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

Our top choices for St. Michaels luxury hotels

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

Inn at Perry Cabin
Downtown St. Michaels
  • Waterfront luxury awaits with golf, spa, and marina at this St. Michaels coastal retreat.
￥67,625
￥74,388 total
includes taxes & fees
Sep 7 - Sep 8
Inn at Perry Cabin
Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen
Luxury Suite, 1 Bedroom, Balcony | Balcony view
Indoor wedding
Luxury Cottage, 1 King Bed, River View | Premium bedding, iron/ironing board, WiFi (free), bed sheets

2. The Oaks Waterfront

The Oaks Waterfront
Easton
￥69,954
￥76,949 total
includes taxes & fees
Aug 26 - Aug 27
The Oaks Waterfront
Reception
Lobby
Bar (on property)
Garden

3. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
￥15,510
￥17,682 total
includes taxes & fees
Aug 30 - Aug 31
DoubleTree by Hilton Hotel Annapolis
Dock
Dock
Porch
Terrace/patio

4. Marvel's on the Creek

Marvel's on the Creek
East New Market
￥29,247
￥32,464 total
includes taxes & fees
Aug 25 - Aug 26
Marvel's on the Creek
Front of property - evening/night
Ballroom
Dining
Garden

5. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
￥34,277
￥42,091 total
includes taxes & fees
Aug 31 - Sep 1
The Inn at Chesapeake Bay Beach Club
View from property
Lobby
Lobby
Lobby

6. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
Annapolis
  • Upscale Annapolis retreat offers nautical elegance with Egyptian cotton linens and pillowtop beds.
￥23,639
￥26,949 total
includes taxes & fees
Aug 30 - Aug 31
Graduate by Hilton Annapolis
Outdoor wedding area
Interior
Coffee shop
Hair salon

7. Rod 'N' Reel Resort

Rod 'N' Reel Resort
Chesapeake Beach
￥16,051
￥23,109 total
includes taxes & fees
Sep 3 - Sep 4
Rod 'N' Reel Resort
Lobby
Property amenity
View from property
Lobby

8. The Westin Annapolis

The Westin Annapolis
Annapolis
  • Historic district hotel blends Beaux Arts elegance with spa luxury, featuring lavish treatments near Annapolis attractions.
￥26,863
￥30,624 total
includes taxes & fees
Aug 30 - Aug 31
The Westin Annapolis
Indoor pool, 2 outdoor pools, pool umbrellas, sun loungers
View from room
Building design
Exterior

9. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
  • Chesapeake Bay resort offers luxury with private beach, full-service spa, and championship golf.
￥33,538
￥45,647 total
includes taxes & fees
Sep 2 - Sep 3
Hyatt Regency Chesapeake Bay
Premium bedding, down comforters, pillowtop beds, in-room safe
Room, 1 King Bed | Premium bedding, down comforters, pillowtop beds, in-room safe
Room, 1 King Bed | Premium bedding, down comforters, pillowtop beds, in-room safe
Exterior

10. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
Historic District
￥34,206
￥38,995 total
includes taxes & fees
Aug 31 - Sep 1
Annapolis Waterfront Hotel, Autograph Collection
View all properties

Top St. Michaels Hotel Reviews

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 less than an hour 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 1 day ago
Country Inn & Suites by Radisson, Annapolis, MD
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 4 days ago
Hyatt Regency Chesapeake Bay
Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"Amazing experience highly recommend"
Andrew 2-night trip
Posted 8 days ago
Inn at Perry Cabin

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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