Find Hotels with Bar in Annapolis, MD from CA $100

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Nov 12 - Nov 13
Tomorrow
Nov 13 - Nov 14
This weekend
Nov 13 - Nov 15
Next weekend
Nov 20 - Nov 22

Our top choices for Annapolis hotels with a bar

A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.

1. Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (2,065 reviews)
"Great location, excellent stay"
United States
Christiaan
The price is CA $100
CA $163 total
includes taxes & fees
Dec 13 - Dec 14
Historic Inns of Annapolis
A spacious atrium with a high ceiling, skylights, and a patterned floor.

2. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.2 out of 10, Wonderful, (1,014 reviews)
"Brunch was the best we had the whole trip! Excellent food and wonderful staff."
United States
REBECCA
The price is CA $185
CA $211 total
includes taxes & fees
Nov 29 - Nov 30
Graduate by Hilton Annapolis
A modern lounge area with a sofa, chairs, a coffee table, and a bookshelf.

3. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,010 reviews)
"Great location, friendly staff."
United States
Joel
The price is CA $139
CA $159 total
includes taxes & fees
Nov 22 - Nov 23
Hilton Garden Inn Annapolis Downtown
A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.

4. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,276 reviews)
"i enjoyed how close the place was to many local shops and resturants."
United States
michel demanche
The price is CA $127
CA $145 total
includes taxes & fees
Nov 29 - Nov 30
DoubleTree by Hilton Hotel Annapolis
A swimming pool with a clear blue water, surrounded by lounge chairs and a glass wall.

5. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1,015 reviews)
"Great location"
United States
Jose
The price is CA $146
CA $167 total
includes taxes & fees
Dec 13 - Dec 14
Crowne Plaza Annapolis by IHG
A modern lobby with a reception desk, seating area, and potted plants.

6. Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very good, (1,000 reviews)
"The room was clean, the staff were wonderful, we didn't do breakfast and we were charged $8.00 a day for parking."
United States
Walter
The price is CA $119
CA $135 total
includes taxes & fees
Nov 22 - Nov 23
Hilton Garden Inn Annapolis
A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.

7. The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,000 reviews)
"Excellent location, Very nice Hotel"
United States
Loraine
The price is CA $227
CA $258 total
includes taxes & fees
Nov 15 - Nov 16
The Westin Annapolis
An outdoor patio with tables, chairs, and a fire feature.

8. Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
3.0 star property
Annapolis
8.8 out of 10, Excellent, (250 reviews)
"Nice hotel"
United States
Imola
The price is CA $180
CA $205 total
includes taxes & fees
Nov 17 - Nov 18
Fairfield Inn & Suites By Marriott Annapolis
A balcony with a table set for two, overlooking a marina with boats.

9. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (1,001 reviews)
"Staff was Great, Great Location. Nice Restaurant Bartender was great!"
United States
Donna
The price is CA $305
CA $348 total
includes taxes & fees
Dec 7 - Dec 8
Annapolis Waterfront Hotel, Autograph Collection
An outdoor patio with tables, chairs, and a fire feature.

10. Residence Inn By Marriott Annapolis

Residence Inn By Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (95 reviews)
"Amazing stay!"
United States
Caitlin
The price is CA $192
CA $218 total
includes taxes & fees
Nov 29 - Nov 30
Residence Inn By Marriott Annapolis
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 Annapolis Hotel Reviews

A two-story house with a porch, a front door, and a small garden area.
The Wildset

The Wildset

The Wildset
Downtown St. Michaels

10/10 Excellent

Our stay at the Wildset was amazing! The room was beautiful and clean. The staff were available at all hours and did the most to ensure our stay was special. The hotel has lots of small touches that truly make the experience like bikes, a cafe with coffee and drinks, and smore's kits in the evenings.
Canada
Mairi
Reviewed August 11, 2026
The Wildset

Frequently Asked Questions

Searching for hotels with bars in Annapolis?

If you prefer a place to stay where you can enjoy a beer after sightseeing, Annapolis offers 554 properties, including 12 accommodations with an onsite bar. While you’re here, you can check out Maryland State House and William Paca House.

What are the best hotels with bars in Annapolis?

Here are some of the top Annapolis accommodations with bars: Crowne Plaza Annapolis by IHG: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Historic Inns of Annapolis: Enjoy the bar, free WiFi, and room service. DoubleTree by Hilton Hotel Annapolis: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Hilton Garden Inn Annapolis Downtown: Hotel with restaurant. Enjoy the bar, free WiFi, and breakfast. Graduate by Hilton Annapolis: Hotel with restaurant. Enjoy the bar, free WiFi, and breakfast.

How many hotels with bars on site are there in Annapolis?

Expedia has 12 hotels with a bar in Annapolis.

What is there to do in Annapolis?

To experience the area's highlights, consider visiting Maryland State House, William Paca House, and Annapolis City Dock, and then find a cozy spot for a nightcap. Other places to see include Navy-Marine Corps Memorial Stadium and Maryland Hall for Creative Arts. Annapolis is recognized for its college campus, array of shops, and top-notch restaurants.

When is the best time to visit Annapolis?

Visiting local bars in Annapolis is better when you know what the weather holds. These temperatures and rainfall averages can help you decide 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 40°F. Average annual precipitation for Annapolis is 52 inches.

How can I get to Annapolis and around the area?

You might want to make the most of these transportation options in and around Annapolis: Fly into Fort Meade, MD (FME-Tipton), which is located 16.2 mi (26.1 km) from the heart of the city. Otherwise, you can search for flights to Baltimore Washington Intl. Airport (BWI), which is 16.8 mi (27 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

Explore a world of travel with Expedia