Find Hotels with Bars in St. Michaels, MD

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Check availability on St. Michaels Hotels with Bars

Our top choices for St. Michaels hotels with a bar

Front of property
The Wildset

The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (408)
"Awesome! Love the room and fireplace!"
United States
Brian
The price is AED 731
AED 885 total
includes taxes & fees
18 Dec - 19 Dec
The Wildset
Breakfast, lunch, dinner served; ocean views
Inn at Perry Cabin

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (371)
"Friendly and attentive staff, good cleaning services"
United States
Nathan
The price is AED 1,783
AED 2,157 total
includes taxes & fees
18 Dec - 19 Dec
Inn at Perry Cabin
Outdoor wedding area
Rod 'N' Reel Resort

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.4 out of 10, Very Good, (1000)
"The hotel is beautiful I can’t wait for"
United States
Lynn
The price is AED 391
AED 507 total
includes taxes & fees
2 Jan - 3 January 2026
Rod 'N' Reel Resort
Lobby
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1007)
"Great value for stay with breakfast included "
United States
Aisling
The price is AED 291
AED 332 total
includes taxes & fees
28 Dec - 29 Dec
Hilton Garden Inn Annapolis Downtown
Reception
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1003)
"Great place!"
United States
Tawnya
The price is AED 280
AED 319 total
includes taxes & fees
28 Dec - 29 Dec
DoubleTree by Hilton Hotel Annapolis
Meeting facility
Historic Inns of Annapolis

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1898)
"Great staff, comfortable beds, clean rooms and perfect location "
United States
Dawn
Historic Inns of Annapolis
Exterior
Wylder Tilghman Island

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (90)
"Very relaxing stay."
United States
Anne
The price is AED 496
AED 707 total
includes taxes & fees
8 Jan - 9 January 2026
Wylder Tilghman Island
Front of property
Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (470)
"Beautiful place to stay, we stay their one to two times a year."
United States
Marjorie
The price is AED 493
AED 561 total
includes taxes & fees
8 Jan - 9 January 2026
Anchored Inn at Hidden Harbour Marina
Indoor pool
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1000)
"Excellent from check in to check out, highly recommend!"
United States
Eric
The price is AED 474
AED 540 total
includes taxes & fees
28 Dec - 29 Dec
Crowne Plaza Annapolis by IHG
Indoor pool, 2 outdoor pools, pool umbrellas, sun loungers
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
4.0 star property
Cambridge
8.8 out of 10, Excellent, (1002)
"Very courteous staff."
United States
Joseph
The price is AED 593
AED 772 total
includes taxes & fees
1 Jan - 2 January 2026
Hyatt Regency Chesapeake Bay
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

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"This is a very nice hotel clean and seems to be new"
richard 1-night trip
Posted 1 day ago
Crowne Plaza Annapolis by IHG

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Frequently asked questions

Searching for hotels with bars in St. Michaels?
St. Michaels features 65 hotels and other accommodations to choose from, and likely many will have a bar where you can unwind with a late-night cocktail. While you're here, consider a visit to St. Michaels Marina and Chesapeake Bay Maritime Museum.
What are the best hotels with bars in St. Michaels?
Here's some of the top St. Michaels hotels with bars: Inn at Perry Cabin: Hotel with restaurant. Enjoy the 2 bars, free WiFi, and free valet parking. The Wildset: Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi.
What is there to do in St. Michaels?
If you have time to explore, consider visiting St. Michaels Marina, Chesapeake Bay Maritime Museum, and St. Michaels Winery, and then find a cozy spot for a nightcap. Other places to see include Saint Michaels Village and Saint Michaels Town Hall. St. Michaels is known for its seafood restaurants, waterfront, and shops.
When is the best time to visit St. Michaels?
Visiting local bars in St. Michaels is more fun in good weather. These rainfall averages and temperatures can help you determine the best time for bar hopping. 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.
How can I get to St. Michaels and around the area?
You might want to make the most of these transportation options in and around St. Michaels: Fly into Easton, MD (ESN-Easton - Newnam), which is located 8.8 mi (14.1 km) away from the heart of the city. You can also search for flights into Fort Meade, MD (FME-Tipton), which is 35.5 mi (57.2 km) away. If you'd like to explore around the area, you may want a rental car for your journey.