Chesterfield holiday rentals

We found 1,749 holiday rentals — enter your dates for availability
Discover a selection of 7 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.

Holiday rentals with weekly discounts – Chesterfield

Showing deals for:13 Nov - 20 Nov

Property grounds
Exterior
Patio Bar Table
Kitchen
Exceptional
(61 reviews)

Need an Elegant Escape?

Augusta

13% off
AU$7,464
for 7 nights, 1 home
AU$1,066 per night
includes taxes & fees
Need an Elegant Escape?
Interior
Property grounds
Private kitchen
Living area
Exceptional
(26 reviews)

Elegant home with pool, fenced yard, full kitchen & theater.

St. Louis

8% off
AU$4,663
for 7 nights, 1 home
AU$666 per night
includes taxes & fees
Elegant home with pool, fenced yard, full kitchen & theater.
backyard at night
basketball court, and side view of property
Front living room
Dining room
Wonderful
(30 reviews)

Elegant house pool, sports, pizza & boat bar, business center, mini theater.

St. Louis

8% off
AU$4,663
for 7 nights, 1 home
AU$666 per night
includes taxes & fees
Elegant house pool, sports, pizza & boat bar, business center, mini theater.
Front door entrance.
Master bedroom, king bed, flat screen TV, and fireplace.
Dining area with fireplace and flat screen TV.
Living room area with cozy seating and flat screen TV.
Exceptional
(144 reviews)

Adorable Two-Person Bungalow nestled in the cozy town of Augusta, MO!

Augusta

13% off
AU$1,701
for 7 nights, 1 cottage
AU$243 per night
includes taxes & fees
Adorable Two-Person Bungalow nestled in the cozy town of Augusta, MO!
Interior
Private kitchen
Terrace/patio
Exterior
Very good
(24 reviews)

Office and 5 BR, Updated Bathrooms, Movie Theater in Creve Coeur

St. Louis

20% off
AU$4,444
for 7 nights, 1 home
AU$635 per night
includes taxes & fees
Office and 5 BR, Updated Bathrooms, Movie Theater in Creve Coeur
Living area
Exterior
Private kitchen
Living area
Exceptional
(26 reviews)

Peaceful and cozy equestrian saturated retreat

Pacific

9% off
AU$1,308
for 7 nights, 1 cabin
AU$187 per night
includes taxes & fees
Peaceful and cozy equestrian saturated retreat
Private indoor pool suite (Heated but NOT air conditioned) w/child safety alarm
This family lives in the back yard, just steps away from the pool suite.
Interior
Cherry red LG washer and dryer in pool suite.
Exceptional
(256 reviews)

Retro Ranch With Private Indoor Pool & Sauna St Louis, MO

Ballwin

7% off
AU$5,213
for 7 nights, 1 home
AU$745 per night
includes taxes & fees
Retro Ranch With Private Indoor Pool & Sauna St Louis, MO
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View from the Deck
Living area
Interior
Exceptional
(99 reviews)

Escape to a private 3BR waterfront retreat on a 7-acre pond near Route 66. Enjoy peaceful views, a fire pit with seating, fishing dock, and spacious living areas. Perfect for relaxing getaways with easy access to St. Louis attractions.

Caseyville

8% off
AU$5,690
for 7 nights, 1 home
AU$813 per night
includes taxes & fees
Escape to a private 3BR waterfront retreat on a 7-acre pond near Route 66. Enjoy peaceful views, a fire pit with seating, fishing dock, and spacious living areas. Perfect for relaxing getaways with easy access to St. Louis attractions.
Interior
Living area
Interior
Room
Exceptional
(5 reviews)

Spacious 4BR Family Home Near Historic St. Charles & STL

St. Charles

8% off
AU$2,580
for 7 nights, 1 home
AU$369 per night
includes taxes & fees
Spacious 4BR Family Home Near Historic St. Charles & STL
Dining
Room
Living area
Living area
Exceptional
(9 reviews)

Charming Historic Retreat in Old Town St. Charles

St. Charles

8% off
AU$2,599
for 7 nights, 1 home
AU$371 per night
includes taxes & fees
Charming Historic Retreat in Old Town St. Charles
Living area
Private kitchen
Exterior detail
Dining
Exceptional
(13 reviews)

Pet and Family Friendly House - Great Location- 30 Minutes to Downtown

Ballwin

8% off
AU$3,855
for 7 nights, 1 home
AU$551 per night
includes taxes & fees
Pet and Family Friendly House - Great Location- 30 Minutes to Downtown
Dining
Private kitchen
Exterior
Room
Exceptional
(40 reviews)

O'Fallon Edge Oasis- 4bd/3bt, Wooded Backyard, Office, Great Family Getaway

O'Fallon

8% off
AU$3,378
for 7 nights, 1 home
AU$483 per night
includes taxes & fees
O'Fallon Edge Oasis- 4bd/3bt, Wooded Backyard, Office, Great Family Getaway
Exterior
Living area
Room
Private kitchen
Exceptional
(34 reviews)

Beautifull *4BDR/ 2Bath *Home Close to Parks and Downtown!

St. Louis

7% off
AU$2,176
for 7 nights, 1 home
AU$311 per night
includes taxes & fees
Beautifull *4BDR/ 2Bath *Home Close to Parks and Downtown!
Kitchen Island
Living room with a sofa
Dining
Living room with a sofa
Exceptional
(16 reviews)

Perfect Getaway @ CWE- Entire Home + Free Parking Near Fox, Universities & More!

St. Louis

8% off
AU$5,251
for 7 nights, 1 home
AU$750 per night
includes taxes & fees
Perfect Getaway @ CWE- Entire Home + Free Parking Near Fox, Universities & More!
Room
Private kitchen
Dining
Living area
Exceptional
(12 reviews)

Close to All STL : Adorable 3BR/2BTH : STL Zoo Forest Park Wash U Hospitals

St. Louis

8% off
AU$2,998
for 7 nights, 1 home
AU$428 per night
includes taxes & fees
Close to All STL : Adorable 3BR/2BTH : STL Zoo Forest Park Wash U Hospitals
Exterior detail
Pool
Exterior detail
Private kitchen
Exceptional
(6 reviews)

Fenton Oasis - private pool and garden

Fenton

8% off
AU$4,399
for 7 nights, 1 home
AU$628 per night
includes taxes & fees
Fenton Oasis - private pool and garden
Private kitchen
Living area
Interior
Interior
Wonderful
(20 reviews)

Bellsworth Bungalow

St. Louis

7% off
AU$1,142
for 7 nights, 1 home
AU$163 per night
includes taxes & fees
Bellsworth Bungalow
Interior
Living area
Living area
Interior
Exceptional
(75 reviews)

Charming Cottage Loft near Soulard and Private Parking

St. Louis

8% off
AU$973
for 7 nights, 1 apartment
AU$139 per night
includes taxes & fees
Charming Cottage Loft near Soulard and Private Parking
Room
Living area
Exterior
Dining
Exceptional
(46 reviews)

St. Charles/St. Peters 3 Bedroom Charmer

St. Charles

8% off
AU$1,586
for 7 nights, 1 home
AU$227 per night
includes taxes & fees
St. Charles/St. Peters 3 Bedroom Charmer
Interior
Dining
Exterior
Living area
Exceptional
(49 reviews)

Serenity Log Inn -Log out and Log Inn to Serenity

Imperial

8% off
AU$1,451
for 7 nights, 1 cabin
AU$207 per night
includes taxes & fees
Serenity Log Inn -Log out and Log Inn to Serenity
Private kitchen
Dining
Interior
Private kitchen
Wonderful
(5 reviews)

3Bed/2Bath perfect for families, couples or groups!

St. Louis

8% off
AU$2,445
for 7 nights, 1 home
AU$349 per night
includes taxes & fees
3Bed/2Bath perfect for families, couples or groups!
Dining
Interior
Private kitchen
Room
Exceptional
(13 reviews)

Charming, Pet friendly, Long stay discounts, 6 miles to Convention Center

St. Peters

8% off
AU$2,884
for 7 nights, 1 home
AU$412 per night
includes taxes & fees
Charming, Pet friendly, Long stay discounts, 6 miles to Convention Center
Interior
Dining
Private kitchen
Living area
Exceptional
(44 reviews)

BEAUTIFUL Historic 3 Bedroom Upscale Guesthouse!!

St. Charles

8% off
AU$4,707
for 7 nights, 1 home
AU$672 per night
includes taxes & fees
BEAUTIFUL Historic 3 Bedroom Upscale Guesthouse!!
Property grounds
Private kitchen
Exterior
Living area
Exceptional
(16 reviews)

The Blue House near Frank Holten State Park / Golf /Lighthouse Restaurant

East St. Louis

16% off
AU$1,516
for 7 nights, 1 home
AU$217 per night
includes taxes & fees
The Blue House near Frank Holten State Park / Golf /Lighthouse Restaurant
  • 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)
  • Creve Coeur Golf Club (7.1 mi / 11.4 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)
  • Grant's Farm (13.7 mi / 22.1 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:

  • Lou Fusz Soccer Complex (4.4 mi / 7.2 km)
  • Kirkwood Park (9.5 mi / 15.3 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)
  • Jewel Box (15.4 mi / 24.8 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.

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