Photo by Michelle E

Chesterfield holiday rentals

We found holiday rentals — enter your dates for availability

Discover a selection of 11 homes and other holiday rentals in Chesterfield that are perfect for your trip. Holiday homes offer the amenities that you expect for your family, friends or furry companion, such as parking and a TV. At the end of the day, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

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

The friendly city of Chesterfield awaits you

Enjoy the museums and other features of Chesterfield. This city's shopping, restaurants and sporting events attract many visitors, as does its welcoming and scenic location. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Chesterfield

Do you want to discover attractions to see in the area? Venture out of your holiday home and experience everything that makes Chesterfield a one-of-a-kind holiday spot. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • St. Louis Zoo (14.9 mi / 24 km)
  • Chesterfield Sports Fusion (2.8 mi / 4.6 km)
  • Missouri Bluffs Golf Course (6.6 mi / 10.6 km)
  • Hidden Valley Ski Resort (9.9 mi / 15.9 km)
  • Six Flags St. Louis (11.7 mi / 18.9 km)
  • Chandler Hill Vineyards (12.9 mi / 20.8 km)

Exploring the natural features in Chesterfield

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Chesterfield is a great place to spend some time outside. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Sophia M. Sachs Butterfly House (1.3 mi / 2 km)
  • Lou Fusz Soccer Complex (4.4 mi / 7.2 km)
  • Lone Elk Park (9 mi / 14.5 km)
  • Katy Trail (10.3 mi / 16.6 km)
  • August A. Busch Memorial Conservation Area (11.1 mi / 17.8 km)
  • Laumeier Sculpture Park (11.3 mi / 18.1 km)

Transport options to and around Chesterfield

The nearest airport is in St. Louis, MO (SUS-Spirit of St. Louis), located 4.4 mi (7 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Lambert-St. Louis International Airport (STL), which is 12.1 mi (19.4 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Chesterfield?
The most in-demand types of holiday homes in Chesterfield are houses. Looking for something different? Stayz offers a variety of options to match our guests’ unique needs, so you’ll see holiday properties in loads of shapes and sizes. The perfect fit is waiting for you — grab yours today.
How much does it cost to rent a holiday home in Chesterfield?
Property type, length of stay and time of year are some things that can influence the price of a holiday home. Simply click on your travel dates to find your ideal fit. From quaint country cottages to sprawling villas, all Stayz holiday homes provide amazing value.
How much does it cost to rent a beach house in Chesterfield?
When you travel and the size and style of the property will determine the cost of your beachside escape. Click on your Chesterfield travel dates to see your options on Stayz. Can’t live without a hot tub? Use the filters to pick the features and amenities you want in your beach house.
Are there pet-friendly holiday homes in Chesterfield?
Pack a travel bag for your pooch because Chesterfield has eight holiday homes that throw out the welcome mat to pets. Let your happy hound enjoy the family fun at one of our pet-friendly holiday homes on Stayz. Simply enter your travel dates and destination, then check the “Pets allowed” filter box.
Can I rent a house with a pool in Chesterfield?
Dig out your swimwear and inflatable unicorn, because there are three houses with a private pool in Chesterfield. Unwind at one of these terrific holiday homes and every day can be a pool day. Simply enter your dates into Stayz, then check the “pool” filter to find the ideal place for a splashing good time!
What are popular home amenities in Chesterfield?
A barbecue grill, a garden and a swimming pool top the list of most popular home amenities in Chesterfield. Whether you’re travelling alone, with your better half or a group of friends, Stayz can help you find a holiday home that suits your style with all the features you’re looking for.
Are there large group holiday homes in Chesterfield?
With four Chesterfield properties that can accommodate five or more people, you can bring a few extra family members or pals along. Whether you’re planning a casual get-together or a special celebration, we’ll help you book a comfortable space to fit the occasion.
Are there holiday homes in Chesterfield that welcome kids?
With eight family-friendly holiday homes available in Chesterfield, there’s never been a better time to introduce the kiddos to the pleasures of travel. Simply check our “Properties good for families” filter to look for stays that come with amenities perfect for families on the move, like full kitchens, swimming pools, bunk beds and entertainment areas.
What are the top attractions for families in Chesterfield?
You’ll find lots of cool things to see and do with the family in Chesterfield, such as:

  • Chesterfield Sports Fusion
  • Museum of Transportation
  • Kokomo Joes Family Fun Centre

Are there one-bedroom holiday homes in Chesterfield?
You’ll find three one-bedroom properties in Chesterfield to pick from. A one-bedroom holiday home is an excellent choice if it’s only the two of you or if you’re holidaying solo. Add in more convenience, privacy and space compared to a regular hotel, and you’ll be sure to have a trip to remember.
Can I find two-bedroom holiday homes in Chesterfield?
Choose from five two-bedroom homes in Chesterfield. Put your little ones in the second room or fill it with a couple of your best buddies. There’s ample space for whoever’s fortunate enough to be joining in on the fun.
How can I find holiday homes with air conditioning in Chesterfield?
Chesterfield has eight holiday homes where you can unwind in air-conditioned comfort. To book a stay on Stayz that has this perk, enter your preferred travel dates and use the filters to select the “air conditioning” box.
How old do you have to be to rent a holiday home in Chesterfield?
The minimum required age is typically 16, 18 or 21. It can change across properties on Stayz, so check the rules of your preferred Chesterfield holiday home before making a booking.
How long can I rent a holiday home in Chesterfield for?
The amount of time you can book a Chesterfield holiday home for depends on the property. Simply enter your travel dates to browse available options that offer extended stays. They come with everything you need to make your extended getaway more convenient and comfortable, like laundries and air conditioning. Some Stayz holiday properties may also offer weekly or monthly discounted prices, so you can have a longer stay for less.

Explore destinations around Chesterfield

More Holiday Rentals ideas

Denmark Holiday Rentals
Standard Link for Denmark
Maitland Holiday Rentals
Standard Link for Maitland
Berlin Holiday Rentals
Standard Link for Berlin
Gold Coast Holiday Rentals
Standard Link for Gold Coast
Tuggeranong Holiday Rentals
Standard Link for Tuggeranong
Terrigal Holiday Rentals
Standard Link for Terrigal
Crowdy Head Holiday Rentals
Standard Link for Crowdy Head
Kansas City Holiday Rentals
Standard Link for Kansas City
Penrith Holiday Rentals
Standard Link for Penrith
Central Coast Holiday Rentals
Standard Link for Central Coast
Jimboomba Holiday Rentals
Standard Link for Jimboomba
Toowoomba Holiday Rentals
Standard Link for Toowoomba
Grandview Holiday Rentals
Standard Link for Grandview
Portland Holiday Rentals
Standard Link for Portland
Mermaid Beach Holiday Rentals
Standard Link for Mermaid Beach
Mount Dandenong Holiday Rentals
Standard Link for Mount Dandenong
Warwick Holiday Rentals
Standard Link for Warwick
St. Louis Holiday Rentals
Standard Link for St. Louis
Glenelg Holiday Rentals
Standard Link for Glenelg
Frankton Holiday Rentals
Standard Link for Frankton
Airlie Beach Holiday Rentals
Standard Link for Airlie Beach
South Australia Holiday Rentals
Standard Link for South Australia
Monkey Mia Holiday Rentals
Standard Link for Monkey Mia
Darwin Holiday Rentals
Standard Link for Darwin
Bellingen Holiday Rentals
Standard Link for Bellingen
Rome Holiday Rentals
Standard Link for Rome
Moana Beach Holiday Rentals
Standard Link for Moana Beach
Nerang Holiday Rentals
Standard Link for Nerang
Werribee Holiday Rentals
Standard Link for Werribee

People also search for

Penang Villas
Standard Link for Penang