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.
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.
The price is ￥17,367
￥116,877 total
includes taxes & fees
Jul 13 - Jul 14
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.
The price is ￥21,539
￥48,147 total
includes taxes & fees
Jul 7 - Jul 8
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, (18 reviews)
"We loved staying here, it was the perfect place for us to stay after the Blues game. "
United States
jessica s.
The price is ￥25,943
￥53,269 total
includes taxes & fees
Jul 19 - Jul 20
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.
The price is ￥18,554
￥40,227 total
includes taxes & fees
Jul 22 - Jul 23
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.
The price is ￥17,909
￥38,688 total
includes taxes & fees
Jul 13 - Jul 14
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.
The price is ￥12,907
￥28,805 total
includes taxes & fees
Jul 7 - Jul 8
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
The price is ￥13,230
￥30,797 total
includes taxes & fees
Jul 7 - Jul 8
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.
The price is ￥15,327
￥40,462 total
includes taxes & fees
Jul 13 - Jul 14
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.
The price is ￥15,973
￥37,496 total
includes taxes & fees
Jul 7 - Jul 8
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.
The price is ￥21,055
￥46,001 total
includes taxes & fees
Jul 13 - Jul 14
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
The price is ￥15,489
￥34,106 total
includes taxes & fees
Jul 14 - Jul 15
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.
The price is ￥19,361
￥37,333 total
includes taxes & fees
Jul 12 - Jul 13
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.
The price is ￥12,907
￥28,805 total
includes taxes & fees
Jul 7 - Jul 8
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.
The price is ￥14,554
￥31,577 total
includes taxes & fees
Jul 7 - Jul 8
Luxury stay with all you need within and around
Smart TV

Charming Loft Off Cherokee Pet Friendly & Free Parking

Charming 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.
The price is ￥12,262
￥23,941 total
includes taxes & fees
Aug 3 - Aug 4
Charming 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.
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.
The price is ￥48,241
￥95,651 total
includes taxes & fees
Jul 20 - Jul 21
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
The price is ￥26,427
￥52,490 total
includes taxes & fees
Jul 8 - Jul 9
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.
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

Drury Plaza Hotel St. Louis Union Station

Drury Plaza Hotel St. Louis Union Station

8/10 Good
"The room was comfortable. I wish there had been an exhaust fan in the bathroom. It was very humid after showers. The staff was friendly. Breakfast was very good, with many options both hot and cold. Parking was right behind the hotel, however I don't like having to pay the hotel to park in their parking garage. Overall, we had a nice stay."
Debra 1-night trip
Posted less than an hour ago
Drury Plaza Hotel St. Louis Union Station

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
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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 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.