Search Guest Houses in Shady Side

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

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

Island Life! Kent Island Waterfront with Pool-Bring your boat!

10.0 out of 10, Exceptional, (184)
"Great location, clean and everything was just like it posted. Would 100% stay here again"
Island Life! Kent Island Waterfront with Pool-Bring your boat!

Riverview Retreat on Warehouse Creek

10.0 out of 10, Exceptional, (21)
"The property was beautiful and conveniently located between Baltimore and DC, not far from Annapolis. The owners were VERY helpful. It was very easy to access the property. (Sometimes we've had trouble finding the entrance or getting locks to work - no problems here what so ever) We had use of kayaks and paddle boards for the river, which was great for my teenage son. The owners gave great recommendations for local restaurants. The property is in a walkout basement which you access via a path....
The price is AED 889
AED 1,792 total
includes taxes & fees
2 May - 3 May
Riverview Retreat on Warehouse Creek

West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis

10.0 out of 10, Exceptional, (15)
"Very convenient! We really enjoyed our stay and the hosts were very accommodating! "
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis

Calico Cottage Guest House

10.0 out of 10, Exceptional, (8)
"This tiny house is tastefully furnished and, coupled with the quiet neighborhood, provides a relaxing, peaceful environment."
Calico Cottage Guest House
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.
Don't see what you're looking for?
See all available properties in Shady Side
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Shady Side

The Cottage

10.0 out of 10, Exceptional, (4)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The Cottage

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (212)
"The house was absolutely perfect for our USNA Reunion. About 10 steps to Gate 1 and just a few more to the heart of downtown made it a weekend we will remember. The host was responsive and accommodated our requests and was very kind. I would definitely stay here again."
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

9.8 out of 10, Exceptional, (76)
"We stayed at the host property for a long weekend in town for a family baby shower nearby. We were totally impressed with the cleanliness of the location, spacious accommodations and responsiveness of the host. There is a weekend farmers market and we wound up getting fresh produce to cook and some great food and desserts to eat. Parking was a breeze and the nearby park was wonderful for our daily walks. Highly recommended! 10 out of 10!!"
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
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.