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

Chesterfield Vacation Rentals

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Our top choices for Chesterfield vacation rentals

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 CA $270
CA $541 total
includes taxes & fees
Sep 28 - Sep 29
Private 3-Acre Retreat • Koi Pond & Waterfall

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 CA $95
CA $207 total
includes taxes & fees
Oct 4 - Oct 5
Studio, sleeps 5, short drive to Hidden Valley Ski Resort, parks &concert venues

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 traveller
The price is CA $79
CA $92 total
includes taxes & fees
Oct 6 - Oct 7
2 Queen Beds | Non-Smoking, Kitchen

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 traveller
The price is CA $79
CA $92 total
includes taxes & fees
Oct 6 - Oct 7
1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

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 CA $144
CA $316 total
includes taxes & fees
Sep 24 - Sep 25
Historic Main Street Studio | Dog-Friendly

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 CA $270
CA $948 total
includes taxes & fees
Sep 23 - Sep 24
Charming open 4bd and screen-in porch! Sleeps 10!

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 CA $175
CA $357 total
includes taxes & fees
Sep 27 - Sep 28
Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!

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 CA $173
CA $585 total
includes taxes & fees
Sep 27 - Sep 28
Spacious, 3 bedroom home, finished basement on quiet court

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 CA $166
CA $373 total
includes taxes & fees
Sep 27 - Sep 28
Convenience 2 Bedroom House to Explore All of St Louis

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 CA $295
CA $387 total
includes taxes & fees
Sep 27 - Sep 28
Great for Business Travelers! Comfortable Suite in St. Louis | BBQ Area

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 CA $191
CA $363 total
includes taxes & fees
Sep 23 - Sep 24
Villa in Eureka 3.9 miles to Six Flags & 3.2 miles to Hidden Valley Ski Resort!

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 CA $189
CA $403 total
includes taxes & fees
Sep 27 - Sep 28
Walk to Main | Pet-Friendly Yard & Workspace

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 traveller
The price is CA $137
CA $317 total
includes taxes & fees
Sep 23 - Sep 24
Prime Loft of Main Street

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 CA $189
CA $504 total
includes taxes & fees
Sep 27 - Sep 28
Historic 1805 Main Street 2BR

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 CA $183
CA $393 total
includes taxes & fees
Sep 27 - Sep 28
St. Charles 1860's Gem - Sleeps 6!

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 CA $112
CA $210 total
includes taxes & fees
Sep 24 - Sep 25
6655 1N | Elegance Near the St. Louis Arch

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 CA $195
CA $390 total
includes taxes & fees
Sep 24 - Sep 25
The Lofts of North Main Street

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 CA $195
CA $390 total
includes taxes & fees
Sep 27 - Sep 28
Amazing Renovated Historic Loft on Main Street

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 CA $76
CA $252 total
includes taxes & fees
Sep 28 - Sep 29
Chic Minimalist Gem w/ Fenced Backyard + W/D

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 CA $189
CA $508 total
includes taxes & fees
Sep 28 - Sep 29
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

Find out more about Chesterfield

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chesterfield. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.