Find Hotels with Bars in Shady Side, MD

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Check availability on Shady Side Hotels with Bars

Our top choices for Shady Side hotels with a bar

Balcony
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
$136 nightly
The price is $149
Dec 21 - Dec 22
Total with taxes and fees
Rod 'N' Reel Resort
Garden
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, (1002)
"Great place!"
United States
Tawnya
$76 nightly
The price is $87
Dec 28 - Dec 29
Total with taxes and fees
DoubleTree by Hilton Hotel Annapolis
Suite, 1 Bedroom, Terrace | Living area | 42-inch LED TV with digital channels, TV
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
$79 nightly
The price is $90
Dec 21 - Dec 22
Total with taxes and fees
Hilton Garden Inn Annapolis Downtown
Seasonal outdoor pool
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
$175 nightly
The price is $193
Jan 1 - Jan 2, 2026
Total with taxes and fees
Wylder Tilghman Island
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
$129 nightly
The price is $147
Dec 14 - Dec 15
Total with taxes and fees
Crowne Plaza Annapolis by IHG
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (932)
"It was very comfortable and clean"
United States
Maria
$87 nightly
The price is $97
Jan 3 - Jan 4, 2026
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
Hypo-allergenic bedding, down comforters, in-room safe, desk
Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very Good, (1000)
"Clean room, fast and easy check in, made to order breakfast options. "
United States
Michael
$74 nightly
The price is $85
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hilton Garden Inn Annapolis
Terrace/patio
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
$164 nightly
The price is $187
Dec 21 - Dec 22
Total with taxes and fees
Historic Inns of Annapolis
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
$149 nightly
The price is $170
Dec 28 - Dec 29
Total with taxes and fees
Anchored Inn at Hidden Harbour Marina
Dinner served, American cuisine
Comfort Inn Conference Center

Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1001)
"It had good parking and restaurant in the hotel with good prices."
United States
Patrick
$99 nightly
The price is $112
Dec 15 - Dec 16
Total with taxes and fees
Comfort Inn Conference Center
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 Shady Side Hotel Reviews

DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

10/10 Excellent
"The staff was nice and the room was clean. My only complaint was that the remote in our room did not work well."
Ashlie 1-night trip
Posted 1 day ago
DoubleTree by Hilton Hotel Largo/Washington DC

Frequently asked questions

Searching for hotels with bars in Shady Side?
Though you might not find a hotel in Shady Side well-known for its bar, you will find 13 properties to choose from, some of which will have an onsite bar where you can unwind with an evening cocktail after sightseeing. While you're here, you can check out Shadyside Park and Northern Chesapeake Bay.
What are the best hotels with bars in Shady Side?
Here are some top hotels with bars in and around Shady Side: DoubleTree by Hilton Hotel Largo/Washington DC: Hotel with restaurant. Enjoy the bar, free parking, and breakfast. Crowne Plaza Annapolis by IHG: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. DoubleTree by Hilton Hotel Annapolis: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Historic Inns of Annapolis: Enjoy the bar, free WiFi, and room service. Comfort Inn Largo-Washington DC East: Hotel with restaurant. Enjoy the bar, free WiFi, and breakfast.
What is there to do in Shady Side?
In the area, you can visit Shadyside Park, London Town, and Maryland Quiet Waters Park, then find a cozy spot for a nightcap. Other places to see include Northern Chesapeake Bay and Chesapeake Bay.
When is the best time to visit Shady Side?
Visiting local bars in Shady Side is more fun when you know what the weather holds. These rainfall averages and temperatures can help you choose 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 Shady Side is 51 inches.
How can I get to Shady Side and around the area?
Here are some of your transportation options in and around Shady Side: Fly into Fort Meade, MD (FME-Tipton), which is located 21.6 mi (34.8 km) away from the city center. You can also search for flights into College Park, MD (CGS), which is 24.1 mi (38.7 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.

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