Title: Steps to Chesapeake Bay! 'Callaway Drive Retreat' Reviews, Deals & Photos 2026 - Expedia [See all properties](http://www.expedia.com/Hotel-Search?regionId=6264943&destination=Shady+Side%2C+Maryland%2C+United+States+of+America&selected=123375338&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Steps to Chesapeake Bay! 'Callaway Drive Retreat' ## Photo gallery for Steps to Chesapeake Bay! 'Callaway Drive Retreat' ![TV, stereo - Steps to Chesapeake Bay! 'Callaway Drive Retreat' (Shady Side)](https://images.trvl-media.com/lodging/124000000/123380000/123375400/123375338/67d0a491.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Outdoor dining - Steps to Chesapeake Bay! 'Callaway Drive Retreat' (Shady Side)](https://images.trvl-media.com/lodging/124000000/123380000/123375400/123375338/70a8b861.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior - Steps to Chesapeake Bay! 'Callaway Drive Retreat' (Shady Side)](https://images.trvl-media.com/lodging/124000000/123380000/123375400/123375338/599de4fd.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, stovetop, dishwasher - Steps to Chesapeake Bay! 'Callaway Drive Retreat' (Shady Side)](https://images.trvl-media.com/lodging/124000000/123380000/123375400/123375338/2e90e704.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior - Steps to Chesapeake Bay! 'Callaway Drive Retreat' (Shady Side)](https://images.trvl-media.com/lodging/124000000/123380000/123375400/123375338/a69caba8.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies Steps to Chesapeake Bay! 'Callaway Drive Retreat' provides a playground and more. ## Reviews 9.0 Wonderful ### Entire home 3 bedrooms2 bathrooms ## Popular amenities - Kitchen - Washer - Outdoor Space ## Add dates for prices Check-in Check-out Travelers ## 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 ## 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 ## Similar properties ![Sports facility](https://images.trvl-media.com/lodging/54000000/53610000/53607200/53607104/w3837h2557x3y3-2a631d3e.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Hyatt Place National Harbor Oxon Hill - Pet friendly - Free WiFi - Restaurant - Air conditioning 9.4 Exceptional 2,086 reviews $152 nightly $180 total Apr 26 - Apr 27 Total with taxes and fees [](https://www.expedia.com/Hotel-Search?startDate=2026-04-26&endDate=2026-04-27&selected=53607104&PinnedHotelID=53607104&HadPinnedHotel=true®ionId=-1&adults=2) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4400/4305/w3836h2558x4y3-b10a8dce.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Hilton Arlington Rosslyn The Key Rosslyn - 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You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation ## About the neighborhood Shady Side is home to this vacation 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 motor boating nearby, or enjoy the great outdoors with hiking/biking trails. [Visit our Shady Side travel guide](https://www.expedia.com/Shady-Side.dx6264943) [View more Vacation Homes in Shady Side](https://www.expedia.com/Shady-Side-Private-Vacation-Homes.d6264943-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C38.81613%2C-76.50105&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=sb96ptGOOzaKxLUBXvvKYzv5EyY=) Shady Side, MD ### 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 ## Frequently asked questions ### Is Steps to Chesapeake Bay! 'Callaway Drive Retreat' pet-friendly? ### What time is check-in at Steps to Chesapeake Bay! 'Callaway Drive Retreat'? ### What time is check-out at Steps to Chesapeake Bay! 'Callaway Drive Retreat'? ### Where is Steps to Chesapeake Bay! 'Callaway Drive Retreat' located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Steps to Chesapeake Bay! 'Callaway Drive Retreat' Reviews ## Reviews ### 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. [More information](https://www.expedia.com/lp/b/content-guidelines) 10 - Excellent 4 8 - Good 1 6 - Okay 1 4 - Poor 0 2 - Terrible 0 ### 10 Cleanliness ### 10 Location ## Reviews Verified ### 10/10 Excellent #### Regina E. Jul 14, 2024 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. ##### Regina E. Stayed 2 nights in Jul 2024 Verified ### 8/10 Good #### Lucy C. Aug 4, 2024 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. ##### Lucy C. Stayed 2 nights in Aug 2024 Verified ### 10/10 Excellent #### Jeff H. Dec 28, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy Wonderful place to stay. The water is an added bonus! ##### Jeff H. Stayed 2 nights in Dec 2025 Verified ### 10/10 Excellent #### Jeffrey H. Dec 29, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Military Bowl Wonderful place ##### Jeffrey H. Stayed 2 nights in Dec 2024 Verified ### 10/10 Excellent #### Shawn T. Dec 21, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy ##### Shawn T. Stayed 4 nights in Nov 2025 Verified ### 6/10 Okay #### Tom P. Jul 18, 2025 Liked: Check-in, location, listing accuracy ##### Tom P. Stayed 6 nights in Jun 2025