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Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Shady Side vacation home with kitchen

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Photo gallery for Steps to Chesapeake Bay! 'Callaway Drive Retreat'

A living room with two patterned sofas, a glass coffee table, a ceiling fan, a flat-screen TV, and a bookshelf with decorative items.
A spacious room with hardwood flooring, a large window, a chair, a small table, and a bookshelf.
A covered outdoor seating area with a table and chairs, surrounded by a grassy yard and trees.
A bedroom with a bed, bedside tables, a nightstand, a chair, a small table, a ceiling fan, and a window with a blind.
A kitchen with wooden cabinets, a microwave, a sink, and a dishwasher.

Reviews

9.4 out of 10
Exceptional

Entire home

3 bedrooms2 bathrooms

Popular amenities

  • Kitchen
  • Washer
  • Outdoor Space

Explore the area

View in a map
Shady Side, MD
  • Place, Franklin Point State Park
    ‪2 min walk‬
  • Place, U.S. Naval Academy
    ‪38 min drive‬
  • Place, Northwest Stadium
    ‪46 min drive‬
  • 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 Franklin Point State Park. Also, Northern Chesapeake Bay is within half a mile (1 km) and Shadyside Park is within 3 miles (5 km).
View more Vacation Homes in Shady SideOpens in a new window

What's nearby

  • Franklin Point State Park - 2 min walk - 0.1 miles
  • U.S. Naval Academy - 38 min drive - 25.6 miles
  • Northwest Stadium - 46 min drive - 33.8 miles
  • Arundel Mills Mall - 60 min drive - 44.8 miles
  • University of Maryland, College Park - 61 min drive - 40.6 miles

Getting around

  • Fort Meade, MD (FME-Tipton) - 47 min drive

Restaurants

  • ‪Bayside Bull - ‬19 min drive
  • ‪Pirates Cove Restaurant - ‬15 min drive
  • ‪Skippers Pier Restaurant and Dock Bar - ‬14 min drive
  • ‪Jesse Jay’s - ‬8 min drive
  • ‪Wharf 38 - ‬13 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

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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.
    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 and 18.2 mi (30-min drive) from Brownies Beach. Don't forget your sunscreen!

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

9.4

Exceptional

Rating 10 - Excellent. 6 out of 8 reviews
Rating 8 - Good. 1 out of 8 reviews
Rating 6 - Okay. 1 out of 8 reviews
Rating 4 - Poor. 0 out of 8 reviews
Rating 2 - Terrible. 0 out of 8 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Jeff H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful place to stay. The water is an added bonus!
Stayed 2 nights in Dec 2025
Verified review

10/10 Excellent

Jeffrey H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Military Bowl

Wonderful place
Stayed 2 nights in Dec 2024
Verified review

10/10 Excellent

Regina E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 2 nights in Jul 2024
Verified review

8/10 Good

Lucy C.

Liked: Cleanliness, location, listing accuracy

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.
Stayed 2 nights in Aug 2024
Verified review

10/10 Excellent

Deborah S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our host was so helpful making sure we understood the codes for the gate and the front door. The house was very clean. The kitchen was well equipped for cooking. Sadly it was too chilly to take advantage of the gazebo and grill.
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Shawn T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in Nov 2025
Verified review

6/10 Okay

Tom P.

Liked: Check-in, location, listing accuracy
Stayed 6 nights in Jun 2025

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