Steps to Chesapeake Bay! 'Callaway Drive Retreat'

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 house with a white exterior, a porch, and a boat trailer in the yard.
A single-story house with a front porch, a well-maintained lawn, and a driveway leading to the front door.
A living room with a patterned sofa, a glass coffee table, a ceiling fan, and large windows with curtains.
A spacious living room with a ceiling fan, two patterned sofas, a coffee table, and a view into the kitchen.

Reviews

9.2 out of 10
Wonderful

Highlights

  • Discover nearby landmarks
    Near Chesapeake Bay

Popular amenities

  • Patio
  • Refrigerator
  • Internet
  • Washing machine
  • Non-smoking
  • Microwave

Explore the area

View map
Shady Side, MD
  • Place, Franklin Point State Park
    ‪2 min walk‬
  • Place, Northern Chesapeake Bay
    ‪3 min walk‬
  • Place, MGM National Harbor Casino
    ‪54 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪61 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Bedroom 3

2 Single Beds

2 bathrooms

Full Bathroom

Full Bathroom

Spaces

Deck or patio
Kitchen
Outdoor play area

Add dates for prices

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Property grounds
Private Cottage on gated estate
Arundel on the Bay
  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
9.8 out of 10, Exceptional, (42 reviews)
Private Cottage on gated estate

About the area

Shady Side

Shady Side is home to this holiday home. Thanksgiving Farm Wines and South River Golf Links are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Chesapeake Beach Water Park and Chesapeake Beach Railway Museum. Looking to enjoy an event or a game while in town? See what's happening at Navy-Marine Corps Memorial Stadium or Tose Family Tennis Center. Discover the area's water adventures with nearby power boating, or enjoy the great outdoors with hiking.
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Map
Shady Side, MD

What's nearby

  • Franklin Point State Park - 2 min walk - 0.2 km
  • Northern Chesapeake Bay - 3 min walk - 0.3 km
  • U.S. Naval Academy - 38 min drive - 41.1 km
  • Northwest Stadium - 46 min drive - 54.4 km
  • MGM National Harbor Casino - 54 min drive - 61.3 km

Getting around

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

Restaurants

  • ‪Bayside Bull - ‬19 min drive
  • ‪Boat House - ‬12 min drive
  • ‪7-Eleven - ‬10 min drive
  • ‪South County Cafe - ‬12 min drive
  • ‪Pirates Cove Restaurant - ‬15 min drive

Frequently asked questions

Is Steps to Chesapeake Bay! 'Callaway Drive Retreat' pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Steps to Chesapeake Bay! 'Callaway Drive Retreat'?

Check-in begins at 4:00 PM.

What time is check-out at Steps to Chesapeake Bay! 'Callaway Drive Retreat'?

Checkout is at 10:00 AM.

Where is Steps to Chesapeake Bay! 'Callaway Drive Retreat' located?

Situated in Shady Side, this holiday home is steps away from Franklin Point State Park and Chesapeake Bay. Northern Chesapeake Bay and Shadyside Park are also within 3 miles (5 km).

Reviews

9.2

Wonderful

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 7 out of 10 reviews
Rating 8 - Good. 2 out of 10 reviews
Rating 6 - Okay. 1 out of 10 reviews
Rating 4 - Poor. 0 out of 10 reviews
Rating 2 - Terrible. 0 out of 10 reviews

9.8/10

Cleanliness

9.4/10

Check-in

9.4/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The place is in a good quiet location. It has everything you need. Plenty of space and a great area on the back to hang out.
Stayed 3 nights in Sep 2026
Verified review

10/10 Excellent

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

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

Military Bowl

Wonderful place
Stayed 2 nights in Dec 2024
Verified review

10/10 Excellent

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

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
From a partner site

10/10 Excellent

Beautiful Cottage

We stayed here while my son went to summer camp at USNA and enjoyed the peaceful neighborhood. A couple hiccups occurred at the beginning of the trip but Charles was very open to resolving them with open and timely communication. The kids LOVED having the bikes to ride around the neighborhood and the beach is quiet with a lot of rocks for the kids to play on. The park area for the neighborhood has the most beautiful sunrises. We went into DC some to see the sites and it made for an easy drive to the metro station to get into the city. It was so nice to be able to come back to a peaceful cottage after a day in the city. The house is stocked with anything you would need in the kitchen to make for a comfortable stay. Would stay again if the opportunity arises!
Verified review

10/10 Excellent

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

8/10 Good

Liked: Cleanliness, check-in, communication, listing accuracy
Stayed 4 nights in Jul 2026
Verified review

10/10 Excellent

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

6/10 Okay

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