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

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, (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.
$362 nightly
The price is $388
Sep 28 - Sep 29
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 4 - Oct 5
Total with taxes and fees
Studio, sleeps 5, short drive to Hidden Valley Ski Resort, parks &concert venues
A hotel lobby with a staircase, a reception desk, and a chandelier.

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
$59 nightly
The price is $68
Oct 19 - Oct 20
Total with taxes and fees
2 Queen Beds | Non-Smoking, Kitchen
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
$59 nightly
The price is $68
Oct 19 - Oct 20
Total with taxes and fees
1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
A row of multi-story buildings with commercial storefronts, including a cafe and a restaurant.

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.
$204 nightly
The price is $225
Sep 24 - Sep 25
Total with taxes and fees
Historic Main Street Studio | Dog-Friendly
A spacious living area with a grey sofa, a wooden coffee table, and a kitchen area with a bar stool seating.

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.
$598 nightly
The price is $676
Sep 23 - Sep 24
Total with taxes and fees
Charming open 4bd and screen-in porch! Sleeps 10!
A living room with a sofa, armchairs, a coffee table, a lamp, a ceiling fan, and a rug.

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.
$237 nightly
The price is $254
Sep 27 - Sep 28
Total with taxes and fees
Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!
A spacious kitchen with white cabinets, a central island with bar stools, a stainless steel refrigerator, and a microwave.

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.
$362 nightly
The price is $419
Sep 27 - Sep 28
Total with taxes and fees
Spacious, 3 bedroom home, finished basement on quiet court
A compact kitchen with white cabinets, a stainless steel refrigerator, a coffee maker, and a hanging pendant light.

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.
$247 nightly
The price is $267
Sep 27 - Sep 28
Total with taxes and fees
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.
$244 nightly
The price is $278
Sep 27 - Sep 28
Total with taxes and fees
Great for Business Travelers! Comfortable Suite in St. Louis | BBQ Area
A living room with a dark hardwood floor, a leather sofa, a ceiling fan, and a flat-screen TV mounted on the wall.

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
$240 nightly
The price is $259
Sep 23 - Sep 24
Total with taxes and fees
Villa in Eureka 3.9 miles to Six Flags & 3.2 miles to Hidden Valley Ski Resort!
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.

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.
$260 nightly
The price is $286
Sep 27 - Sep 28
Total with taxes and fees
Walk to Main | Pet-Friendly Yard & Workspace
A cozy living room with a brick wall, a white sofa with colorful cushions, a small black table, and a potted plant.

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
$211 nightly
The price is $226
Sep 23 - Sep 24
Total with taxes and fees
Prime Loft of Main Street
A modern kitchen with white cabinetry, stainless steel appliances, and a dining area with a wooden table and chairs.

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.
$327 nightly
The price is $360
Sep 24 - Sep 25
Total with taxes and fees
Historic 1805 Main Street 2BR
A hallway with a wooden wall, a door leading to a bedroom, and a staircase.

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.
$265 nightly
The price is $284
Sep 27 - Sep 28
Total with taxes and fees
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.
$150 nightly
The price is $150
Sep 24 - Sep 25
Total with taxes and fees
6655 1N | Elegance Near the St. Louis Arch
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.

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.
$259 nightly
The price is $277
Sep 24 - Sep 25
Total with taxes and fees
The Lofts of North Main Street
A staircase with white railings and a ceiling fan.

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.
$259 nightly
The price is $277
Sep 27 - Sep 28
Total with taxes and fees
Amazing Renovated Historic Loft on Main Street
A modern kitchen with a built-in refrigerator, a dining area with a wooden table and benches, a gray sofa, and large windows providing natural light.

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
$153 nightly
The price is $180
Sep 28 - Sep 29
Total with taxes and fees
Chic Minimalist Gem w/ Fenced Backyard + W/D
A modern kitchen with stainless steel appliances, white cabinetry, and a brick accent wall.

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.
$327 nightly
The price is $360
Sep 28 - Sep 29
Total with taxes and fees
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

Drury Plaza Hotel St. Louis Union Station

Drury Plaza Hotel St. Louis Union Station

10/10 Excellent
"This hotel is a former 1900s YMCA, across a side street from the grand old Union RR station. Our king bed room was clean and cozy; bath was also, with great water pressure. We appreciated the complementary and substantial evening snacks and beverages. After a long day of driving and touring the Gateway Arch, it was pleasant just to enjoy the hotel. There was a nice pool and hot tub in the lower level, though we didn’t use them. Staff was very helpful, and parking was adjacent and easy to use."
D Arlyn M 1-night trip
Posted 2 hours ago
Drury Plaza Hotel St. Louis 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 $68 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.