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

Chesterfield Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Chesterfield vacation rentals

1 bedroom, WiFi (free)

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 traveler
The price is ￥12,229
￥14,185 total
includes taxes & fees
Aug 24 - Aug 25
1 Queen Bed | Non-Smoking, Kitchen
Property grounds

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 ￥13,926
￥18,281 total
includes taxes & fees
Aug 1 - Aug 2
Chic 1- Queen Bed, Non Smoking-Near Airport, Kitchen, Twin Bed
Interior

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 ￥15,221
￥17,654 total
includes taxes & fees
Aug 3 - Aug 4
2 Queen Beds | Non-Smoking, Kitchen
1 bedroom, WiFi (free)

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 ￥14,407
￥16,711 total
includes taxes & fees
Aug 16 - Aug 17
1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
Smart TV, stereo

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 ￥21,298
￥42,938 total
includes taxes & fees
Jul 26 - Jul 27
Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!
1 bedroom, WiFi, bed sheets

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 ￥19,463
￥43,818 total
includes taxes & fees
Jul 27 - Jul 28
Duplex Hideaway in St. Charles, MO
TV, books

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 ￥21,380
￥46,009 total
includes taxes & fees
Jul 27 - Jul 28
St. Charles 1860's Gem - Sleeps 6!
Dining

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 ￥37,069
￥48,919 total
includes taxes & fees
Aug 2 - Aug 3
Great for Business Travelers! Comfortable Suite in St. Louis | BBQ Area
Interior

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 ￥20,495
￥42,792 total
includes taxes & fees
Aug 2 - Aug 3
The Lofts of North Main Street
Coffee/tea maker, fridge, microwave, oven

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 ￥22,772
￥47,673 total
includes taxes & fees
Aug 3 - Aug 4
Convenience 2 Bedroom House to Explore All of St Louis
Interior

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 ￥22,772
￥45,579 total
includes taxes & fees
Aug 5 - Aug 6
Amazing Renovated Historic Loft on Main Street
Studio Suite, 1 King Bed | Desk, laptop workspace, blackout drapes, WiFi (surcharge)

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 ￥62,624
￥86,066 total
includes taxes & fees
Jul 27 - Jul 28
Value Suites Extended Stay - St Louis
Smart TV

Prime Loft of Main Street

Prime Loft of Main Street
St. Charles Historic District
9.8 out of 10, Exceptional, (114 reviews)
"Host was great. The cutest place in the perfect spot! "
United States
Anonymous traveler
The price is ￥20,495
￥42,956 total
includes taxes & fees
Jul 26 - Jul 27
Prime Loft of Main Street
Coffee/tea maker, fridge, microwave, oven

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 ￥26,540
￥63,446 total
includes taxes & fees
Aug 2 - Aug 3
Historic Main St. Customs House Upstairs Apartment
Microwave, oven, stovetop, dishwasher

Stunning 1890's Home - Sleeps 8!

Stunning 1890's Home - Sleeps 8!
St. Charles Historic District
10.0 out of 10, Exceptional, (128 reviews)
"Super cute property, fantastic location. Very well maintained and clean, would definitely stay here again. "
United States
Jason T.
The price is ￥29,555
￥64,823 total
includes taxes & fees
Aug 24 - Aug 25
Stunning 1890's Home - Sleeps 8!
Interior

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, (51 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 ￥23,755
￥63,721 total
includes taxes & fees
Aug 2 - Aug 3
Spacious, 3 bedroom home, finished basement on quiet court
Coffee/tea maker, fridge, microwave, oven

The Original Custom House!

The Original Custom House!
St. Charles Historic District
9.6 out of 10, Exceptional, (40 reviews)
"The location is excellent. "
United States
McRay H.
The price is ￥26,540
￥63,446 total
includes taxes & fees
Jul 30 - Jul 31
The Original Custom House!
TV

6655 1N | Elegance Near the St. Louis Arch

6655 1N | Elegance Near the St. Louis Arch
Dogtown
7.8 out of 10, Good, (29 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 ￥13,106
￥24,574 total
includes taxes & fees
Jul 27 - Jul 28
6655 1N | Elegance Near the St. Louis Arch
1 bedroom, WiFi (free)

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 ￥11,468
￥23,264 total
includes taxes & fees
Aug 3 - Aug 4
6649 2E | Boutique Hotel Studio in Forest Park
Smart TV, fireplace, computer monitors

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)
"Great property, plenty of space, was very clean!"
United States
Will M.
The price is ￥33,520
￥91,496 total
includes taxes & fees
Jul 26 - Jul 27
Charming open 4bd and screen-in porch! Sleeps 10!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterfield Hotel Reviews

Drury Plaza Hotel St. Louis at the Arch

Drury Plaza Hotel St. Louis at the Arch

10/10 Excellent
"This is an amazing hotel right by the arch!"
Daniel 1-night trip
Posted less than an hour ago
Drury Plaza Hotel St. Louis at the Arch

Find out more about Chesterfield

Search for holiday rentals in Chesterfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesterfield using one of the methods below:

  • View our selection of featured holiday rentals in Chesterfield
  • Use the map to find apartments and other holiday homes in the Chesterfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesterfield while they last

Look no further and take a look at our great range of rental properties in Chesterfield!

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?

Pet-Friendly Soulard Townhouse · 2BR/2BA · Parking + Rooftop Deck: Visitors like this Chesterfield vacation home rental. It 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 the garden in this rental home to help you unwind.

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. While in the area, you can also visit popular places like Six Flags St. Louis and St. Louis Zoo.

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.