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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Compare 99 Condo Rentals in Chesterfield with updated reviews, rates, and availability.

Family + Pet Friendly, King & Queen beds, steps to Metrolink+ Free Gated Parking
Fridge, microwave, oven, stovetop

Family + Pet Friendly, King & Queen beds, steps to Metrolink+ Free Gated Parking

9.8 out of 10, Exceptional, (34)
"This apartment was fantastic! It’s in a neat old brick building, really clean and great communication before and during the visit. Very quiet at night. Beds were very comfortable. Location is perfect: literally around the corner from the metro stop that takes you to the airport or downtown and walk another block you’ll be in Forest Park. We went to the Gateway Arch and it was easy, so nice not to have to deal with driving and finding parking downtown. Highly recommend this place! "
Family + Pet Friendly, King & Queen beds, steps to Metrolink+ Free Gated Parking
Lionshead Lake Retreat
4 bedrooms, iron/ironing board, free WiFi, bed sheets

Lionshead Lake Retreat

Lionshead Lake Retreat
Lakefront Studio Condo
Bar (on property)

Lakefront Studio Condo

2.0 star property
9.4 out of 10, Exceptional, (11)
"We were there for a wedding at the The Aspen Center.It so nice not to drive home. Plus it was so nice and comfortable. Couldn’t ask for anything more!"
The price is $255
includes taxes & fees
$245 per night
May 4 - May 5
Lakefront Studio Condo
Cozy & charming updated 2bdrm condo mins away from restaurants & entertainment!
Exterior detail

Cozy & charming updated 2bdrm condo mins away from restaurants & entertainment!

9.2 out of 10, Wonderful, (7)
"We loved the property and the neighborhood!"
Cozy & charming updated 2bdrm condo mins away from restaurants & entertainment!
1st Fl King+Queen Beds, pet friendly, Steps to Metrolink, Free Gated parking
Smart TV

1st Fl King+Queen Beds, pet friendly, Steps to Metrolink, Free Gated parking

9.4 out of 10, Exceptional, (30)
"My husband & kids stayed at this property for a spring break trip. It is a great location, just as described, older building which gives it character & good space for a family of four. The only negative thing I can say is that the living room furniture (couch, chair) are old & need to be replaced. They were both really uncomfortable. The listing said gated parking & we wanted that for safety but the gate wouldn’t ever close so it stayed open all day & night. Overall, we enjoyed our stay. It is a...
1st Fl King+Queen Beds, pet friendly, Steps to Metrolink, Free Gated parking
Gorgeous, Completely Remodeled, Waterfront Condo on Aspen Lake!
Beach nearby

Gorgeous, Completely Remodeled, Waterfront Condo on Aspen Lake!

10.0 out of 10, Exceptional, (29)
"I wasn’t too keen on staying so far from downtown St. Louis at first, but it turned out to be the best decision ever! The view was stunning, the place was incredible, and the host was super cool. The boys outside of not being able to play their game had a blast. We went for a walk on the trails, tried our luck at fishing, and almost went kayaking, haha! We had an amazing time and will definitely be back when the weather warms up again!!!!"
Gorgeous, Completely Remodeled, Waterfront Condo on Aspen Lake!
Welcome to comfort! Private condo near local sports and entertainment venues.
Fridge, microwave, oven, stovetop

Welcome to comfort! Private condo near local sports and entertainment venues.

8.0 out of 10, Very Good, (10)
"No surprises--exactly as how is pictured/described and what I expected for the price. Host was readily available and communicative; perfect place for what it is."
Welcome to comfort! Private condo near local sports and entertainment venues.
Lionshead Overlook Pt. II by Innsbrook Vacations!
Bar (on property)

Lionshead Overlook Pt. II by Innsbrook Vacations!

9.8 out of 10, Exceptional, (15)
"Excellent golf weekend location. Condo was perfect for our group of 5. Clean and plenty of space. Away from it all but easy access to restaurants and golf. Great view of the lake. Great communication with owner. "
The price is $565
includes taxes & fees
$546 per night
May 22 - May 23
Lionshead Overlook Pt. II by Innsbrook Vacations!
The Geneva Villa by Innsbrook Vacations!
Bar (on property)

The Geneva Villa by Innsbrook Vacations!

10.0 out of 10, Exceptional, (4)
"Comfortable and cozy for a long weekend stay!"
The Geneva Villa by Innsbrook Vacations!
The Geneva Studio by Innsbrook Vacations!
Bar (on property)

The Geneva Studio by Innsbrook Vacations!

10.0 out of 10, Exceptional, (1)
"The property is well kept and clean. The condo was clean and well furnished. "
The Geneva Studio by Innsbrook Vacations!
THIS IS THE ONE! Beautiful 2-BR 1.5 BA condo at PRIME downtown St. Louis!
Fridge, microwave, oven, stovetop

THIS IS THE ONE! Beautiful 2-BR 1.5 BA condo at PRIME downtown St. Louis!

10.0 out of 10, Exceptional, (1)
"The home has a great location in the city and the provided parking is real nice to have. The home was very clean and modern but still had a cozy feel. We had fun playing some of the games and relaxing watching the tv. The stay was great and the host was real responsive."
THIS IS THE ONE! Beautiful 2-BR 1.5 BA condo at PRIME downtown St. Louis!
The Hill
Fridge, microwave, oven, stovetop

The Hill

3.5 star property
10.0 out of 10, Exceptional, (1)
"Really cute and fun for a quick weekend getaway to St. L. Kids really enjoyed it, thank you! "
The Hill
The Great Room - fully cozy & private Townhome
Exterior

The Great Room - fully cozy & private Townhome

10.0 out of 10, Exceptional, (1)
"The place was beautiful and decorated well. Our experience was great and i recommend this rental. Would be nice if they honored military discount as I am a veteran. "
The Great Room - fully cozy & private Townhome
Studio Condo on the Water @ Innsbrook
Bar (on property)

Studio Condo on the Water @ Innsbrook

10.0 out of 10, Exceptional, (11)
"Clean, nice view, everything we needed was at the property "
The price is $345
includes taxes & fees
$328 per night
May 1 - May 2
Studio Condo on the Water @ Innsbrook
Lake Aspen Overlook by Innsbrook Vacations!
Bar (on property)

Lake Aspen Overlook by Innsbrook Vacations!

9.6 out of 10, Exceptional, (18)
"Nice property "
Lake Aspen Overlook by Innsbrook Vacations!
Business-Traveler Friendly 2-bedroom condo in fantastic Lake Saint Louis
Fridge, microwave, oven, stovetop

Business-Traveler Friendly 2-bedroom condo in fantastic Lake Saint Louis

2.0 star property
10.0 out of 10, Exceptional, (2)
"Convenient and clean."
Business-Traveler Friendly 2-bedroom condo in fantastic Lake Saint Louis
Spacious | Quiet | 1 bedroom duplex w free parking!
Fridge, microwave, oven, stovetop

Spacious | Quiet | 1 bedroom duplex w free parking!

10.0 out of 10, Exceptional, (22)
"The stay here was nice and comfortable. The neighbors were quiet. Conveniently located to our office in Maplewood."
Spacious | Quiet | 1 bedroom duplex w free parking!
Popular King + Queen Beds-Steps to Metrolink & Free Gated Parking
Exterior

Popular King + Queen Beds-Steps to Metrolink & Free Gated Parking

9.6 out of 10, Exceptional, (30)
"The apartment worked well for our family, was clean, and adequately stocked with supplies. Unfortunately, there was a lot of rain during our stay, so walking to the Delmar loop wasn't an option, and there weren't many restaurants or places to shop less than a mile away. Also, it was too early in the season for the trolley. The Metrolink was close-by, so we were able to get downtown easily."
Popular King + Queen Beds-Steps to Metrolink & Free Gated Parking
The Harris Overlook by Innsbrook Vacations!
Bar (on property)

The Harris Overlook by Innsbrook Vacations!

9.6 out of 10, Exceptional, (16)
"Innsbrook is a great place to stay if you have kids. There are deer everywhere. A great playground. A beach with shells to gather. Nature trails to hike. A market with wine/beer, ice cream and coffee among other things. The condo was clean and the listing was accurate. The only critique are the beds were not very comfortable. Our 3 year old even complained of back pain after sleeping on the pullout love seat. Other than that it’s a perfect spot for a weekend getaway! "
The price is $282
includes taxes & fees
$274 per night
May 19 - May 20
The Harris Overlook by Innsbrook Vacations!
Aspen Hideout by Innsbrook Vacations!
Bar (on property)

Aspen Hideout by Innsbrook Vacations!

9.2 out of 10, Wonderful, (7)
"very quiet as soon as we drove up deer and wildlife was everywhere very beauitful scenery. Also as we got to the place we were staying at as soon as we opened the patio door there were deer and other wildlife. The only thing me an my daughter didn't enjoy was the restaurant that was on the property called "The ClubHouse Bar And Grille" they were very rude I had made reservations. As soon as we got there and said we had reservations the woman at the front said they didn't take reservations. It...
Aspen Hideout by Innsbrook Vacations!
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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Other property types in Chesterfield

White House at Grand Central
Comfort Apartment | Individually decorated, individually furnished, desk, laptop workspace

White House at Grand Central

4.0 star property
8.6 out of 10, Excellent, (104)
"Did not like the smell of pot with in the building. Location was great to have easy access to many area activities."
The price is $172
includes taxes & fees
$147 per night
May 5 - May 6
White House at Grand Central
1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!
Outdoor dining

1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!

10.0 out of 10, Exceptional, (200)
"We are delighted to have found this beautiful VRBO and the quaint area of St. Charles! We were coming to St Louis to see our Phillies play the Cardinals but didn’t want to stay in the city. This was a PERFECT spot. Close enough to go exploring the city, but then coming back to the quiet historic streets of St Charles. The Guest House was cozy and unique with a peaceful view of the Missouri River just a golf stroke away. Steeped in history but certainly not lacking any modern amenities needed....
1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!
Funky mini loft in fox park! Pet friendly!!
Private kitchen

Funky mini loft in fox park! Pet friendly!!

7.8 out of 10, Good, (56)
"St. Louis overall wasn’t a vibe, the house inside was pretty cool. I wish the description showed the outside of the house and the location. It was very sketchy but thankfully nothing bad happened lol. My kids enjoyed all the Nicolas Cage stuff inside. Although we won’t be returning it was definitely decent for the price we paid. "
The price is $156
includes taxes & fees
$145 per night
May 7 - May 8
Funky mini loft in fox park! Pet friendly!!
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.

Frequently asked questions

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With Expedia, it’s a cinch to find your dream condo in Chesterfield. After a luxury stay? Make the most of our filters to search for properties that are 5-star rated. If you have a set budget, select how much you want to spend and then browse our fabulous deals. We’ll help you find a suitable stay whatever your vacation looks like.
How can I find cheap condos in Chesterfield?
With Expedia’s user-friendly filter tool, scoring cheap condos in Chesterfield couldn’t be simpler. To find accommodations that are very pocket friendly, tailor your search results by amenities, star rating and budget.
What is there to do in Chesterfield near my condo?
Chesterfield has enough activities and sights to entertain you for weeks, starting with St. Louis Premium Outlets. The Factory, Chesterfield Sports Fusion and Westfield Chesterfield Mall are other terrific attractions. If you have more time, Babler State Park and Sophia M. Sachs Butterfly House are nice finishing touches to your itinerary.