Vacation rentals in Chesterfield

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Chesterfield

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

Guest favourite
Home in St. Peters
Private Walkout w King Bed & Bath + large livingrm
Our house sits in a very quiet and safe neighborhood. When you stay with us you will enter through the walkout basement. You have full access to our very private downstairs apartment. This will enter you right into the very large living area. The master bedroom is complete with a King bed, black out curtains and walk-in closet. Attached is a full size bathroom with walk-in shower. Amenities include television, DVD, WiFi, Kuerig, mini-fridge and access to patio/porch with backyard fire pit.
Oct. 9 – 16
$116 CAD per night
4.88 out of 5 average rating, 304 reviews
Guest favourite
Tiny homes in Pacific
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!
Jan. 17 – 24
$158 CAD per night
4.96 out of 5 average rating, 156 reviews
Guest favourite
Home in Saint Charles
*HotTub* The Jewel on 5th-2br2b-near Historic Main
A true gem 15 mins from St Louis Lambert Airport-enjoy a well equipped, century home with a short walk to Historic Main and a HOTTUB. The large stocked kitchen is great for entertaining. Master bedrm w/luxurious, king sized, 4 poster bed and ensuite bathrm awaits you. In the private, queen suite you’ll find its own bathrm and another door leading onto the deck. The chair off the kitchen folds out to a standard twin and bedding is provided for the sofa as well. This charming jewel accommodates 6.
Oct. 27 – Nov. 3
$440 CAD per night
4.98 out of 5 average rating, 179 reviews

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 favourite
Home in Saint Charles
Bright & Cozy Shotgun 1 Block from Historic DT.
Oct. 14 – 21
$213 CAD per night
4.98 out of 5 average rating, 170 reviews
Guest favourite
Home in Maryland Heights
Cozy house to call home away from home ❤️🏡
Apr. 29 – May 6
$175 CAD per night
4.84 out of 5 average rating, 145 reviews
Guest favourite
Guest suite in Wildwood
Spacious suite,private patio,safe,horse property
Sep. 25 – Oct. 2
$209 CAD per night
4.83 out of 5 average rating, 139 reviews
Guest favourite
Bungalow in Saint Charles
Patio House, secluded in heartbeat of Main Street
Feb. 7 – 14
$177 CAD per night
4.99 out of 5 average rating, 161 reviews
Superhost
Tiny homes in Pacific
Route 66 Cozy Cottage
Feb. 21 – 28
$159 CAD per night
4.89 out of 5 average rating, 476 reviews
Guest favourite
Home in St. Louis
Cheerful and spacious 2 bedroom home with parking
Aug. 13 – 20
$185 CAD per night
4.88 out of 5 average rating, 199 reviews
Superhost
Bungalow in St. Louis
“HOT TUB” Oasis in the heart of the city!
Feb. 24 – Mar. 3
$250 CAD per night
4.81 out of 5 average rating, 426 reviews
Guest favourite
Home in St. Louis
Garden Cottage-Safe Private Parking!
Sep. 2 – 9
$206 CAD per night
4.98 out of 5 average rating, 503 reviews
Guest favourite
Cabin in St Charles
Camp Mill Pond: Historic Cabin Near Main Street
Sep. 5 – 10
$327 CAD per night
4.98 out of 5 average rating, 290 reviews
Guest favourite
Guest suite in St. Louis
Chic, Comfortable and Convenient
Dec. 8 – 15
$124 CAD per night
4.94 out of 5 average rating, 310 reviews
Guest favourite
Guesthouse in Maplewood
Weaver Guest House
Aug. 16 – 23
$168 CAD per night
4.98 out of 5 average rating, 359 reviews
Guest favourite
Loft in Washington
2nd Street Loft - Riverview
Oct. 21 – 28
$157 CAD per night
4.99 out of 5 average rating, 289 reviews

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

Destinations to explore