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

1. 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, (3 reviews)
"This is a beautiful home in a quiet beautiful setting. The host was great to work with and responded quickly to any questions we had. Would highly recommend!"
United States
Jennifer M.
The price is AU$564
includes taxes & fees
7 Sept - 8 Sept
3+ acres, fast wi-fi, garage parking, Koi pond

2. 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$98
includes taxes & fees
1 Oct - 2 Oct
2 Queen Beds | Non-Smoking, Kitchen

3. 1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
Westport
9.6 out of 10, Exceptional, (41 reviews)
"Great spot!"
United States
Anonymous traveller
The price is AU$98
includes taxes & fees
1 Oct - 2 Oct
1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

4. Historic Main Street Studio | Dog-Friendly

Historic Main Street Studio | Dog-Friendly
St. Charles Historic District
9.2 out of 10, Wonderful, (37 reviews)
"Had a wonderful stay. It was a Monday night so parking was very easy and the room was clean and comfortable. I would recommend this place 100% "
United States
Sarah C.
The price is AU$290
includes taxes & fees
6 Sept - 7 Sept
Historic Main Street Studio | Dog-Friendly

5. 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, (86 reviews)
"Quaint and quiet, with easy access to downtown St Charles."
United States
Jeffrey E.
The price is AU$362
includes taxes & fees
14 Sept - 15 Sept
Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!

6. Historic 1805 Main Street 2BR

Historic 1805 Main Street 2BR
St. Charles Historic District
9.6 out of 10, Exceptional, (42 reviews)
"The location is excellent. "
United States
McRay H.
The price is AU$519
includes taxes & fees
20 Sept - 21 Sept
Historic 1805 Main Street 2BR

7. St. Charles 1860's Gem - Sleeps 6!

St. Charles 1860's Gem - Sleeps 6!
St. Charles Historic District
9.8 out of 10, Exceptional, (163 reviews)
"Very nice very clean property. Very much enjoyed our stay"
United States
Joe R.
The price is AU$393
includes taxes & fees
8 Sept - 9 Sept
St. Charles 1860's Gem - Sleeps 6!

8. Walk to Main | Pet-Friendly Yard & Workspace

Walk to Main | Pet-Friendly Yard & Workspace
St. Charles Historic District
10.0 out of 10, Exceptional, (11 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
7 Sept - 8 Sept
Walk to Main | Pet-Friendly Yard & Workspace

9. Amazing Renovated Historic Loft on Main Street

Amazing Renovated Historic Loft on Main Street
St. Charles Historic District
10.0 out of 10, Exceptional, (68 reviews)
"Lovely accommodations, very clean, well equipped, great location. "
United States
Emily B.
The price is AU$367
includes taxes & fees
7 Sept - 8 Sept
Amazing Renovated Historic Loft on Main Street

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

Charming open 4bd and screen-in porch! Sleeps 10!
Saint Charles
9.0 out of 10, Wonderful, (50 reviews)
"Great property, plenty of space, was very clean!"
United States
Will M.
Charming open 4bd and screen-in porch! Sleeps 10!

11. Prime Loft of Main Street

Prime Loft of Main Street
St. Charles Historic District
9.8 out of 10, Exceptional, (116 reviews)
"Host was great. The cutest place in the perfect spot! "
United States
Anonymous traveller
The price is AU$367
includes taxes & fees
7 Sept - 8 Sept
Prime Loft of Main Street

12. 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$392
includes taxes & fees
13 Sept - 14 Sept
Great for Business Travelers! Comfortable Suite in St. Louis | BBQ Area

13. Stunning Minimalist Gem | Fenced Backyard + W/D

Stunning Minimalist Gem | Fenced Backyard + W/D
Princeton Heights
10.0 out of 10, Exceptional, (24 reviews)
"Nice area, very well kept house and easy check-in process. Good parking"
United States
Christopher
The price is AU$253
includes taxes & fees
9 Sept - 10 Sept
Stunning Minimalist Gem | Fenced Backyard + W/D

14. The Lofts of North Main Street

The Lofts of North Main Street
St. Charles Historic District
9.6 out of 10, Exceptional, (188 reviews)
"It was great! Clean and great communication with host."
United States
Natalie H.
The price is AU$367
includes taxes & fees
7 Sept - 8 Sept
The Lofts of North Main Street

15. Historic Main St. Customs House Upstairs Apartment

Historic Main St. Customs House Upstairs Apartment
St. Charles Historic District
9.6 out of 10, Exceptional, (39 reviews)
"Lovely place to stay!"
United States
Margaret A.
The price is AU$500
includes taxes & fees
6 Sept - 7 Sept
Historic Main St. Customs House Upstairs Apartment

16. New Remodel in St. Charles - Sleeps 10! New patio! Large Fenced-in backyard!

New Remodel in St. Charles - Sleeps 10! New patio! Large Fenced-in backyard!
St. Charles Historic District
9.6 out of 10, Exceptional, (79 reviews)
"Spacious house and plenty of room in the long drive for everyone's cars which is rare! Would stay at again!"
United States
Matthew B.
New Remodel in St. Charles - Sleeps 10! New patio! Large Fenced-in backyard!

17. Stunning 1890's Home - Sleeps 8!

Stunning 1890's Home - Sleeps 8!
St. Charles Historic District
10.0 out of 10, Exceptional, (133 reviews)
"Super cute property, fantastic location. Very well maintained and clean, would definitely stay here again. "
United States
Jason T.
The price is AU$594
includes taxes & fees
9 Sept - 10 Sept
Stunning 1890's Home - Sleeps 8!

18. Spacious, 3 bedroom home, finished basement on quiet court

Spacious, 3 bedroom home, finished basement on quiet court
St. Peters
9.8 out of 10, Exceptional, (54 reviews)
"It was a perfect choice for our family to celebrate Christmas. "
United States
Leanne S.
The price is AU$509
includes taxes & fees
15 Sept - 16 Sept
Spacious, 3 bedroom home, finished basement on quiet court

19. 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, (50 reviews)
"The house was immaculately clean and beds were extremely comfortable!"
United States
Anna M.
The price is AU$378
includes taxes & fees
27 Sept - 28 Sept
Convenience 2 Bedroom House to Explore All of St Louis

20. Elegant Minimalist Gem w/ Private backyard, W/D

Elegant Minimalist Gem w/ Private backyard, W/D
Princeton Heights
9.4 out of 10, Exceptional, (27 reviews)
"Brandon was awesome and the neighborhood is fun with lots of terrific restaurants. "
United States
Leslie H.
The price is AU$253
includes taxes & fees
9 Sept - 10 Sept
Elegant Minimalist Gem w/ Private backyard, W/D
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$98 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?

4BR 2BA Modern Family Home with Private Heated Inground Pool Open March 1-Nov11: This holiday home rental outside of Chesterfield offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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. Other places in town to visit include The Factory and St. Louis Premium Outlets.

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.