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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Chesterfield vacation rentals

Interior

1. Private 3-Acre Retreat • Koi Pond & Waterfall

Private 3-Acre Retreat • Koi Pond & Waterfall
Wildwood
10.0 out of 10, Exceptional, (4 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 AED 786
AED 1,506 total
includes taxes & fees
21 Oct - 22 Oct
Private 3-Acre Retreat • Koi Pond & Waterfall
Property grounds

2. Studio, sleeps 5, short drive to Hidden Valley Ski Resort, parks &concert venues

Studio, sleeps 5, short drive to Hidden Valley Ski Resort, parks &concert venues
Ballwin
7.8 out of 10, Good, (24 reviews)
"Rooms were clean and everything we needed for our stay."
United States
Keith K.
The price is AED 275
AED 570 total
includes taxes & fees
22 Oct - 23 Oct
Studio, sleeps 5, short drive to Hidden Valley Ski Resort, parks &concert venues
Interior

3. 2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Westport
9.4 out of 10, Exceptional, (40 reviews)
"Fantastic place!"
United States
Anonymous traveler
The price is AED 208
AED 241 total
includes taxes & fees
27 Sep - 28 Sep
2 Queen Beds | Non-Smoking, Kitchen
1 bedroom, WiFi (free)

4. 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 traveler
The price is AED 208
AED 241 total
includes taxes & fees
27 Sep - 28 Sep
1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
Exterior

5. Historic Main Street Studio | Dog-Friendly

Historic Main Street Studio | Dog-Friendly
St. Charles Historic District
9.2 out of 10, Wonderful, (39 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 830 total
includes taxes & fees
27 Sep - 28 Sep
Historic Main Street Studio | Dog-Friendly
Smart TV, fireplace, computer monitors

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

Charming open 4bd and screen-in porch! Sleeps 10!
Saint Charles
8.8 out of 10, Excellent, (51 reviews)
"Great property, plenty of space, was very clean!"
United States
Will M.
The price is AED 711
AED 2,486 total
includes taxes & fees
27 Sep - 28 Sep
Charming open 4bd and screen-in porch! Sleeps 10!
Smart TV, stereo

7. 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 AED 459
AED 932 total
includes taxes & fees
27 Sep - 28 Sep
Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!
Interior

8. 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, (55 reviews)
"It was a perfect choice for our family to celebrate Christmas. "
United States
Leanne S.
The price is AED 452
AED 1,539 total
includes taxes & fees
27 Sep - 28 Sep
Spacious, 3 bedroom home, finished basement on quiet court
Coffee/tea maker, fridge, microwave, oven

9. Convenience 2 Bedroom House to Explore All of St Louis

Convenience 2 Bedroom House to Explore All of St Louis
University City
10.0 out of 10, Exceptional, (52 reviews)
"The house was immaculately clean and beds were extremely comfortable!"
United States
Anna M.
The price is AED 433
AED 981 total
includes taxes & fees
27 Sep - 28 Sep
Convenience 2 Bedroom House to Explore All of St Louis
Dining

10. 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 772
AED 1,019 total
includes taxes & fees
27 Sep - 28 Sep
Great for Business Travelers! Comfortable Suite in St. Louis | BBQ Area
Smart TV

11. 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
9.0 out of 10, Wonderful, (72 reviews)
"This was an extraordinary experience with great property and location and the description of the property was exact on. The host was very helpful when it came to anything we was needing very much appreciated and look forward to staying with this property owner again."
United States
Keith
The price is AED 507
AED 939 total
includes taxes & fees
6 Oct - 7 Oct
Villa in Eureka 3.9 miles to Six Flags & 3.2 miles to Hidden Valley Ski Resort!
1 bedroom, WiFi, bed sheets

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

Walk to Main | Pet-Friendly Yard & Workspace
St. Charles Historic District
10.0 out of 10, Exceptional, (12 reviews)
"Very close to downtown St. Charles and the Kati Trail. The home is cute and bed is comfortable. Easy check in process and fenced in back yard was nice to have."
United States
Jessica S.
The price is AED 496
AED 1,051 total
includes taxes & fees
27 Sep - 28 Sep
Walk to Main | Pet-Friendly Yard & Workspace
Smart TV

13. Prime Loft of Main Street

Prime Loft of Main Street
St. Charles Historic District
9.8 out of 10, Exceptional, (120 reviews)
"Host was great. The cutest place in the perfect spot! "
United States
Anonymous traveler
The price is AED 511
AED 1,018 total
includes taxes & fees
27 Sep - 28 Sep
Prime Loft of Main Street
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 496
AED 1,323 total
includes taxes & fees
24 Sep - 25 Sep
Historic 1805 Main Street 2BR
Interior

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

St. Charles 1860's Gem - Sleeps 6!
St. Charles Historic District
9.8 out of 10, Exceptional, (164 reviews)
"Very nice very clean property. Very much enjoyed our stay"
United States
Joe R.
The price is AED 479
AED 987 total
includes taxes & fees
27 Sep - 28 Sep
St. Charles 1860's Gem - Sleeps 6!
TV

16. 6655 1N | Elegance Near the St. Louis Arch

6655 1N | Elegance Near the St. Louis Arch
Dogtown
8.0 out of 10, Very good, (31 reviews)
"Great place to stay for the weekend. Cute and clean. Nice area with lot's of places in walking distance. I will definitely stay again."
United States
Brigitte B.
The price is AED 294
AED 551 total
includes taxes & fees
24 Sep - 25 Sep
6655 1N | Elegance Near the St. Louis Arch
Interior

17. The Lofts of North Main Street

The Lofts of North Main Street
St. Charles Historic District
9.6 out of 10, Exceptional, (191 reviews)
"Very comfortable bed. Well stocked kitchen. Nice covered porch. Great neighborhood."
United States
Carla K.
The price is AED 408
AED 893 total
includes taxes & fees
24 Sep - 25 Sep
The Lofts of North Main Street
Interior

18. 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 AED 511
AED 1,018 total
includes taxes & fees
27 Sep - 28 Sep
Amazing Renovated Historic Loft on Main Street
Interior

19. Chic Minimalist Gem w/ Fenced Backyard + W/D

Chic Minimalist Gem w/ Fenced Backyard + W/D
Princeton Heights
9.4 out of 10, Exceptional, (19 reviews)
"Very nice, clean, modern apartment in a safe, quiet, suburban neighborhood. We were very happy with our stay there for our visit to WashU and St. Louis."
United States
Dave
The price is AED 198
AED 659 total
includes taxes & fees
28 Sep - 29 Sep
Chic Minimalist Gem w/ Fenced Backyard + W/D
Coffee/tea maker, fridge, microwave, oven

20. 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 496
AED 1,323 total
includes taxes & fees
28 Sep - 29 Sep
Historic Main St. Customs House Upstairs Apartment
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

Hyatt Regency St. Louis at The Arch

Hyatt Regency St. Louis at The Arch

10/10 Excellent
"N/a"
Travis 5-night trip
Posted less than an hour ago
Hyatt Regency St. Louis at The Arch

Frequently asked questions

Can I find vacation rentals in Chesterfield?

Yes, we give you a choice of vacation rentals in Chesterfield near Sophia M. Sachs Butterfly House, 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?

Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!: Visitors like this Chesterfield vacation home rental. It is located in the city center and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Chesterfield?

Choose from 8 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 The Factory and St. Louis Premium Outlets.

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.