Top Chesapeake City rentals with pool or private pool - Maryland

Explore Chesapeake City rentals with pools

Historic Chesapeake City Stay

Sleeps 2 · 1 bedroom · 1 bathroom

12 Bedroom Waterfront Historic 1920 Mansion! Pool, hot tub and 400 acres!

Sleeps 30 · 12 bedrooms · 8+ bathrooms

Top rated rentals with pools - Chesapeake City

Premier Host

Incredible view and hospitality!

House is easy to find, backed right up to the water so you get to wake up to gorgeous sunsets! The home is well furnished with everything you could need and on top of that it’s beautiful. Located near some great seafood restaurants and local shops.

Destiny C.

Stayed Feb 2021

Find spaces that suit your style

House

Condo/Apartment

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to stay in a holiday home with a pool in Chesapeake City?

A number of factors will determine how much you pay for a holiday home with a pool in Chesapeake City, such as the size of the property and how long and when you plan to stay. All you have to do is key in your holiday dates and any preferences to find a house where you can have some poolside fun.

When is the best time to book a holiday home with a pool in Chesapeake City?

If you want to enjoy Chesapeake City at one of its busiest times, plan your trip for July. That's when temperatures range from around 20ºC (20ºC) to 30ºC (30ºC), and when the majority of Stayz guests book a holiday home with a pool here. Of course, there are other excellent times to get away to this part of Maryland, so do some homework into which season or month best fits your plans.

What holiday homes with a pool in Chesapeake City have nice views?

Stayz has some impressive holiday homes with a pool in Chesapeake City, including houses with views of historic areas. When you aren't touring the sights, relax by going for a swim and gaze at scenes that are their own attraction.