Find Hotels with Bars in St. Michaels, MD

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Check availability on St. Michaels Hotels with Bars

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!"
$127 nightly
The price is $141
Oct 19 - Oct 20
Total with taxes and fees
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!"
$179 nightly
The price is $197
Nov 2 - Nov 3
Total with taxes and fees
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. "
$218 nightly
The price is $242
Nov 2 - Nov 3
Total with taxes and fees
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"
$239 nightly
The price is $263
Oct 6 - Oct 7
Total with taxes and fees
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."
$549 nightly
The price is $604
Oct 9 - Oct 10
Total with taxes and fees
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."
$211 nightly
The price is $232
Oct 9 - Oct 10
Total with taxes and fees
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!"
$149 nightly
The price is $165
Oct 26 - Oct 27
Total with taxes and fees
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"
$459 nightly
The price is $505
Oct 5 - Oct 6
Total with taxes and fees
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!"
$200 nightly
The price is $220
Nov 2 - Nov 3
Total with taxes and fees
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 !"
$199 nightly
The price is $227
Oct 5 - Oct 6
Total with taxes and fees
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

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.

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