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. 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
$67 nightly
The price is $78
Aug 10 - Aug 11
Total with taxes and fees
1 Queen Bed | Non-Smoking, Kitchen

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.
$101 nightly
The price is $107
Aug 9 - Aug 10
Total with taxes and fees
Chic 1- Queen Bed, Non Smoking-Near Airport, Kitchen, Twin Bed

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.
$273 nightly
The price is $300
Aug 9 - Aug 10
Total with taxes and fees
Spacious 2 Bedroom Townhome

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
$76 nightly
The price is $88
Aug 10 - Aug 11
Total with taxes and fees
2 Queen Beds | Non-Smoking, Kitchen

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
$71 nightly
The price is $83
Aug 10 - Aug 11
Total with taxes and fees
1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

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.
$228 nightly
The price is $244
Aug 9 - Aug 10
Total with taxes and fees
Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!

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
$76 nightly
The price is $88
Aug 10 - Aug 11
Total with taxes and fees
2 Queen Beds | Mobil Access Tub Nsmk Kitchen

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.
$242 nightly
The price is $266
Aug 10 - Aug 11
Total with taxes and fees
Walk to Main | Pet-Friendly Yard & Workspace

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.
$278 nightly
The price is $297
Aug 9 - Aug 10
Total with taxes and fees
Cottage on Main st- Low Cleaning Fee

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.
$206 nightly
The price is $227
Aug 9 - Aug 10
Total with taxes and fees
Historic Main Street Studio | Dog-Friendly

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.
$243 nightly
The price is $260
Aug 10 - Aug 11
Total with taxes and fees
Amazing Renovated Historic Loft on Main Street

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.
$307 nightly
The price is $338
Aug 12 - Aug 13
Total with taxes and fees
Historic Main St. Customs House Upstairs Apartment

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.
$260 nightly
The price is $278
Aug 9 - Aug 10
Total with taxes and fees
St. Charles 1860's Gem - Sleeps 6!

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.
$323 nightly
The price is $356
Aug 9 - Aug 10
Total with taxes and fees
Historic 1805 Main Street 2BR

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.
$261 nightly
The price is $298
Sep 6 - Sep 7
Total with taxes and fees
Great for Business Travelers! Comfortable Suite in St. Louis | BBQ Area

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.
$245 nightly
The price is $262
Aug 9 - Aug 10
Total with taxes and fees
The Lofts of North Main Street

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.
$480 nightly
The price is $543
Aug 10 - Aug 11
Total with taxes and fees
Charming open 4bd and screen-in porch! Sleeps 10!

18. Prime Loft of Main Street

Prime Loft of Main Street
St. Charles Historic District
9.8 out of 10, Exceptional, (115 reviews)
"Host was great. The cutest place in the perfect spot! "
United States
Anonymous traveler
$243 nightly
The price is $260
Aug 11 - Aug 12
Total with taxes and fees
Prime Loft of Main Street

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.
$333 nightly
The price is $386
Aug 19 - Aug 20
Total with taxes and fees
Spacious, 3 bedroom home, finished basement on quiet court

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
$142 nightly
The price is $142
Aug 10 - Aug 11
Total with taxes and fees
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

Find out more about Chesterfield

Everything you need to know about Chesterfield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chesterfield vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chesterfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $78 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield vacation 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 vacation.

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.

Explore a world of travel with Expedia

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.