Shady Side Holiday Packages

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With Wotif's amazingly competitive prices, you'll be packing your suitcase and soaring through the skies in no time at all.

Shady Side Accommodation

Hoping to stay in the vicinity of Shady Side? You may want to consider Annapolis, as it's the nearest place that has any Wotif-listed properties. If you're into plush bedding and first-rate service, you'll love the Loews Annapolis Hotel (126 West St) and The Westin Annapolis (100 Westgate Cir). If you'd prefer book something more affordable, the Holiday Inn Express & Suites Annapolis (2451 Riva Rd) or the Motel 6 Annapolis (1542 Whitehall Rd) could be right up your alley.

Car Hire in Shady Side

Trying to decide which car hire outlet to pick is really very easy when arriving at Baltimore Washington International Thurgood Marshall Airport. With Hertz just a short walk away from the luggage claim area, you and your squad will be driving off before you know it.

Holidays to Shady Side

Eager to scratch your travel itch in Shady Side? We don't blame you. But before you fly off to this exciting destination, how about we fill you in on the essential details?

If you're arriving here via the city of Davidsonville, Shady Side is 16 kilometres to the southeast. If you're coming in from Annapolis, you'll need to head south for 16 kilometres.

If you've been trying to recall just how many people reside in this part of Western Shore of Maryland but your mind's in packing mode, don't stress — we can help. At the last count, the population was 6 000.

Top Shady Side hotels

Bay views with kayaks, bikes, fire pit, crabbing and more

Bay views with kayaks, bikes, fire pit, crabbing and more

Shady Side
Bay views with kayaks, bikes, fire pit, crabbing and more: Family-friendly holiday home with free WiFi and parking.
Nice Get Away
"Cute cottage in quiet neighborhood for a get away to the Eastern shore. Description is accurate and Mary was easy to communicate with. We enjoyed our stay."

Reviewed on 22 Jun. 2025

Bay views with kayaks, bikes, fire pit, crabbing and more
Calloway Drive Retreat | House in Shady Side

Calloway Drive Retreat | House in Shady Side

Shady Side
Calloway Drive Retreat | House in Shady Side: Holiday home with a water park and parking.
Military Bowl
"Wonderful place"

Reviewed on 29 Dec. 2024

Calloway Drive Retreat | House in Shady Side
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
Historic Inns of Annapolis: Pet-friendly hotel with free WiFi and a bar/lounge. Located in the historical district.
"The property was beautiful. The historic surroundings made the placement of the hotel perfect. Many attractions, including quality shops and the harbor were within walking distance. The staff were always available willing to help. I would stay here again."

Reviewed on 13 Aug. 2025

Historic Inns of Annapolis
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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.