A town with a prominent church spire, residential buildings, and a hill in the background.

Chesterfield Holiday Rentals

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Our top choices for Chesterfield holiday rentals

3+ acres, fast wi-fi, garage parking, Koi pond

3+ acres, fast wi-fi, garage parking, Koi pond
Wildwood
10.0 out of 10, Exceptional, (1 review)
"Absolutely stunning home! Beautiful, love the koy pond!"
United States
Bailey G.
3+ acres, fast wi-fi, garage parking, Koi pond

2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Westport
9.8 out of 10, Exceptional, (38 reviews)
"Fantastic place!"
United States
Anonymous traveller
The price is AU$154
includes taxes & fees
23 July - 24 July
2 Queen Beds | Non-Smoking, Kitchen

Chic 1- Queen Bed, Non Smoking-Near Airport, Kitchen, Twin Bed

Chic 1- Queen Bed, Non Smoking-Near Airport, Kitchen, Twin Bed
St. Louis
9.0 out of 10, Wonderful, (13 reviews)
"This was absolutely perfect and reasonable pricing I surely will be back "
United States
David G.
The price is AU$147
includes taxes & fees
9 Aug - 10 Aug
Chic 1- Queen Bed, Non Smoking-Near Airport, Kitchen, Twin Bed

1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen
Westport
9.8 out of 10, Exceptional, (41 reviews)
"I really enjoy it here!"
United States
Anonymous traveller
The price is AU$138
includes taxes & fees
21 July - 22 July
1 Queen Bed | Non-Smoking, Kitchen

Duplex Hideaway in St. Charles, MO

Duplex Hideaway in St. Charles, MO
St. Charles Historic District
9.8 out of 10, Exceptional, (7 reviews)
"I will stay here again. It was a great location for my visit. Lots of room and amenities. Highly recommend this location if you are visiting the St Louis area. Barely a mile to get to Hwy 70, so easy access to St Louis, St Peter's, Wentzville etc. Maybe two blocks from Historic St Charles and Ameristar Casino."
United States
Karen M.
The price is AU$390
includes taxes & fees
20 July - 21 July
Duplex Hideaway in St. Charles, MO

1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
Westport
9.8 out of 10, Exceptional, (40 reviews)
"Great spot!"
United States
Anonymous traveller
The price is AU$146
includes taxes & fees
22 July - 23 July
1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!

Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!
St. Charles Historic District
9.6 out of 10, Exceptional, (80 reviews)
"Great location and beautiful place. Had a wonderful time. "
United States
Ernest R.
The price is AU$355
includes taxes & fees
20 July - 21 July
Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!

Great for Business Travelers! Comfortable Suite in St. Louis | BBQ Area

Great for Business Travelers! Comfortable Suite in St. Louis | BBQ Area
Westport
10.0 out of 10, Exceptional, (5 reviews)
"Everything from the staff to the amenities to the rooms were amazing! Definitely recommend staying here! "
Canada
Lashon C.
The price is AU$414
includes taxes & fees
2 Aug - 3 Aug
Great for Business Travelers! Comfortable Suite in St. Louis | BBQ Area

St. Charles 1860's Gem - Sleeps 6!

St. Charles 1860's Gem - Sleeps 6!
St. Charles Historic District
9.8 out of 10, Exceptional, (158 reviews)
"Very nice historical place "
United States
Shawntell C.
The price is AU$404
includes taxes & fees
22 July - 23 July
St. Charles 1860's Gem - Sleeps 6!

Convenience 2 Bedroom House to Explore All of St Louis

Convenience 2 Bedroom House to Explore All of St Louis
University City
9.8 out of 10, Exceptional, (49 reviews)
"The house was immaculately clean and beds were extremely comfortable!"
United States
Anna M.
The price is AU$413
includes taxes & fees
20 July - 21 July
Convenience 2 Bedroom House to Explore All of St Louis

Historic Main St. Customs House Upstairs Apartment

Historic Main St. Customs House Upstairs Apartment
St. Charles Historic District
9.6 out of 10, Exceptional, (38 reviews)
"Lovely place to stay!"
United States
Margaret A.
The price is AU$567
includes taxes & fees
20 July - 21 July
Historic Main St. Customs House Upstairs Apartment

The Lofts of North Main Street

The Lofts of North Main Street
St. Charles Historic District
9.6 out of 10, Exceptional, (180 reviews)
"Great place to stay. Our go to when visiting St.Charles or STL"
United States
jeramy p.
The price is AU$373
includes taxes & fees
20 July - 21 July
The Lofts of North Main Street

Charming open 4bd and screen-in porch! Sleeps 10!

Charming open 4bd and screen-in porch! Sleeps 10!
Saint Charles
9.2 out of 10, Wonderful, (47 reviews)
"Everything about the property was great. Very roomy and felt like home. "
United States
Dan R.
The price is AU$803
includes taxes & fees
21 July - 22 July
Charming open 4bd and screen-in porch! Sleeps 10!

Prime Loft of Main Street

Prime Loft of Main Street
St. Charles Historic District
9.8 out of 10, Exceptional, (112 reviews)
"Host was great. The cutest place in the perfect spot! "
United States
Anonymous traveller
The price is AU$397
includes taxes & fees
20 July - 21 July
Prime Loft of Main Street

Amazing Renovated Historic Loft on Main Street

Amazing Renovated Historic Loft on Main Street
St. Charles Historic District
10.0 out of 10, Exceptional, (65 reviews)
"Lovely accommodations, very clean, well equipped, great location. "
United States
Emily B.
The price is AU$400
includes taxes & fees
3 Aug - 4 Aug
Amazing Renovated Historic Loft on Main Street

Value Suites Extended Stay - St Louis

Value Suites Extended Stay - St Louis
3.0 star property
Westport
7.0 out of 10, Good, (1,110 reviews)
"We’ve stayed here twice before and have always been pleased with everything. Very good hotel close to what we need."
United States
Timothy
The price is AU$752
includes taxes & fees
3 Aug - 4 Aug
Value Suites Extended Stay - St Louis

6655 1N | Elegance Near the St. Louis Arch

6655 1N | Elegance Near the St. Louis Arch
Dogtown
8.0 out of 10, Very good, (27 reviews)
"Listing was consistent with images and the price and location were great. Apartment was clean but furniture and linens are worn. There were only 3 towels and we stayed several days so that was a challenge. Location made up for that mostly as we walked to the zoo and forest park easily. My biggest complaint was the apartment smelled strongly of smoke. I don’t think anyone lives there so that was unusual to me, but there were several cigarette butts on the stairs and back porch nearby and we saw a...
United States
Michelle
The price is AU$218
includes taxes & fees
20 July - 21 July
6655 1N | Elegance Near the St. Louis Arch

Stunning 1890's Home - Sleeps 8!

Stunning 1890's Home - Sleeps 8!
St. Charles Historic District
10.0 out of 10, Exceptional, (127 reviews)
"Super cute property, fantastic location. Very well maintained and clean, would definitely stay here again. "
United States
Jason T.
The price is AU$615
includes taxes & fees
10 Aug - 11 Aug
Stunning 1890's Home - Sleeps 8!

Stunning Minimalist Gem | Fenced Backyard + W/D

Stunning Minimalist Gem | Fenced Backyard + W/D
Princeton Heights
10.0 out of 10, Exceptional, (21 reviews)
"Good host and amenities."
United States
Adam N.
The price is AU$281
includes taxes & fees
20 July - 21 July
Stunning Minimalist Gem | Fenced Backyard + W/D

Villa in Eureka 3.9 miles to Six Flags & 3.2 miles to Hidden Valley Ski Resort!

Villa in Eureka 3.9 miles to Six Flags & 3.2 miles to Hidden Valley Ski Resort!
Eureka
8.8 out of 10, Excellent, (71 reviews)
"This was convenient and the hosts were great to work with."
United States
Tracy F.
The price is AU$398
includes taxes & fees
26 July - 27 July
Villa in Eureka 3.9 miles to Six Flags & 3.2 miles to Hidden Valley Ski Resort!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chesterfield Hotel Reviews

Find out more about Chesterfield

Everything you need to know about Chesterfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesterfield holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chesterfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterfield holiday rentals we have selected for you start as low as AU$138 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chesterfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesterfield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesterfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Chesterfield?

Yes, there are holiday rentals in Chesterfield close to St. Louis Carousel, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Chesterfield. Make sure you have time to check out the sporting events and museums during your trip.

What are some of the best holiday rentals that Chesterfield has to offer?

Pet-Friendly Soulard Townhouse · 2BR/2BA · Parking + Rooftop Deck: This holiday home rental outside of Chesterfield offers a fireplace, a balcony and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of garden in this rental home to help you unwind.

How many holiday rentals are there in Chesterfield?

Choose from 8 Expedia holiday rentals in Chesterfield for a memorable holiday.

What can I see and do in Chesterfield?

Family-friendly attractions include Sky Zone Indoor Trampoline Park - St. Louis and Myseum, whereas Missouri River and Sophia M. Sachs Butterfly House are a couple of great spots to enjoy the outdoors. While in the area, you can also visit popular places such as Six Flags St. Louis and St. Louis Zoo.

What are holiday rentals like in Chesterfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesterfield. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a family getaway.