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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Chesterfield vacation rentals

A spacious living area with a high ceiling, wooden beams, a fireplace, a dining area, and a cozy seating arrangement.

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

Private 3-Acre Retreat • Koi Pond & Waterfall
Wildwood
10.0 out of 10, Exceptional, (5 reviews)
"Absolutely stunning home! Beautiful, love the koy pond!"
United States
Bailey G.
$402 nightly
The price is $431
Oct 21 - Oct 22
Total with taxes and fees
Private 3-Acre Retreat • Koi Pond & Waterfall
A set of stone steps leading to a garage with a car parked inside.

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.
$138 nightly
The price is $147
Oct 8 - Oct 9
Total with taxes and fees
Studio, sleeps 5, short drive to Hidden Valley Ski Resort, parks &concert venues
A spacious living room with hardwood floors, a white armchair, a dark sofa, and a television on a stand.

3. Casa de Saint Charles

Casa de Saint Charles
Saint Charles
9.2 out of 10, Wonderful, (22 reviews)
"Everything was very nice and beautiful and perfectly set up for us will book again"
United States
Xavier H.
$331 nightly
The price is $348
Oct 11 - Oct 12
Total with taxes and fees
Casa de Saint Charles
A hotel room with a bed, a desk, a chair, a lamp, and a telephone.

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
$56 nightly
The price is $64
Oct 18 - Oct 19
Total with taxes and fees
1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
A living room with a sofa, coffee table, and patterned rug. There is a dining area with a bar and stools.

5. Private Entry Basement Suite • Pond & Farm View • Dog Friendly • St Peters

Private Entry Basement Suite • Pond & Farm View • Dog Friendly • St Peters
St. Peters
10.0 out of 10, Exceptional, (18 reviews)
"Excellent place to stay while visiting. Pet friendly a HUGE plus. The host was very pleasant to work with and the place really is thoughtfully outfitted. Would definitely stay here again"
United States
Chris B.
$260 nightly
The price is $290
Oct 14 - Oct 15
Total with taxes and fees
Private Entry Basement Suite • Pond & Farm View • Dog Friendly • St Peters
A cozy living room with a brick wall, a white sofa with colorful cushions, a small black table, and a potted plant.

6. 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
$211 nightly
The price is $226
Oct 8 - Oct 9
Total with taxes and fees
Prime Loft of Main Street
A spacious living area with a wooden floor, a dining table with chairs, a flat-screen TV mounted on the wall, and a kitchen area with modern appliances.

7. The Lofts of North Main Street

The Lofts of North Main Street
St. Charles Historic District
9.6 out of 10, Exceptional, (194 reviews)
"Very comfortable bed. Well stocked kitchen. Nice covered porch. Great neighborhood."
United States
Carla K.
$260 nightly
The price is $278
Oct 12 - Oct 13
Total with taxes and fees
The Lofts of North Main Street
A hallway with a wooden wall, a door leading to a bedroom, and a staircase.

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

St. Charles 1860's Gem - Sleeps 6!
St. Charles Historic District
9.8 out of 10, Exceptional, (166 reviews)
"Very nice very clean property. Very much enjoyed our stay"
United States
Joe R.
$251 nightly
The price is $268
Oct 11 - Oct 12
Total with taxes and fees
St. Charles 1860's Gem - Sleeps 6!
A row of multi-story buildings with commercial storefronts, including a cafe and a restaurant.

9. 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.
$184 nightly
The price is $203
Oct 12 - Oct 13
Total with taxes and fees
Historic Main Street Studio | Dog-Friendly
A hotel lobby with a staircase, a reception desk, and a chandelier.

10. 2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Westport
8.6 out of 10, Excellent, (47 reviews)
"Fantastic place!"
United States
Anonymous traveler
$56 nightly
The price is $64
Oct 18 - Oct 19
Total with taxes and fees
2 Queen Beds | Non-Smoking, Kitchen
A spacious foyer with a grand staircase, a piano, and a large rug.

11. White House at Grand Central

White House at Grand Central
3.5 star property
Grand Center
8.4 out of 10, Very good, (162 reviews)
"Nice find in the city"
United States
Mark
$134 nightly
The price is $151
Oct 11 - Oct 12
Total with taxes and fees
White House at Grand Central
A spacious living area with a dining table, sofa, and a large window with blinds.

12. Stunning Minimalist Gem | Fenced Backyard + W/D

Stunning Minimalist Gem | Fenced Backyard + W/D
Princeton Heights
9.8 out of 10, Exceptional, (29 reviews)
"Nice area, very well kept house and easy check-in process. Good parking"
United States
Christopher
Stunning Minimalist Gem | Fenced Backyard + W/D
A neatly made bed with a stack of folded towels, a bedside lamp, and a ceiling fan in a room with a large window and a wall-mounted artwork.

13. 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.
$244 nightly
The price is $269
Oct 12 - Oct 13
Total with taxes and fees
Walk to Main | Pet-Friendly Yard & Workspace
A hotel lobby with a staircase, a reception desk, and a seating area.

14. 2 Queen Beds | Mobil Access Tub Nsmk Kitchen

2 Queen Beds | Mobil Access Tub Nsmk Kitchen
Westport
9.8 out of 10, Exceptional, (45 reviews)
"Great place to stay!"
United States
Anonymous traveler
$56 nightly
The price is $64
Oct 25 - Oct 26
Total with taxes and fees
2 Queen Beds | Mobil Access Tub Nsmk Kitchen
A modern kitchen with white cabinets, a black refrigerator, and a central island.

15. Cottage on Main st- Low Cleaning Fee

Cottage on Main st- Low Cleaning Fee
St. Charles Historic District
10.0 out of 10, Exceptional, (12 reviews)
"Good location. Decorated very nicely. "
United States
Debbie A.
$272 nightly
The price is $291
Oct 26 - Oct 27
Total with taxes and fees
Cottage on Main st- Low Cleaning Fee
A modern apartment with a living room, kitchen, and dining area.

16. Adorable 2 King Bed Frenchtown Home

Adorable 2 King Bed Frenchtown Home
Saint Charles
10.0 out of 10, Exceptional, (5 reviews)
"Great location. Pet friendly. Perfect space for my wife and I to work remotely. So many great local places in close proximity. Host was quick to answer any and all questions. Would absolutely book again."
United States
Don S.
$360 nightly
The price is $403
Oct 20 - Oct 21
Total with taxes and fees
Adorable 2 King Bed Frenchtown Home
A modern kitchen with stainless steel appliances, white cabinetry, and a brick accent wall.

17. 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.
$313 nightly
The price is $345
Oct 12 - Oct 13
Total with taxes and fees
Historic Main St. Customs House Upstairs Apartment
A living room with a dark hardwood floor, a leather sofa, a ceiling fan, and a flat-screen TV mounted on the wall.

18. 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
$227 nightly
The price is $246
Oct 27 - Oct 28
Total with taxes and fees
Villa in Eureka 3.9 miles to Six Flags & 3.2 miles to Hidden Valley Ski Resort!
A living room with a white sofa, a black sofa, a glass coffee table, and a cityscape painting.

19. 6653 2S | Jewel of Central St. Louis

6653 2S | Jewel of Central St. Louis
Dogtown
8.0 out of 10, Very good, (26 reviews)
"It was clean and one of the best vrbo stays I went to."
United States
Sabria S.
$150 nightly
The price is $150
Oct 13 - Oct 14
Total with taxes and fees
6653 2S | Jewel of Central St. Louis
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

Pear Tree Inn St. Louis Near Union Station

Pear Tree Inn St. Louis Near Union Station

10/10 Excellent
"The employees at the Pear Tree are always so very nice and the room clean. The only annoying thing was the restaurant Sybergs was no longer there."
Darlene 3-night trip
Posted less than an hour ago
Pear Tree Inn St. Louis Near Union Station

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 $64 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 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.