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
$130 nightly
The price is $148 total per night from Jul 1 to Jul 2
$148 total
Jul 1 - Jul 2
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! (1,856 reviews)
"Maryland Inn is an absolutely fantastic location, but that’s about the only positive I have for it. There’s quite a stench to the place from the time you walk in the front door. We had room 1301. It looks very nice in pictures, but it has the same odor as in the hallways, and the floor was insane ..."

Reviewed on Jun 19, 2026

Historic Inns of Annapolis
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
$100 nightly
The price is $113 total per night from Jun 24 to Jun 25
$113 total
Jun 24 - Jun 25
Total with taxes and fees
Book a stay at this business-friendly hotel in Capitol Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
6/10 (2,030 reviews)
"Staff was extremely helpful"

Reviewed on Jun 20, 2026

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
$111 nightly
The price is $127 total per night from Jul 5 to Jul 6
$127 total
Jul 5 - Jul 6
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
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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