Shady Side, MD

Travel Guide

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,859 reviews)
"So the entire experience was amazing. There was so much in walking distance. It was kind of weird because there were actually 3 inns and we didn't know which one we were in"

Reviewed on 28 September 2025

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Historic Inns of Annapolis
DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

4 out of 5
9100 Basil Court, Upper Marlboro, MD
The price is AED 356 per night from Nov 3 to Nov 4
AED 356
AED 402 total
3 Nov - 4 Nov
includes taxes & fees
Stay at this 4-star business-friendly hotel in Upper Marlboro. Enjoy free parking, breakfast (surcharge), and a 24-hour fitness center. Popular attractions Northwest ...
7.8/10 Good! (1,022 reviews)
"Nice"

Reviewed on 25 September 2025

DoubleTree by Hilton Hotel Largo/Washington DC
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

3 out of 5
55 Hampton Park Blvd, Capitol Heights, MD
The price is AED 309 per night from Oct 6 to Oct 7
AED 309
AED 353 total
6 Oct - 7 Oct
includes taxes & fees
Stay at this 3-star business-friendly hotel in Capitol Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
5.8/10 (1,896 reviews)
Great place for a stay near DCA
"Great place to stay and very helpful and approachable staff. The only downside was that the exercise room was undergoing remodeling and there was a very limited number of exercise machines."

Reviewed on 23 September 2025

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
See all 1,222 properties in Shady Side
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.
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Shady Side
Stay at this vacation home in Shady Side. Enjoy laundry facilities and air conditioning. Popular attractions Shadyside Park and Franklin Point State Park are ...
10/10 Exceptional! (2 reviews)
"The property is newly renovated and very comfortable. Property owner is responsive to any questions, and we enjoyed our stay here. Would recommend it for anyone staying in Shady Side."

Reviewed on 18 August 2025

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Saint Michaels
Stay at this cottage in St. Michaels. Enjoy a garden, laundry facilities, and tennis courts. Popular attractions Muskrat Park and Higgins Yacht Yard and Marina ...
9.4/10 Exceptional! (117 reviews)
"Beautifully restored historic home, in a quaint neighborhood, near the water and downtown. We loved it!"

Reviewed on 21 September 2025

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Annapolis
Stay at this vacation home in Annapolis. Enjoy free WiFi, a water park, and laundry facilities. Popular attractions John Smith House and Tose Family Tennis Center ...
10/10 Exceptional! (215 reviews)
"The home was absolutely perfect and the location was even more perfect. We loved everything about this property from the comfy beds to the amazing outdoor patio. We could not have asked for a better place to stay for our nephew's wedding at the academy!"

Reviewed on 1 October 2025

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
See all properties in Shady Side
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.

Popular places to visit

Shadyside Park

Explore the great outdoors at Shadyside Park, a lovely green space in Shady Side. Stroll along the area's waterfront, or simply savor its top-notch restaurants.

Shadyside Park

Captain Avery Museum

You can spend time exploring the galleries in Captain Avery Museum in Shady Side. Stroll along the area's waterfront, or simply savor its top-notch restaurants.

Captain Avery Museum