Search Guest Houses in Shady Side

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

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, (183)
"Our host Jon was so nice, checked in with us to make sure all was good, and it was. He had the place decorated for Christmas and even had a tree - we appreciated it very much since we were not home for Christmas. Beautiful setting on Cox creek. The guest house was well maintained and fully equipped kitchen. Very Comfortable beds and bedding which we find unique for VRBOs. "
Island Life! Kent Island Waterfront with Pool-Bring your boat!

Riverview Retreat on Warehouse Creek

10.0 out of 10, Exceptional, (18)
"My kids and I fell in love with Riverview Retreat. I wanted a place to spend Thanksgiving with my daughter as she's in Baltimore for the next two years (we're in TX). I wanted something out of the city and Anapolis rentals were sold out. I expanded my search, found Riverview Retreat, and am so glad I did. RR is perhaps the most comfortable, beautiful rental on record for us (and we rent a lot). PLENTY of room for the four of us (and) our doodle. Large sectional we all piled on for movies, large...
The price is SAR 585
SAR 1,440 total
includes taxes & fees
13 Mar - 14 Mar
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, (3)
"Couldn’t have asked for better- I appreciate the communication and willingness to work with us on a quick turn around trip. Clean. Easy to get to. Accurate description. Quiet neighborhood. 10/10 would stay again. "
The price is SAR 863
SAR 1,608 total
includes taxes & fees
20 Mar - 21 Mar
The Cottage

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

9.6 out of 10, Exceptional, (17)
"Very clean, everything as described. Awesome host, communication an A+. Would definitely stay again, if we are in the area."
Bay views with kayaks, bikes, fire pit, crabbing and more

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

10.0 out of 10, Exceptional, (208)
"John was a FABULOUS host! Communication was easy and the property is PERFECT! Walking distance to everything you would need and LOVED being directly across from the Naval Academy! THANK YOU John! Cheers!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
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.