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

Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Chesterfield vacation rentals

1 bedroom, WiFi (free)

1. 1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen
Westport
9.6 out of 10, Exceptional, (42 reviews)
"I really enjoy it here!"
United States
Anonymous traveler
The price is AED 249
AED 288 total
includes taxes & fees
25 Aug - 26 Aug
1 Queen Bed | Non-Smoking, Kitchen
Property grounds

2. 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 AED 312
AED 410 total
includes taxes & fees
4 Sep - 5 Sep
Chic 1- Queen Bed, Non Smoking-Near Airport, Kitchen, Twin Bed
Interior

3. Spacious 2 Bedroom Townhome

Spacious 2 Bedroom Townhome
Saint Charles
8.0 out of 10, Very Good, (18 reviews)
"Quiet area and clean rooms"
United States
Chelsie H.
The price is AED 389
AED 1,099 total
includes taxes & fees
16 Aug - 17 Aug
Spacious 2 Bedroom Townhome
Interior

4. 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 traveler
The price is AED 278
AED 323 total
includes taxes & fees
10 Aug - 11 Aug
2 Queen Beds | Non-Smoking, Kitchen
1 bedroom, WiFi (free)

5. 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 traveler
The price is AED 263
AED 306 total
includes taxes & fees
10 Aug - 11 Aug
1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
Smart TV, stereo

6. 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)
"Quaint and quiet, with easy access to downtown St Charles."
United States
Jeffrey E.
The price is AED 422
AED 889 total
includes taxes & fees
10 Aug - 11 Aug
Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!
Interior

7. 2 Queen Beds | Mobil Access Tub Nsmk Kitchen

2 Queen Beds | Mobil Access Tub Nsmk Kitchen
Westport
10.0 out of 10, Exceptional, (44 reviews)
"Great place to stay!"
United States
Anonymous traveler
The price is AED 278
AED 323 total
includes taxes & fees
11 Aug - 12 Aug
2 Queen Beds | Mobil Access Tub Nsmk Kitchen
1 bedroom, WiFi, bed sheets

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

Walk to Main | Pet-Friendly Yard & Workspace
St. Charles Historic District
9.8 out of 10, Exceptional, (8 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 AED 595
AED 1,184 total
includes taxes & fees
20 Aug - 21 Aug
Walk to Main | Pet-Friendly Yard & Workspace
Interior

9. Cottage on Main st- Low Cleaning Fee

Cottage on Main st- Low Cleaning Fee
St. Charles Historic District
10.0 out of 10, Exceptional, (9 reviews)
"Good location. Decorated very nicely. "
United States
Debbie A.
The price is AED 430
AED 1,073 total
includes taxes & fees
18 Aug - 19 Aug
Cottage on Main st- Low Cleaning Fee
Exterior

10. 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 AED 377
AED 819 total
includes taxes & fees
10 Aug - 11 Aug
Historic Main Street Studio | Dog-Friendly
Interior

11. Amazing Renovated Historic Loft on Main Street

Amazing Renovated Historic Loft on Main Street
St. Charles Historic District
10.0 out of 10, Exceptional, (67 reviews)
"Lovely accommodations, very clean, well equipped, great location. "
United States
Emily B.
The price is AED 459
AED 956 total
includes taxes & fees
10 Aug - 11 Aug
Amazing Renovated Historic Loft on Main Street
Coffee/tea maker, fridge, microwave, oven

12. 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 AED 643
AED 1,521 total
includes taxes & fees
20 Aug - 21 Aug
Historic Main St. Customs House Upstairs Apartment
TV, books

13. 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 AED 479
AED 1,009 total
includes taxes & fees
10 Aug - 11 Aug
St. Charles 1860's Gem - Sleeps 6!
Coffee/tea maker, fridge, microwave, oven

14. 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 AED 595
AED 1,459 total
includes taxes & fees
11 Aug - 12 Aug
Historic 1805 Main Street 2BR
Dining

15. 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 AED 850
AED 1,115 total
includes taxes & fees
6 Sep - 7 Sep
Great for Business Travelers! Comfortable Suite in St. Louis | BBQ Area
Interior

16. The Lofts of North Main Street

The Lofts of North Main Street
St. Charles Historic District
9.6 out of 10, Exceptional, (183 reviews)
"Great place to stay. Our go to when visiting St.Charles or STL"
United States
jeramy p.
The price is AED 459
AED 956 total
includes taxes & fees
10 Aug - 11 Aug
The Lofts of North Main Street
Smart TV, fireplace, computer monitors

17. 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, (48 reviews)
"Great property, plenty of space, was very clean!"
United States
Will M.
The price is AED 707
AED 1,993 total
includes taxes & fees
10 Aug - 11 Aug
Charming open 4bd and screen-in porch! Sleeps 10!
Smart TV

18. 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 traveler
The price is AED 459
AED 956 total
includes taxes & fees
11 Aug - 12 Aug
Prime Loft of Main Street
Interior

19. 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, (53 reviews)
"This was our second stay, and like the first, everything was clean and comfortable. Homeowner was very responsive to some last minute questions that I had leading up to the trip which was much appreciated. Will definitely stay again in the future! "
United States
Rachel P.
The price is AED 533
AED 1,418 total
includes taxes & fees
17 Aug - 18 Aug
Spacious, 3 bedroom home, finished basement on quiet court
1 bedroom, WiFi (free)

20. 6649 2E | Boutique Hotel Studio in Forest Park

6649 2E | Boutique Hotel Studio in Forest Park
Dogtown
8.0 out of 10, Very Good, (16 reviews)
"Friendly staff helped with my booking, check in was easy. Would stay again! "
United States
Marie
The price is AED 257
AED 522 total
includes taxes & fees
10 Aug - 11 Aug
6649 2E | Boutique Hotel Studio in Forest Park
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

Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

10/10 Excellent
"Clean, comfortable, convenient, and the staff were great"
Barbara 1-night trip
Posted less than an hour ago
Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

Frequently asked questions

Can I find vacation rentals in Chesterfield?

Yes, we give you a choice of vacation rentals in Chesterfield near St. Louis Carousel, or you can go with a 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's the top vacation rental that Chesterfield has to offer?

Beautiful 4 bedroom Home by the Hill - Privacy Fenced Backyard and Fast Internet: Visitors like this Chesterfield vacation home rental. It has air-conditioning and laundry facilities 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 you can cook with friends or family.

How many vacation rentals are there in Chesterfield?

Choose from 7 Expedia vacation rentals in Chesterfield for a memorable vacation.

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 St. Louis Carousel and The Factory.

What are vacation rentals like in Chesterfield?

Vacation rentals are privately owned properties you can book for several days or more in Chesterfield. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for a family trip or a small group gathering.