What are the top rated Cottage Rentals in Shady Side?

There are a lot of options in Shady Side. If you plan on staying in the Shady Side area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Shady Side: <a href="/property/5-years-young-stunning-home-with-water-view/HA-3212469760" class="class="static-page-link"">5-years young STUNNING home with water view!</a> <a href="/property/peaceful-2-bedroom-2-bathroom-house-with-wifi-and-ac-in-serene-shady-side/HA-3214578169" class="class="static-page-link"">Peaceful 2-bedroom/2-bathroom house with WiFi and AC in serene Shady Side</a> <a href="/property/home-w-beach-access-boat-slip-basketball-court/HA-3214701941" class="class="static-page-link"">Home w/Beach Access Boat Slip Basketball Court</a> <a href="/property/pier-joy-3br-waterfront-home-w-private-dock/HA-3212542393" class="class="static-page-link"">&#34;PIER JOY!&#34; - 3BR WATERFRONT HOME W/PRIVATE DOCK</a> <a href="/property/waterfront-home-on-the-chesapeake-bay/HA-3213081348" class="class="static-page-link"">Waterfront Home on the Chesapeake Bay!</a> <a href="/property/spacious-6-bedroom-country-house-on-the-water-in-beautiful-shady-side-with-wifi/HA-3213875726" class="class="static-page-link"">Spacious 6-bedroom country house on the water in beautiful Shady Side with WiFi</a> <a href="/property/bay-views-with-kayaks-bikes-fire-pit-crabbing-and-more/HA-3213298374" class="class="static-page-link"">Bay views with kayaks, bikes, fire pit, crabbing and more</a> <a href="/property/3br-home-near-the-beach-with-bikes/BC-10572177" class="class="static-page-link"">3BR Home Near the Beach with Bikes</a> <a href="/property/sunset-cottage-west-river-access-and-views/HA-3214940848" class="class="static-page-link"">Sunset Cottage - West River Access and Views!</a> <a href="/property/3br-home-near-the-beach-w-bikes/HA-12120224510" class="class="static-page-link"">3BR Home Near the Beach w/Bikes</a>

How much does it cost to rent a cottage in Shady Side?

The average cost for a cottage rental in Shady Side is $275 per night. 7oceanvacation has a wide list of great cottages near Shady Side that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Shady Side that allow pets?

Yes, here are the top cottage rentals in Shady Side that allow you to bring your pet: Tranquil Waterfront Cottage in Shady Side - 50 minutes to DC Peaceful 2-bedroom/2-bathroom house with WiFi and AC in serene Shady Side 3BR Home Near the Beach with Bikes Home w/Beach Access Boat Slip Basketball Court The Bay House <a href="/all/usa/maryland/shady-side" class="class="static-page-link"">See all pet-friendly vacation rentals in Shady Side on 7oceanvacation</a>

Do you have any rental cottages in Shady Side that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Shady Side to find one that works for you.

Are there quality cottages in Shady Side that have indoor swimming pools?

As of 2026, the data from 7oceanvacation shows that there are Over 1 private swimming pools or cottages with indoor pools in the Shady Side area along with other great amenities.

Shady Side Cottage Rentals By Owner

Tranquil Waterfront Cottage in Shady Side - 50 minutes to DC

From US $275

New

Cottage

Tranquil Waterfront Cottage in Shady Side - 50 minutes to DC

Air Conditioner
Parking
TV

Shady Side Cottage Rentals & Holiday Homes

Find the best cottages in Shady Side - We found 1 exact matches

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