Shady Side, MD

Travel Guide

Aerial view of Annapolis capital city of Maryland state with expensive waterside properties along the Chesapeake Bay, state capital building and naval academy, dreamy blue sky
An aerial view of a beach with clear water, a sandy shore, and visible footprints.
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
$124 nightly
The price is $142 total per night from Jul 21 to Jul 22
$142 total
Jul 21 - Jul 22
Total with taxes and fees
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 ...
9/10 Wonderful! (1,857 reviews)
"Bed had a wear to it where I rolled . Tub was rusted with grout having mold . The product container was suppose to hang on the wall but kept falling off and breaking the bottles so they did not work. Def not worth the price we paid. It was in a great vicinity."

Reviewed on Jun 20, 2026

Historic Inns of Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $127 total per night from Jun 21 to Jun 22
$127 total
Jun 21 - Jun 22
Total with taxes and fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
DoubleTree by Hilton Hotel Annapolis
Comfort Inn Largo-Washington DC East

Comfort Inn Largo-Washington DC East

3 out of 5
9421 Largo Drive West Upper Marlboro MD
$84 nightly
The price is $95 total per night from Jul 14 to Jul 15
$95 total
Jul 14 - Jul 15
Total with taxes and fees
Book a stay at this business-friendly hotel in Upper Marlboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
8/10 Very Good! (652 reviews)
"The staff cleaning was terrible , they open my door and I still inside … no knock door !!!"

Reviewed on Jun 20, 2026

Comfort Inn Largo-Washington DC East
See all 1,197 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.
Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Shady Side MD
Book a stay at this family-friendly vacation home in Shady Side. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Shadyside Park and Captain ...
Lovely bay views with kayaks, bikes, fire pit, crabbing & more
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 MD
Stay at this vacation home in Annapolis. Enjoy free WiFi, laundry facilities, and patios. Popular attractions John Smith House and Tose Family Tennis Center ...
10/10 Exceptional! (247 reviews)
"John is an excellent and generous host. Definitely recommend if you are planning to visit Annapolis!"

Reviewed on Jun 15, 2026

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Firefly Cottage at the Cape, Hot Tub, Community beach, summer fun, USNA visits.

Firefly Cottage at the Cape, Hot Tub, Community beach, summer fun, USNA visits.

Annapolis MD
Stay at this cottage in Annapolis. Enjoy free breakfast, free WiFi, and a garden. Popular attractions Annapolis City Dock and Sandy Point State Park are located ...
10/10 Exceptional! (110 reviews)
"We had a wonderful three-night stay and couldn’t have been more pleased with both the property and the host. The cottage was exceptionally comfortable, relaxing, spotless, and very dog-friendly. It provided the perfect place to unwind while visiting family.We did experience a power outage during ..."

Reviewed on Jun 14, 2026

Firefly Cottage at the Cape, Hot Tub, Community beach, summer fun, USNA visits.
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

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