Find Hotels with Bars in St. Michaels, MD

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Top St. Michaels Hotels with Bars

Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (903)
"The BEAUTIFUL backyard on the water, the walking trail, and the walkability to several restaurants were so nice!"
The price is SAR 476
SAR 529 total
includes taxes & fees
19 Oct - 20 Oct
Holiday Inn Express Annapolis East-Kent Island by IHG
The Tidewater Inn
Terrace/patio

The Tidewater Inn

3.0 star property
8.8 out of 10, Excellent, (830)
"Great place - our third stay!"
The price is SAR 671
SAR 738 total
includes taxes & fees
2 Nov - 3 Nov
The Tidewater Inn
The Inn at Chesapeake Bay Beach Club
Front of property - evening/night

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (420)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
The price is SAR 731
SAR 907 total
includes taxes & fees
2 Nov - 3 Nov
The Inn at Chesapeake Bay Beach Club
The Wildset
Premium Room | Frette Italian sheets, premium bedding, iron/ironing board, free WiFi

The Wildset

2.5 star property
9.8 out of 10, Exceptional, (382)
"fantastic location, great bouboun selection at the bar and wonderful staff"
The price is SAR 821
SAR 986 total
includes taxes & fees
6 Oct - 7 Oct
The Wildset
Inn at Perry Cabin
Breakfast, lunch, dinner served; ocean views

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (364)
"Beautiful place to stay."
The price is SAR 1,873
SAR 2,267 total
includes taxes & fees
9 Oct - 10 Oct
Inn at Perry Cabin
Wylder Tilghman Island
Seasonal outdoor pool

Wylder Tilghman Island

2.0 star property
8.8 out of 10, Excellent, (81)
"Very relaxing stay."
The price is SAR 641
SAR 870 total
includes taxes & fees
12 Oct - 13 Oct
Wylder Tilghman Island
Hyatt Place Kent Narrows & Marina
Terrace/patio

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (633)
"Great location and rooms. Great place!"
The price is SAR 559
SAR 620 total
includes taxes & fees
26 Oct - 27 Oct
Hyatt Place Kent Narrows & Marina
The Oaks Waterfront
Front of property

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (38)
"Loved the Oaks! Fabulous accommodations and excellent staff"
The price is SAR 1,549
SAR 1,704 total
includes taxes & fees
5 Oct - 6 Oct
The Oaks Waterfront
The Tilghman Island Inn
Outdoor banquet area

The Tilghman Island Inn

3.5 star property
9.6 out of 10, Exceptional, (111)
"Great staff and food!"
The price is SAR 750
SAR 825 total
includes taxes & fees
2 Nov - 3 Nov
The Tilghman Island Inn
Anchored Inn at Hidden Harbour Marina
Front of property

Anchored Inn at Hidden Harbour Marina

2.5 star property
9.4 out of 10, Exceptional, (456)
"The view from the balcony is the best, whether at night or the day time. The outside bar everyone is so friendly. I have stayed here a few times and every time I come to the area, I will only stay here. I highly recommend it !"
The price is SAR 672
SAR 766 total
includes taxes & fees
5 Oct - 6 Oct
Anchored Inn at Hidden Harbour Marina
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.
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Top St. Michaels Hotel Reviews

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"Great"
BRIAN 2-night trip
Posted 3 days ago
Hilton Garden Inn Annapolis Downtown

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Explore a world of travel with Expedia

Frequently asked questions

Searching for hotels with bars in St. Michaels?
St. Michaels features 66 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: The Wildset: Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi. Inn at Perry Cabin: Hotel with restaurant. Enjoy the 2 bars, free WiFi, and free valet parking.
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 St. Michaels Museum and Saint Michaels Village. 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.