Sep 27 - Sep 28

4. Marvel's on the Creek

East New Market

￥28,408

￥31,532 total

includes taxes & fees

Sep 21 - Sep 22

5. The Inn at Chesapeake Bay Beach Club

Stevensville

￥29,527

￥36,702 total

includes taxes & fees

Sep 28 - Sep 29

6. Rod 'N' Reel Resort

Chesapeake Beach

￥21,321

￥28,782 total

includes taxes & fees

Oct 1 - Oct 2

7. Graduate by Hilton Annapolis

Annapolis

Upscale Annapolis retreat offers nautical elegance with Egyptian cotton linens and pillowtop beds.

￥23,806

￥27,139 total

includes taxes & fees

Oct 1 - Oct 2

Seasonal outdoor pool, pool umbrellas, sun loungers

Taylor's Suite | Frette Italian sheets, premium bedding, down comforters, WiFi (free)

8. 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.

￥58,787

￥67,017 total

includes taxes & fees

Sep 13 - Sep 14

View all properties

Top St. Michaels Hotel Reviews

Hilton Garden Inn Annapolis Downtown

8/10 Good

"Not able to stream TV. Uncomfortable bed and bedding was noticeably worn"

Graduate by Hilton Annapolis

10/10 Excellent

"Great stay- Go Navy Beat Army!"

St Michaels Inn

8/10 Good

"There was a glitch after sign in. We were locked out of our room and informed to come to the office immediately. When we went to the desk we were informed we'd been given the wrong room. We received new door cards and stayed in the same room and other guests had their room changed. The issue came up again at check-out. It is a nice hotel with many updates."

DoubleTree by Hilton Hotel Annapolis

8/10 Good

"The room was clean and comfortable, however when i went to check out the élévator on my floor was n"

Crowne Plaza Annapolis by IHG

10/10 Excellent

"All good."

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."

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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Treat yourself

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Check availability on St. Michaels Luxury Hotels

Our top choices for St. Michaels luxury hotels

1. Inn at Perry Cabin

2. The Oaks Waterfront

3. DoubleTree by Hilton Hotel Annapolis

4. Marvel's on the Creek

5. The Inn at Chesapeake Bay Beach Club

6. Rod 'N' Reel Resort

7. Graduate by Hilton Annapolis

8. The Inn at Tacaro Estate

9. The Westin Annapolis

10. Hyatt Regency Chesapeake Bay

Top St. Michaels Hotel Reviews

Hilton Garden Inn Annapolis Downtown

Graduate by Hilton Annapolis

St Michaels Inn

DoubleTree by Hilton Hotel Annapolis

Crowne Plaza Annapolis by IHG

Inn at Perry Cabin

Frequently asked questions

Explore a world of travel with Expedia

Find Luxury Hotels in St. Michaels, MD

Change your mind

Treat yourself

Be picky

Check availability on St. Michaels Luxury Hotels

Our top choices for St. Michaels luxury hotels

1. Inn at Perry Cabin

2. The Oaks Waterfront

3. DoubleTree by Hilton Hotel Annapolis

4. Marvel's on the Creek

5. The Inn at Chesapeake Bay Beach Club

6. Rod 'N' Reel Resort

7. Graduate by Hilton Annapolis

8. The Inn at Tacaro Estate

9. The Westin Annapolis

10. Hyatt Regency Chesapeake Bay

Top St. Michaels Hotel Reviews

Hilton Garden Inn Annapolis Downtown

Graduate by Hilton Annapolis

St Michaels Inn

DoubleTree by Hilton Hotel Annapolis

Crowne Plaza Annapolis by IHG

Inn at Perry Cabin

Frequently asked questions

Explore a world of travel with Expedia