Vacation rentals in Chesterfield

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Top-rated vacation rentals in Chesterfield

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Tiny home in Pacific

4.96 out of 5 average rating, 156 reviews

Route 66 railroad shanty, a cozy artsy small space

This 536 s.f. house, believed to have once been a sleeping shanty for railroad crews switching shifts for the night. Fully renovated and updated in 2021 by a local artist, you will find custom metal art throughout, granite countertops and a very warm cabin feel featuring a kitchen and bathroom finished with locally sourced Missouri dark red cedar, 10 minutes from six flags, Purina farms 15 min from hidden valley and 45 min from downtown this place is in a great location and will not disappoint!

Jul 9 – 16

G$23,454 GYD per night
Guest favorite

Home in Saint Charles

4.98 out of 5 average rating, 483 reviews

301 Guesthouse SuperHost/Shop Discounts/Katy Trail

Our 301 Guest House is new and completely remodeled in 2018! It’s ideal for one or two people with beautiful furnishings, great queen bed, lots of amenities, full kitchen, with big back yard and patio to enjoy outdoors too! Cable and FAST WiFi! Enjoy light Breakfast! BEST location, Great events year round within walking distance, with being only about 2 blocks from S. Main St, where there are about 100 gift shops n restaurants! Katy Trail is so close, with Spring, Summer, Fall and Xmas events!

Nov 6 – 13

G$27,994 GYD per night
Guest favorite

Guest suite in Saint Charles

4.95 out of 5 average rating, 292 reviews

Creekside Suite - Peaceful, Spacious, and Comfy

Enjoy your stay in a spacious walkout basement-level suite that includes bedroom, bathroom, living/dining room & patio. Bedroom has queen bed, dresser, desk & TV. Living room has futon, books, games & TV. TVs have Netflix. Suite has minifridge, microwave, toaster & coffee-maker. Eat at the dining table or sit up to the window counter to look out on the creek & woodlands behind the house. Situated in a quiet, safe neighborhood with parks & ponds. Just 8 miles from historic downtown St Charles.

Apr 2 – 9

G$23,321 GYD per night

Popular amenities for Chesterfield vacation rentals

Stay near Chesterfield's top sights

St. Louis Premium Outlets33 locals recommend
Topgolf27 locals recommend
Chesterfield Mall10 locals recommend
The Butterfly House54 locals recommend
The Cheesecake Factory3 locals recommend
St. Luke's Hospital4 locals recommend

Other great vacation rentals in Chesterfield

Guest favorite

Home in Saint Charles

4.88 out of 5 average rating, 538 reviews

The Benton House - With fenced yard!

Mar 15 – 22

G$27,769 GYD per night
Guest favorite

Home in St. Louis

4.98 out of 5 average rating, 506 reviews

Garden Cottage-Safe Private Parking!

Sep 11 – 18

G$26,644 GYD per night
Superhost

Tiny home in Pacific

4.89 out of 5 average rating, 479 reviews

Route 66 Cozy Cottage

Nov 8 – 15

G$22,770 GYD per night
Guest favorite

Bungalow in St. Louis

4.99 out of 5 average rating, 285 reviews

Darling Bungalow! King Bed!

May 28 – Jun 4

G$22,952 GYD per night
Guest favorite

Home in Ballwin

4.94 out of 5 average rating, 134 reviews

Entire lower level of our home w/Paris Theme

Sep 8 – 15

G$21,081 GYD per night
Guest favorite

Home in Belleville

4.99 out of 5 average rating, 142 reviews

The Pool House 1-Bedroom Home with Hot Tub & Pool

May 26 – Jun 2

G$24,448 GYD per night
Guest favorite

Cottage in Eureka

4.92 out of 5 average rating, 234 reviews

Beautiful Cottage on Large Private Lot

Oct 19 – 26

G$29,675 GYD per night
Superhost

Bungalow in St. Louis

4.81 out of 5 average rating, 427 reviews

“HOT TUB” Oasis in the heart of the city!

Jan 27 – Feb 3

G$31,807 GYD per night
Guest favorite

Guest suite in Wildwood

4.83 out of 5 average rating, 139 reviews

Spacious suite,private patio,safe,horse property

Nov 9 – 16

G$28,637 GYD per night
Guest favorite

Loft in Washington

4.99 out of 5 average rating, 290 reviews

2nd Street Loft - Riverview

Sep 18 – 25

G$20,985 GYD per night
Guest favorite

Guest suite in St. Louis

4.94 out of 5 average rating, 313 reviews

Chic, Comfortable and Convenient

Aug 16 – 23

G$18,840 GYD per night
Guest favorite

Home in Kirkwood

4.98 out of 5 average rating, 171 reviews

A Kirkwood Cottage, Quaint Suburb of St Louis

Oct 2 – 9

G$33,008 GYD per night

Quick stats about vacation rentals in Chesterfield

Total rentals

30 properties

Wifi availability

20 properties include access to wifi

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

150 reviews

Frequently Asked Questions

  • Do house rentals in Chesterfield have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in Chesterfield. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Chesterfield?

    Four-legged friends are welcome in Chesterfield. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Do house rentals in Chesterfield have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Chesterfield. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Chesterfield have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Chesterfield. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Chesterfield?

    Chesterfield has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for House Rentals in Chesterfield?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with air conditioning, over 10 homes with wifi, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Chesterfield have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Chesterfield. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in Chesterfield?

    Yes! Work meets play with ease at over 10 vacation rentals in Chesterfield featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore