USA Maryland Shady Side Listing #107414

Calloway Drive Retreat - Shady Side, MD

Take 3D Home Tour
7 reviews
Max. occupancy: 6 2 queen beds, 1 twin lower bunk bed, 1 twin upper bunk bed 3 bedrooms 2 bathrooms No pets 
Address provided after booking

Worry-free booking

Enjoy peace of mind with simple cancellation and optional travel insurance. Learn more >

Expert cleaning

Pro housekeepers clean thoroughly and provide fresh linens before every stay.

Local support

Count on 24/7 guest care and local teams everywhere we operate.


Smart locks or lockboxes at many homes offer smooth, contactless check-in.

Calloway Drive Retreat | House in Shady Side

Steps from the bay, curate all of your favorite vacation memories at the Calloway Drive Retreat! Spacious, tastefully decorated, and ready to host - this lovely home boasts comfortable furnishings and modern amenities. Hang out inside amongst the cool air of the partial air-conditioning while cooking, streaming your favorite shows, and refreshing your vacation garb in the private washer/dryer.

Outside, enjoy dining alfresco on the covered patio, visiting with your loved ones under the radiant sunshine, or taking the provided bikes for a ride through the neighborhood. Less than 20 miles from your stay, discover the Franklin Point Park Beach, Captain Avery Museum, Beverly Triton Nature Park, Renditions Golf Course, Chesapeake Beach Water Park, and Historic Annapolis.

House Rules

This Vacasa Guestworks vacation rental is operated and managed locally by an independent host.
Prior to your arrival, you will receive local host contact information, who will manage your guest reservation. Your local host will provide in-stay support, secure entry, and arrange pre- and post-stay housekeeping services.
If you need anything during your stay, the home’s independent local host is ready to help 24/7! Guestworks is a service offering of Vacasa that allows homeowners to smoothly and efficiently manage their own properties.

County permit number: STR00743

You must be 21 years or older to rent this property.




Washer/dryer : Private

Heating & cooling

Central AC

Partial AC

Space heater

Kitchen & dining






Beach access





Wireless router

HBO streaming

Netflix streaming


Nearby activities & attractions


On-site activities

Adult bikes



Beach chairs

Parking & access

Electric vehicle charger

Safety & accessibility

Accessible bath/shower

Map showing the location of the Unit

7 reviews