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Chesterfield vacation rentals

We found 1,759 vacation rentals — enter your dates for availability

your current months are April, 2024 and May, 2024.
April 2024
May 2024
Discover a selection of 14 homes and other vacation rentals in Chesterfield that are perfect for your trip. Vacation homes offer the best amenities for you and your friends, family, or even pets, such as parking and air conditioning. At the end of the day, you'll be sure to find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

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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, and its welcoming and scenic location add to the charm. 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

Are you looking for attractions to see during your stay? Venture out of your cozy vacation rental and experience everything that makes Chesterfield a fun place to get away. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • St. Louis Zoo (14.9 mi / 24 km)
  • Chesterfield Sports Fusion (2.8 mi / 4.6 km)
  • Kokomo Joe's Family Fun Center (9.2 mi / 14.7 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 an outdoor enthusiast or just want to appreciate the scenery, you'll be sure to find the perfect setting for your vacation in Chesterfield. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • Lou Fusz Soccer Complex (4.4 mi / 7.2 km)
  • Katy Trail (10.3 mi / 16.6 km)
  • Route 66 State Park (10.8 mi / 17.4 km)
  • Jewel Box (15.4 mi / 24.8 km)
  • Forest Park (15.5 mi / 25 km)
  • Tower Grove Park (16.5 mi / 26.6 km)

Transportation 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 center. If you can't find a flight that works for your travel itinerary, you could book a flight to St. Louis Lambert Intl. Airport (STL), which is 12.1 mi (19.4 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Chesterfield?

The most in-demand types of vacation rentals in Chesterfield are houses. Looking for something different? Vrbo offers a variety of options to match our guests' unique needs, so you'll see vacation 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 vacation rental in Chesterfield?

Property type, length of stay and time of year are some things that can influence the price of a vacation home. Simply click on your travel dates to find your ideal fit. From quaint country cottages to sprawling villas, all Vrbo vacation rentals 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 Vrbo. 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 vacation rentals in Chesterfield?

Pack a travel bag for your pooch because Chesterfield has eight vacation rentals that throw out the welcome mat to pets. Let your happy hound enjoy the family fun at one of our pet-friendly vacation rentals on Vrbo. 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 vacation homes and every day can be a pool day. Simply enter your dates into Vrbo, then check the "pool" filter to find the ideal place for a splashing good time!

What are popular rental amenities in Chesterfield?

A barbecue grill, a garden and a swimming pool top the list of most popular rental amenities in Chesterfield. Whether you're traveling alone, with your better half or a group of friends, Vrbo can help you find a vacation rental that suits your style with all the features you're looking for.

Are there large group vacation rentals 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 vacation rentals in Chesterfield that welcome kids?

With eight family-friendly vacation rentals 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 Center

Are there one-bedroom vacation rentals in Chesterfield?

You'll find three one-bedroom properties in Chesterfield to pick from. A one-bedroom vacation home is an excellent choice if it's only the two of you or if you're vacationing 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 vacation rentals 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 vacation rentals with air conditioning in Chesterfield?

Chesterfield has eight vacation rentals where you can unwind in air-conditioned comfort. To book a stay on Vrbo that has this perk, enter your preferred travel dates and use the filters to select the "air conditioning" box.

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