Top Shady Side rentals with pool or private pool - Maryland

Explore Shady Side rentals with pools

Premier Host

Sweet Bamboo Beach Cottage

Sleeps 6 · 3 bedrooms · 1 bathroom

Premier Host

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Sleeps 16 · 5 bedrooms · 4+ bathrooms

Top rated rentals with pools - Shady Side

Premier Host

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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Frequently asked questions

How much does it cost to stay in a holiday home with a pool in Shady Side?

Exactly where you stay, when you decide to travel and your trip length will influence how much you pay for a holiday home with a pool in Shady Side. Enter your travel dates on Stayz, then lock in the right one for you and prepare to make a splash.

When is the best time to book a holiday home with a pool in Shady Side?

July is when the majority of guests book a holiday home with a pool in Shady Side, which is in Southern Maryland. On average, temperatures range from 22ºC (22ºC) to 30ºC (30ºC) during this month.

What holiday homes with a pool in Shady Side have nice views?

Stayz makes it easy to find a stay with striking views and access to poolside relaxation. Use the "Location" filter to narrow down the kind of area you prefer to be in, and the vistas you like to surround yourself with, while searching for holiday homes with a pool in Shady Side.