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Steps to Chesapeake Bay! 'Callaway Drive Retreat'

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

Living area
Exterior
Exterior
Living area
Living area

Reviews

9.4 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 6

Popular amenities

  • Kitchen
  • Washing machine
  • Deck or patio
  • Internet
  • Balcony or patio
  • Refrigerator

Explore the area

View 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

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

About this property

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

Add dates for prices

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House Rules

Check in after 4:00 PM
Minimum age to rent: 18
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 20224510
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that 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 and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

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 Alumni Hall. Discover the area's water adventures with nearby power boating, or enjoy the great outdoors with hiking.
View more Holiday homes in Shady SideOpens in a new window
Map
Shady Side, MD

What's nearby

  • Franklin Point State Park - 2 min walk - 0.2 km
  • U.S. Naval Academy - 38 min drive - 41.1 km
  • Northwest Stadium - 46 min drive - 54.4 km
  • MGM National Harbor Casino - 53 min drive - 61.7 km
  • Arundel Mills Mall - 60 min drive - 72.0 km

Getting around

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

Restaurants

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

Frequently asked questions

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

No, pets are not allowed at this property.

How much does it cost to stay at Steps to Chesapeake Bay, Callaway?

As of 13 July 2026, prices found for a 1-night stay for 2 adults at Steps to Chesapeake Bay, Callaway on 15 July 2026 start from NZ$573, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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

9.4

Exceptional

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. 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

9.2/10

Check-in

9.4/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

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

10/10 Excellent

Jeffrey H.

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

Military Bowl

Wonderful place
Stayed 2 nights in Dec 2024
Verified

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

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
From a partner site

10/10 Excellent

Jennifer

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

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

10/10 Excellent

Shawn T.

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

6/10 Okay

Tom P.

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

About the host

Hosted by Evolve

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