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
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Chesterfield vacation rentals

Interior

3+ acres, fast wi-fi, garage parking, Koi pond

3+ acres, fast wi-fi, garage parking, Koi pond
Wildwood
10.0 out of 10, Exceptional, (1 review)
"Absolutely stunning home! Beautiful, love the koy pond!"
United States
Bailey G.
$493 nightly
The price is $529
Jul 14 - Jul 15
Total with taxes and fees
3+ acres, fast wi-fi, garage parking, Koi pond
Children's area

2BDRM Downtown Cozy Getaway | Marcel Stays

2BDRM Downtown Cozy Getaway | Marcel Stays
Downtown St. Louis
9.2 out of 10, Wonderful, (30 reviews)
"The place was clean, and the owner/manager was very responsive to questions/issues we had during the stay"
United States
Amy B.
$727 nightly
The price is $730
Jul 13 - Jul 14
Total with taxes and fees
2BDRM Downtown Cozy Getaway | Marcel Stays
Interior

Soulard 4BR Near Busch & Arch — Private Patio, Fast Wi-Fi, Easy Parking

Soulard 4BR Near Busch & Arch — Private Patio, Fast Wi-Fi, Easy Parking
Soulard
9.2 out of 10, Wonderful, (13 reviews)
"Great all around experience. "
United States
jessica s.
$287 nightly
The price is $310
Jul 15 - Jul 16
Total with taxes and fees
Soulard 4BR Near Busch & Arch — Private Patio, Fast Wi-Fi, Easy Parking
Fridge, microwave, oven, stovetop

Spacious 4BR Soulard Retreat • Patio Games, Balcony, Family-Friendly Near Busch

Spacious 4BR Soulard Retreat • Patio Games, Balcony, Family-Friendly Near Busch
Soulard
8.0 out of 10, Very Good, (19 reviews)
"We loved staying here, it was the perfect place for us to stay after the Blues game. "
United States
jessica s.
$286 nightly
The price is $309
Jul 13 - Jul 14
Total with taxes and fees
Spacious 4BR Soulard Retreat • Patio Games, Balcony, Family-Friendly Near Busch
Interior

Soulard Gem Dual Master 2BR w/ own EnSuites & Deck

Soulard Gem Dual Master 2BR w/ own EnSuites & Deck
Soulard
9.8 out of 10, Exceptional, (55 reviews)
"Loved the place! Comfortable beds, safe neighborhood, excellent host!"
United States
lora P.
$226 nightly
The price is $250
Jul 22 - Jul 23
Total with taxes and fees
Soulard Gem Dual Master 2BR w/ own EnSuites & Deck
Smart TV, offices

Classic Soulard 2BD King Master & Private Deck

Classic Soulard 2BD King Master & Private Deck
Soulard
9.8 out of 10, Exceptional, (59 reviews)
"We had a great time. Thank you."
United States
Dominic R.
$202 nightly
The price is $218
Jul 22 - Jul 23
Total with taxes and fees
Classic Soulard 2BD King Master & Private Deck
1 bedroom, desk, iron/ironing board, travel crib

Soulard King 1BR - Personal Gym and Sauna Oasis

Soulard King 1BR - Personal Gym and Sauna Oasis
Soulard
10.0 out of 10, Exceptional, (12 reviews)
"Fantastic place. "
United States
Andrew W.
$167 nightly
The price is $181
Aug 4 - Aug 5
Total with taxes and fees
Soulard King 1BR - Personal Gym and Sauna Oasis
Interior

Cozy Soulard 2BR w/ Free Parking

Cozy Soulard 2BR w/ Free Parking
Soulard
9.6 out of 10, Exceptional, (65 reviews)
"This is a gem in the heart of a historic neighborhood with the best bars and restaurants and music in the city! Could not pick a better location. It was so cute with a great view and wonderful hosts!!!"
United States
Renee
$216 nightly
The price is $235
Jul 20 - Jul 21
Total with taxes and fees
Cozy Soulard 2BR w/ Free Parking
Smart TV, fireplace

Cozy Soulard Getaway

Cozy Soulard Getaway
Soulard
9.2 out of 10, Wonderful, (44 reviews)
"Good stay. Great location "
United States
Sean D.
$233 nightly
The price is $255
Jul 13 - Jul 14
Total with taxes and fees
Cozy Soulard Getaway
Fridge, microwave, oven, stovetop

Top of Geyer apartment

Top of Geyer apartment
Soulard
9.6 out of 10, Exceptional, (53 reviews)
"This was a great stay. The space, decor, and location was perfect. "
United States
Jerry S.
$217 nightly
The price is $237
Jul 13 - Jul 14
Total with taxes and fees
Top of Geyer apartment
Exterior

Brand New! Soulard Charmer - Pet Friendly.

Brand New! Soulard Charmer - Pet Friendly.
Soulard
9.6 out of 10, Exceptional, (41 reviews)
"Great location with lots of space and amenities"
United States
Anne M.
$263 nightly
The price is $287
Jul 13 - Jul 14
Total with taxes and fees
Brand New! Soulard Charmer - Pet Friendly.
TV, fireplace, offices

Historic Soulard 2-BR Flat | Balcony, Workspace, Parking – Walk to Market

Historic Soulard 2-BR Flat | Balcony, Workspace, Parking – Walk to Market
Soulard
8.8 out of 10, Excellent, (18 reviews)
"We had a great experience. The place was clean and had a lot of character. The check in and check out process was easy. Dan had great communication with me. We walked to Miami Cafe around the corner and recommend it to anyone who stays here. The atmosphere and neighborhood had a lot of character. We enjoyed our stay!"
United States
Cheryl
$182 nightly
The price is $197
Jul 14 - Jul 15
Total with taxes and fees
Historic Soulard 2-BR Flat | Balcony, Workspace, Parking – Walk to Market
Fridge, microwave, oven, stovetop

House in Soulard near Busch Stadium, Ballpark Village and Anheuser Busch Brewery

House in Soulard near Busch Stadium, Ballpark Village and Anheuser Busch Brewery
Soulard
10.0 out of 10, Exceptional, (114 reviews)
"The house just has a good vibe and I love how close it is to the city."
United States
Sammie K.
$212 nightly
The price is $230
Jul 15 - Jul 16
Total with taxes and fees
House in Soulard near Busch Stadium, Ballpark Village and Anheuser Busch Brewery
Fridge, microwave, oven, coffee/tea maker

Stylish South City King 1BR Apt

Stylish South City King 1BR Apt
Marine Villa
10.0 out of 10, Exceptional, (9 reviews)
"Beatiful home close to venues and shops. "
United States
Kelly H.
$165 nightly
The price is $179
Jul 13 - Jul 14
Total with taxes and fees
Stylish South City King 1BR Apt
Smart TV

Luxury stay with all you need within and around

Luxury stay with all you need within and around
Fox Park
8.8 out of 10, Excellent, (16 reviews)
"Convenient street parking, convenient location, clean, good communication throughout stay"
United States
Kala K.
$183 nightly
The price is $199
Jul 12 - Jul 13
Total with taxes and fees
Luxury stay with all you need within and around
Smart TV

Little Loft Off Cherokee Pet Friendly & Free Parking

Little Loft Off Cherokee Pet Friendly & Free Parking
Benton Park West
9.6 out of 10, Exceptional, (70 reviews)
"We love staying here!"
United States
Jennifer V.
$136 nightly
The price is $148
Aug 3 - Aug 4
Total with taxes and fees
Little Loft Off Cherokee Pet Friendly & Free Parking
Fridge, microwave, oven, stovetop

Stunning & Luxurious 4-story house. 5BDR. Rooftop Deck w/ views of the Arch!

Stunning & Luxurious 4-story house. 5BDR. Rooftop Deck w/ views of the Arch!
The Gate
9.8 out of 10, Exceptional, (119 reviews)
"We had a great stay. Incredible rooftop views."
United States
Jenn O.
$672 nightly
The price is $729
Jul 28 - Jul 29
Total with taxes and fees
Stunning & Luxurious 4-story house. 5BDR. Rooftop Deck w/ views of the Arch!
Fridge, microwave, oven, stovetop

Modern & Luxurious. 4BR. Sleep 12. Minutes to downtown

Modern & Luxurious. 4BR. Sleep 12. Minutes to downtown
The Gate
9.8 out of 10, Exceptional, (46 reviews)
"Parking was great, it was a good trip!"
United States
Kali K.
$549 nightly
The price is $596
Jul 20 - Jul 21
Total with taxes and fees
Modern & Luxurious. 4BR. Sleep 12. Minutes to downtown
Fridge, microwave, oven, stovetop

Entire 4BR Home near Lafayette Square

Entire 4BR Home near Lafayette Square
The Gate
9.8 out of 10, Exceptional, (105 reviews)
"Wonderful home in a great location that is convenient to everything!"
United States
Anonymous traveler
Entire 4BR Home near Lafayette Square
Interior

NEW Modern & Luxe 5BDR House. Sleep 14. Downtown 5min away

NEW Modern & Luxe 5BDR House. Sleep 14. Downtown 5min away
The Gate
9.6 out of 10, Exceptional, (42 reviews)
"Great stay!"
United States
MaryAnn V.
$656 nightly
The price is $714
Jul 22 - Jul 23
Total with taxes and fees
NEW Modern & Luxe 5BDR House. Sleep 14. Downtown 5min away
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 Airport

Pear Tree Inn St. Louis Airport

10/10 Excellent
"The staff were all great. Very friendly and helpful. We were not able to make happy hour, but that is a very nice touch. The room was large and clean. Breakfast was good. Lots of options."
Mark 1-night trip
Posted 2 hours ago
Pear Tree Inn St. Louis Airport

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 $100 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?

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 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 Sophia M. Sachs Butterfly House and Missouri River 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.