Shady Side Holiday Packages

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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

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
The price is AU$297 per night from 19 Apr to 20 Apr
AU$297
19 Apr - 20 Apr
includes taxes & fees
Graduate by Hilton Annapolis: Pet-friendly hotel with free WiFi and a bar/lounge. Located in the historical district.
The room was clean and comfortable. The hotel was decorated with a fun nautical theme. The location is excellent and close to dining and shopping.

Reviewed on 31 Mar 2026

Opens in a new windowGraduate by Hilton Annapolis
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
The price is AU$265 per night from 19 Apr to 20 Apr
AU$265
19 Apr - 20 Apr
includes taxes & fees
Historic Inns of Annapolis: Pet-friendly hotel with free WiFi and a bar/lounge. Located in the historical district.
The parking valet was wonderful- so easy to park and also gave us recommendations of where to eat! Front desk personnel were also lovely.

Reviewed on 1 Apr 2026

Opens in a new windowHistoric 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
Fully refundableReserve now, pay when you stay
The price is AU$187 per night from 14 Apr to 15 Apr
AU$187
14 Apr - 15 Apr
includes taxes & fees
DoubleTree by Hilton Hotel Largo/Washington DC: Pet-friendly hotel with free parking and an indoor pool. Located near a metro station.
The management team was horrible. My grandson and i played in the pool ( which was dirty ) with a nerf football alll afternoon with no problems. We attempted to go back around 6pm with the same nerf football and we were told that it wasnt allowed....there was no signs specifically addressing this ...

Reviewed on 31 Mar 2026

Opens in a new windowDoubleTree by Hilton Hotel Largo/Washington DC
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