Photo by Michelle E

Chesterfield rentals with pool

We found 227 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

Are there any holiday rentals with a pool in Chesterfield?
Choose one of our 227 holiday rentals with a pool in Chesterfield and get ready for cannonball competitions. Clarkson Valley, Winchester and Harvester are among the city's most sought-after neighbourhoods.
How much does it cost to stay in a holiday rental with a pool in Chesterfield?
A range of factors will influence how much you pay for a holiday rental with a pool in Chesterfield, such as the size of the property and how long and when you're staying. All you need to do is key in your travel dates and preferences to find a house where you can have some poolside fun.
When is the best time to book a holiday rental with a pool in Chesterfield?
Consider booking your poolside escape to Chesterfield in August, when the average daily temperature ranges between 20ºC and 31ºC. This is the most popular time for guests to stay in a holiday rental with a pool in this well-known destination, which is located in Ozarks.
What holiday rentals with a pool in Chesterfield have nice views?
If your perfect getaway involves poolside fun and picturesque outlooks, you'll find Chesterfield holiday rentals with a pool that offer exactly that. Book one with views of historic areas and dive headfirst into a blissful holiday experience.
Are there holiday rentals with a private pool in Chesterfield?
Although there aren't any holiday rentals with a private pool in Chesterfield, you will find stays that have everything you need to be comfortable. Booking a Stayz property means you'll have more space, privacy and home comforts compared to a regular hotel. And with our handy filter tool, you can fine-tune your search by the amenities or features you're after, whether that's a barbecue or patio.
What are the top things to do in Chesterfield?
You'll always find something fun to do with the crew when you check into a holiday home rental with a pool in Chesterfield. Get out and explore leading attractions like Six Flags St. Louis, Magic House - St. Louis Children's Museum and Saint Louis Galleria Mall, then come back to kick back and relax by the water.
Why should I book my holiday rental with a pool with Stayz?
We provide first-rate customer support from the minute you book until your adventure is done, 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, amenities, location and more. Whether you're looking for a pet-friendly property or a countryside getaway for the family, we've got holiday rentals with a pool that match your exact needs and style.