10/10 Excellent
Jeff H.
Dec 28, 2025
Liked: Cleanliness
Jeff H.
Stayed 2 nights in Dec 2025
Entire home
Steps to Chesapeake Bay! 'Callaway Drive Retreat'
Shady Side vacation home with kitchen
Choose dates to view prices
Photo gallery for Steps to Chesapeake Bay! 'Callaway Drive Retreat'
Reviews
9.09.0 out of 10
Wonderful
Entire home
3 bedrooms2 bathrooms
Popular amenities
- Kitchen
- Washer
- Outdoor Space
Explore the area
Shady Side, MD
- Franklin Point State ParkPlace, Franklin Point State Park4 min drive
- Shadyside ParkPlace, Shadyside Park6 min drive
- Captain Avery MuseumPlace, Captain Avery Museum8 min drive
- Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)62 min drive
Room options
About the neighborhood
Shady Side
In Shady Side .Within a 5-minute walk of this Shady Side vacation home, you'll find Chesapeake Bay and Northern Chesapeake Bay. Franklin Point State Park and Shadyside Park are also within 3 miles (5 km).
What's nearby
- Franklin Point State Park - 4 min drive - 2.0 miles
- Shadyside Park - 6 min drive - 3.2 miles
- Captain Avery Museum - 8 min drive - 3.7 miles
- Galesville Heritage Museum - 14 min drive - 9.4 miles
- Smithsonian Environmental Research Center - 18 min drive - 12.3 miles
Getting around
- Fort Meade, MD (FME-Tipton) - 47 min drive
Restaurants
- Bayside Bull - 19 min drive
- Dunkin' - 19 min drive
- 7-Eleven - 10 min drive
- Jesse Jay’s - 8 min drive
- Happy Harbor Restaurant - 12 min drive
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
Steps to Chesapeake Bay! 'Callaway Drive Retreat'
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.
-- THE PROPERTY --
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
-- THE LOCATION --
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.
-- REST EASY WITH US --
Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.
-- POLICIES --
- 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
-- THE PROPERTY --
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
-- THE LOCATION --
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.
-- REST EASY WITH US --
Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.
-- POLICIES --
- 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
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Property amenities
Internet
- Available in the house: Internet access
Kitchen
- Coffee/tea maker
- Cookware, dishware, and utensils
- Dishwasher
- Microwave
- Refrigerator
- Stovetop
- Toaster
Dining
- Dining table
Bedrooms
- 3 bedrooms
- Bedsheets provided
Bathroom
- 2 bathrooms
- Towels provided
Living spaces
- Dining table
Entertainment
- Stereo
- TV with cable/satellite channels
Outdoor areas
- Patio
Laundry
- Washing machine
Comfort
- Heating
Pets
- No pets allowed
Suitability/Accessibility
- Smoking not allowed
Services and conveniences
- Iron/ironing board
Things to do
- Bicycles
- Hiking/biking trails nearby
- Motor boating nearby
Safety features
- Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
- Smoke detector (host has indicated there is a smoke detector on the property)
- Fire extinguisher
General
- Bicycles
Policies
Check-in
Check-in time starts at 4:00 PM
Minimum check-in age: 18
Check-out
Check-out before 10:00 AM
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Pets
- No pets allowed
Children and extra beds
- Children are welcome.
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
- This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, and a smoke detector in each accommodation.
Property is also known as
564527
Frequently asked questions
How close is Steps to Chesapeake Bay! 'Callaway Drive Retreat' to the airport?
This vacation home is 34.2 mi (47-min drive) away from the Fort Meade, MD (FME-Tipton) airport, the closest popular airport to the property.
Does Steps to Chesapeake Bay! 'Callaway Drive Retreat' have an airport shuttle?
Airport shuttle services are not available at this vacation home.
How close is Steps to Chesapeake Bay! 'Callaway Drive Retreat' to the beach?
This vacation home is 15.7 mi (34-min drive) from Triton Beach.
Does Steps to Chesapeake Bay! 'Callaway Drive Retreat' offer free breakfast?
This vacation home does not offer free breakfast.
Is there a casino at Steps to Chesapeake Bay! 'Callaway Drive Retreat'?
No, there is no casino at this vacation home.
What time is check-in at Steps to Chesapeake Bay! 'Callaway Drive Retreat'?
Check-in begins at 4:00 PM.
Is there free parking at Steps to Chesapeake Bay! 'Callaway Drive Retreat'?
Free parking is not available at this vacation home.
Does Steps to Chesapeake Bay! 'Callaway Drive Retreat' have a pool?
This vacation home does not have a pool.
Does Steps to Chesapeake Bay! 'Callaway Drive Retreat' have a spa?
There are no spa services available at this vacation home.
How close is Steps to Chesapeake Bay! 'Callaway Drive Retreat' to downtown Shady Side?
This vacation home is 1.9 mi away from Shady Side.
Steps to Chesapeake Bay! 'Callaway Drive Retreat' Reviews
Reviews
9.0
Wonderful
All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 4 out of 6 reviews
10 - Excellent
4
Rating 8 - Good. 1 out of 6 reviews
8 - Good
1
Rating 6 - Okay. 1 out of 6 reviews
6 - Okay
1
Rating 4 - Poor. 0 out of 6 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 6 reviews
2 - Terrible
0
10/10
Cleanliness
Reviews
10/10 Excellent
Shawn T.
Dec 21, 2025
Liked: Cleanliness
Shawn T.
Stayed 4 nights in Nov 2025
6/10 Okay
Tom P.
Jul 18, 2025
Tom P.
Stayed 6 nights in Jun 2025
10/10 Excellent
Jeffrey H.
Dec 29, 2024
Liked: Cleanliness
Military Bowl
Wonderful place
Jeffrey H.
Stayed 2 nights in Dec 2024
8/10 Good
Lucy C.
Aug 4, 2024
Liked: Cleanliness
Spacious in a cute neighborhood
We had lots of room to relax and hang out. The kitchen is very well appointed and we definitely could have cooked if we chose to. We enjoyed walking with nice views of the ocean. We especially enjoyed the osprey hanging out near their nest right off the pier.
Lucy C.
Stayed 2 nights in Aug 2024
10/10 Excellent
Regina E.
Jul 14, 2024
Liked: Cleanliness
Perfect Location
The place is cute and spacious enough for friend gathering. It is only 5mins away from the community beach and 25-30 from the bigger beaches. Perfect for a weekend getaway.
Regina E.
Stayed 2 nights in Jul 2024