Shady Side house rentals
We found 478 house rentals — enter your dates for availability
Explore Shady Side house rentals
Lovely bay views with kayaks, bikes, fire pit, crabbing & more
Sleeps 8 · 3 bedrooms · 2 bathrooms
Spacious 6-bedroom country house on the water in beautiful Shady Side with WiFi
Sleeps 13 · 6 bedrooms · 3+ bathrooms
Waterfront Sanctuary only 50 Min. From DC/Balt.
Sleeps 12 · 5 bedrooms · 4 bathrooms
West River Waterfront Escape with Boat Lift, Kayaks & Bay Views
Sleeps 8 · 4 bedrooms · 3 bathrooms
Steps to Chesapeake Bay! 'Callaway Drive Retreat'
Sleeps 6 · 3 bedrooms · 2 bathrooms
Zen Sunset Retreat on Waterfront at West River, MD
Sleeps 10 · 5 bedrooms · 4+ bathrooms
Top rated house rentals - Shady Side
Fantastic house - clean, warm & perfectly located to get around Annapolis
Property was fully equipped with everything we needed - like a ‘home away from home’. John was extremely helpful and informative during our planning and everything was as we expected. Thanks a lot!
Simon M.
Stayed Dec 2017
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More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
Are there any holiday home rentals in Shady Side?
Check out our 478 holiday home rentals and begin planning your trip to Shady Side. Whether you want to stay in Beverly Beach, Cape Anne, Deale Beach or another popular neighbourhood, you'll find the ideal house on Stayz.
How much does it cost to stay in a holiday rental house in Shady Side?
Where you stay, when you decide to travel and the length of your trip will influence the price of a holiday home rental in Shady Side. Enter your travel details on Stayz to easily compare options and then pick the right one for you.
When is the best time to rent a holiday house in Shady Side?
If you're thinking about visiting Shady Side during your trip to Southern Maryland, consider July. Many guests book a Stayz holiday home rental at this time of year when daily temperatures are between 22ºC and 30ºC.
Where can I rent a Shady Side holiday house with great views?
Use our convenient "Location" filter to find a holiday home rental with the views you dream of waking up to. Start by entering the dates you want to book your house in Shady Side, then narrow your search based on the sort of area you'd prefer to stay in.
Does Shady Side have any weekend house rentals?
Browse our weekend rentals and prepare for an unforgettable few days away. Our main tips for booking the perfect house in Shady Side? Be flexible when searching and modify your travel dates until you find the holiday home rental that fits your style.
Are there any pet-friendly house rentals in Shady Side?
With our convenient filter tool, finding a pet-friendly holiday home rental in Shady Side is a walk in the park. Simply click on "Pets allowed" to view houses that feature extras to make your pooch comfortable, such as toys and fenced yards to play in.
What are the top things to do in Shady Side?
There's plenty to discover with the family in Shady Side besides enjoying the comforts and conveniences of your holiday home rental. Don't miss leading attractions like William Paca House and Navy-Marine Corps Memorial Stadium. Want some more ideas? Chesapeake Beach Water Park deserves a place on your Shady Side must-see list.
Why should I book my holiday rental house with Stayz?
When you choose a Stayz holiday home rental, the only people you'll share your space with are whoever you bring with you. It will just be you, your closest companions and the whole property to yourselves. Our flexible cancellation policies also mean you can book your rental house with confidence if your plans change.