Steps to Chesapeake Bay! 'Callaway Drive Retreat'
Entire home in Shady Side, MD
Why you'll love this stay
Outdoor Living
Enjoy alfresco dining on a covered patio after bayside strolls.
Entertainment & Amenities
Stay connected with streaming, a full kitchen, and in-unit laundry.
Group & Family Friendly
Steps from the bay, perfect for family-friendly coastal escapes.
Property details
The space
STR00743
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
Guest access
Guests will have access to the entire property
Other things to note
- No smoking
- No pets allowed
- No events, parties, or large gatherings
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- There is free parking for 3 cars
- Quiet hours are from 10:00 PM to 8:00 AM
Registration details
000743
Sleeping arrangements
Bedroom 1
1 queen Bed
Bedroom 2
1 queen Bed
Bedroom 3
2 single Beds
What’s included
EV charger
Washer
Central heating
Kitchen
Wifi
Patio or balcony
TV
Hot water
Guest reviews
Todd
Great house for the price
August 2025
We needed a home relatively close to Herrington Harbor North to work on our boat. This house was a 15 minute drive which was perfect. The house is simple but adequate for what we needed. The mattresses are not comfortable and if replaced, we would stay there again.
Mila
Very clean home with lots of amenities!
July 2025
This was a lovely and very clean home. It also included several amenities such as bikes, a gazebo with picknick tables and aa mosquito mesh, and a grill. We had a great time exploring the area and walking to 'Sandy Beach', as well as visiting the nearby restaurants and farmers markets.
Christine
Cute place but not the best experience
November 2024
The owner kept it well supplied but we had issues with access, smells and some cleanliness. The owner should replace the temperamental electronic keypad. After driving 5.5 hrs, dealing with that was the last thing a renter wants to deal with. Should also leave a key for the front door in the key lock box. Not likely to rent again.
Lyndsay
Home away from home.
October 2024
Great place for a family. The neighborhood was beautiful (neighbors was nice). It was a ¹/² mile from the park. We took walks and rode bikes (that was provided 😊). The Calloway Drive Retreat should be renamed for Calloway Drive Escape! We felt like we got away from the world staying there. We will definitely be back again.
Know before you go
House rules
Check-in: 4:00pm
Checkout: 10:00am
No pets allowed
Min. age to rent: 18Minimum age to rent: 18
No smoking
No parties