[See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Calloway Drive Retreat | House in Shady Side Vacation home in Shady Side with kitchen and patio ![Outdoor dining](https://images.trvl-media.com/lodging/97000000/96500000/96499400/96499333/0909d960.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96500000/96499400/96499333/905a9be1.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior](https://images.trvl-media.com/lodging/97000000/96500000/96499400/96499333/939ca0ce.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96500000/96499400/96499333/6d0565ad.jpg?impolicy=resizecrop&rw=297&ra=fit) ![TV, books, stereo](https://images.trvl-media.com/lodging/97000000/96500000/96499400/96499333/7d3d2fb6.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Amenities - Policies - Location Escape to Calloway Drive Retreat, a lovely home near the bay where you can create lasting memories. Relax in the cool air of partial air-conditioning while streaming your favorite shows or take advantage of modern amenities like a private washer/dryer and bikes for neighborhood rides. 9.0 Wonderful ### Entire home 3 bedrooms2 bathroomsSleeps 6 ## Popular amenities - Kitchen - Washer - Dryer - Outdoor space - Parking available - Air conditioning ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire home to yourself and will only share it with other guests in your party. ### Calloway Drive Retreat | House in Shady Side Calloway Drive Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' 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. 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. 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. House Rules There is free parking for 3 car(s). Check in time: 4:00 PM Check out time: 10:00 AM All guests shall abide by Vacasa’s good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10 p.m. to 8 a.m. No smoking is permitted anywhere on the premises. This Vacasa Guestworks vacation rental is operated and managed locally by an independent host. Prior to your arrival, you will receive local host contact information, who will manage your guest reservation. Your local host will provide in-stay support, secure entry, and arrange pre- and post-stay housekeeping services. If you need anything during your stay, the home’s independent local host is ready to help 24/7! Guestworks is a service offering of Vacasa that allows homeowners to smoothly and efficiently manage their own properties. Parking notes: There is free parking available for 3 vehicles. Damage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit. More information can be downloaded from the "Rental Agreement" on the checkout page. Due to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation. ## Property amenities ### Beach - Beach nearby ### Internet - Available in the house: Internet access ### Parking and transportation - Electric car charging station on site - Parking on site ### Kitchen - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Microwave - Oven - Refrigerator - Stovetop ### Bedrooms - 3 bedrooms - Bedsheets provided ### Bathroom - 2 bathrooms - Towels provided ### Entertainment - Books - Stereo - TV with cable/satellite channels ### Outdoor areas - Patio ### Laundry - Laundry facilities - Washing machine ### Comfort - Air conditioning - Heating ### Pets - No pets allowed ### Suitability/Accessibility - Smoking not allowed - Note from host: Smoking is not permitted anywhere on the premises. ### Services and conveniences - Iron/ironing board ### Things to do - Bicycles - Water park - Birdwatching nearby - Fishing nearby - Hiking/biking trails nearby - Motor boating nearby - Swimming nearby - Wildlife walks 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 - Electric car charging station ## Similar properties ![Exterior](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/5eca3b46_edited_e784.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side Shady Side - Air conditioning - Laundry - Parking available - Microwave 10 Exceptional 3 reviews CA $202 CA $598 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-31&endDate=2025-11-01&selected=116005601&PinnedHotelID=116005601&HadPinnedHotel=true®ionId=-1&adults=2) ![Marina](https://images.trvl-media.com/lodging/106000000/105760000/105758700/105758639/9f651e90.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Floating 2 bed 2 bath condo stunning views of the bay Stevensville - Kitchen - Pet-friendly - Parking available - Barbecue grill 7.0 Good 6 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-05&endDate=2025-11-06&selected=105758639&PinnedHotelID=105758639&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor dining](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/60e252be.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Waterfront Getaway, Dock Your Boat & Play! 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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 ### Property is also known as 107414 ## About the area ![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 - Shadyside Park - 8 min drive - 4.5 km - Navy-Marine Corps Memorial Stadium - 39 min drive - 41.1 km - Annapolis City Dock - 41 min drive - 42.5 km - U.S. Naval Academy - 42 min drive - 42.9 km - Maryland Quiet Waters Park - 53 min drive - 44.2 km #### Getting around - Fort Meade, MD (FME-Tipton) - 47 min drive #### Restaurants - ‪Dunkin' - ‬19 min drive - ‪Pirates Cove Restaurant - ‬15 min drive - ‪Boat House - ‬12 min drive - ‪Skippers Pier Restaurant and Dock Bar - ‬14 min drive - ‪Happy Harbor Restaurant - ‬12 min drive ## Frequently asked questions ### Is Calloway Drive Retreat | House in Shady Side pet-friendly? > No, pets are not allowed at this property. ### What time is check-in at Calloway Drive Retreat | House in Shady Side? > Check-in begins at 4:00 PM. ### What time is check-out at Calloway Drive Retreat | House in Shady Side? > Check-out is at 10:00 AM. ### Where is Calloway Drive Retreat | House in Shady Side located? > Situated near the beach, this vacation home is within a 5-minute walk of Chesapeake Bay and Northern Chesapeake Bay. Franklin Point State Park and Shadyside Park are also within 3 mi (5 km). ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Calloway Drive Retreat | House in Shady Side Reviews 9.0 ### Wonderful All reviews shown are from real guest experiences. Only travellers 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.ca/lp/b/content-guidelines) ### 10 Cleanliness ### 10 Location 10 - Excellent 5 8 - Good 2 6 - Okay 1 4 - Poor 0 2 - Terrible 0 ### 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 ### 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 This review comes from a trusted partner site and has not been verified. ### 10/10 Excellent #### Doug M. Apr 23, 2024 #### The great quiet It is just the perfect space to spend quality time with your family. The beach is in walking distance! So awesome!! ##### Doug M. Stayed 3 nights in Apr 2024 This review comes from a trusted partner site and has not been verified. ### 8/10 Good #### karen w. Sep 1, 2024 #### Great place for a getaway Closeness to my sons house. Room for those who participated. Wish we could stay longer. Life just speeds by ##### karen w. Stayed 3 nights in Aug 2024 ### 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 This review comes from a trusted partner site and has not been verified. ### 10/10 Excellent #### Rachel P. Oct 12, 2023 #### Charming cottage in a beachy community Loved the location of this cottage and the amenities that the rental and the neighborhood afford. We loved riding bikes around the neighborhood, to the beach and pier, and generally enjoying the proximity to the Bay. The home is well appointed with laundry, a fully equipped kitchen, and fast internet. Highly recommend this place, especially for families. ##### Rachel P. ### 6/10 Okay #### Tom P. Jul 18, 2025 Liked: Check-in, location, listing accuracy ##### Tom P. 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