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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

9.4 out of 10
Exceptional

Highlights

  • Cook, dine, and unwind
    Top-rated for its fully equipped kitchen, perfect for every meal.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
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 Tose Family Tennis Center. Discover the area's water adventures with nearby power boating, or enjoy the great outdoors with hiking/biking trails.
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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
  • Annapolis City Dock - 40 min drive - 42.2 km
  • Northwest Stadium - 46 min drive - 54.4 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
  • ‪South County Cafe - ‬12 min drive
  • ‪7-Eleven - ‬10 min drive
  • ‪Boat House - ‬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.

How much does it cost to stay at Steps to Chesapeake Bay! 'Callaway Drive Retreat'?

As of 28 Aug 2026, prices found for a 1-night stay for 2 adults at Steps to Chesapeake Bay! 'Callaway Drive Retreat' on 30 Aug 2026 start from AU$903, 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).

About the host

Hosted by Evolve

Host profile image

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