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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)
"Easy check-in, easy parking, cold ac, wonderful location. Would love to stay here again. "
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)
"Very cute condo it maximizes the space well, in addition the view is awesome! Highly recommend to anyone thinking of staying here"
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)
"Check in was easy, location was nice, clean, beds were comfy, and would definitely stay again!"
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)
"Close to so many must see things in St Louis"
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)
"Great condo and location . "
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)
"My stay was amazing. It was just enough space for and the area was pretty quiet despite being next to the highway. The host was very attentive to our needs as well."
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)
"In town for work but wanted to relax in the evening and this place was perfect for that thank you"
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)
"We had a great time staying here. The condo was clean and fully stocked and in a great location."
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)
"Everything was great!"
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)
"Location was perfect for our activities during our stay. And the host was super helpful."
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)
"We enjoyed our stay at the apartment. Location is handy, within walking distance to the park and public transportation. Clean, tidy and quiet."
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)
"Clean and nice place to stay, I’ll be coming back whenever I’m in town."
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)
"It was really nice being able to get away from the crowds and traffic and stay someplace quiet and peaceful. The condo was perfect and our 6 year old loved the bunk beds."
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)
"Our stay was very home-like, safe, and comfortable."
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)
"This property is within easy walking distance to ALL of historic downtown St Charles. It's obvious the owners take great care in keeping The Guest House in perfect condition, with every possible amenity provided. Very comfortable stay. We'll absolutely be back!"
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)
"This place is INCREDIBLE!!! We have little kids, a teenager, a senior and two adults in the family and EVERYONE absolutely LOVED it! We can't wait to go back! This will definitely be our go to spot when visiting St Louis. The host was extremely communicative. There was plenty of space for everyone. It is decorated incredibly, everyone got a kick out of it! "
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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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.