Photo by Ronanne Vinson

Chesapeake Beach rentals with pool

We found 89 rentals with pool — enter your dates for availability

Find spaces that suit your style

  • 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 rental with a pool in Chesapeake Beach?
A range of factors will determine the price of a holiday rental with a pool in Chesapeake Beach, such as the size of the property and how long and when you plan to stay. All you need to do is key in your holiday dates and preferences to find a house where you can splash around in.
When is the best time to book a holiday rental with a pool in Chesapeake Beach?
The weather conditions will help you choose when it's the perfect time to plan a poolside adventure. Many visitors to Maryland book a Chesapeake Beach holiday rental with a pool in March, when average temperatures range from 4ºC to 10ºC.
What holiday rentals with a pool in Chesapeake Beach have nice views?
Bookabach makes it simple to find a stay with stunning views and access to poolside relaxation. You can use our "Location" filter to narrow down the kind of area you prefer to be in, and the scenery you want to wake up to, while searching for holiday rentals with a pool in Chesapeake Beach.
Are there holiday rentals with a private pool in Chesapeake Beach?
Although there aren't any holiday rentals with a private pool in Chesapeake Beach, you will find options that have what you need to be nice and comfortable. Choosing a Bookabach property means you'll have more privacy, space and home comforts compared to a standard hotel. And with our handy filter tool, you can narrow your search by the exact amenities you want, whether that's a fireplace or backyard.
What are the top things to do in Chesapeake Beach?
Breezy Point Beach, Chesapeake Beach Water Park and Chesapeake Beach Railway Museum are places to include on your itinerary while staying at a holiday home rental with a pool in Chesapeake Beach. The only thing that beats visiting this city's top attractions? Lounging poolside with the fam after a fun-filled day of tours and activities.
Why should I book my holiday rental with a pool with Bookabach?
Bookabach provides first-rate customer support from the second you book until your trip is over, so every aspect of your holiday is enjoyable and hassle-free. It's all part of our Book with Confidence Guarantee, which also includes deposit and payment protection and flexible cancellation policies. Another good thing about us? You can use our filters to fine-tune your search by price, location, amenities and more. Whether you want a pet-friendly space or a countryside getaway for the family, we've got holiday rentals with a pool that match your exact needs and style.