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
The price is $148 total per night from Jul 1 to Jul 2
$148 total
per night
Jul 1 - Jul 2
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! (1,865 reviews)
"At first we were placed in the Calvert House but then switched to the Johnson. The shower plumbing was broken. The shower soap pump did not work. The tub porcelain was chipped and the pillows were very hard. The door did not seal at the bottom and hall light came in. Air conditioning was noisy. I ..."

Reviewed on Jun 22, 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
The price is $127 total per night from Jul 2 to Jul 3
$127 total
per night
Jul 2 - Jul 3
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
The price is $95 total per night from Jul 14 to Jul 15
$95 total
per night
Jul 14 - Jul 15
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! (656 reviews)
"Room smelled like smoke and weed. Mold present around the window. No pull down blind to block. The exterior lights. Just a see through sheer blind."

Reviewed on Jun 22, 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
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.
Grace Cottage, St Michaels Walk to everything!

Grace Cottage, St Michaels Walk to everything!

Saint Michaels MD
Stay at this vacation home in St. Michaels. Enjoy laundry facilities, in-room fireplaces, and air conditioning. Popular attractions Saint Marys Square and Saint ...
10/10 Exceptional! (6 reviews)
"We had such a wonderful time staying at Grace Cottage. Lisa, the hostes, was very responsive and very, very kind. The cottage was right in the middle of all shopping and restaurants. It is beautifully decorated and is totally stocked with everything you would need. Thank you so much Lisa for making ..."

Reviewed on May 8, 2026

Grace Cottage, St Michaels Walk to everything!
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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