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Compare 3 Guest Houses in Shady Side with updated reviews, rates, and availability.

Island Life! Kent Island Waterfront with Pool-Bring your boat!
Island Life! Kent Island Waterfront with Pool-Bring your boat!
10.0 out of 10, Exceptional, (184)

Riverview Retreat on Warehouse Creek
Riverview Retreat on Warehouse Creek
10.0 out of 10, Exceptional, (21)
The price is AED 889
AED 1,792 total
includes taxes & fees
2 May - 3 May

West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
10.0 out of 10, Exceptional, (15)

Calico Cottage Guest House
Calico Cottage Guest House
10.0 out of 10, Exceptional, (8)
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.
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Other property types in Shady Side

The Cottage
The Cottage
10.0 out of 10, Exceptional, (4)

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!
10.0 out of 10, Exceptional, (212)

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
9.8 out of 10, Exceptional, (76)
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.
Recent reviews of Shady Side hotels
Recent reviews of Shady Side hotels

Historic Inns of Annapolis
5/5 Excellent
From the moment we walked in the door…
"From the moment we walked in the door we were warmly greeted and felt welcome. Once key was in hand we made our way to our beautiful room that was clean ready for us.
The staff gave us excellent dinner recommendations, the walk to the restaurant we chose was lovely, so many fun shops and charming buildings, the location of Historic Inns of Annapolis is perfect.
I highly recommend the Historic Inns of Annapolis and I hope to visit again someday. "
A verified traveler stayed at Historic Inns of Annapolis
Posted 3 hours ago