
House vacation rentals in Chesterfield
Find and book unique houses on Airbnb
Top-rated house rentals in Chesterfield
Guests agree: these houses are highly rated for location, cleanliness, and more.

Sunny South City Guest House
Newly-rehabbed & cozy guest house. Everything you need is located here in the historic Bevo Mill neighborhood. In the heart of south St. Louis city, you’re steps away from local businesses, including the picturesque, historical Das Bevo. Step into a vintage-styled oasis, featuring large windows with plenty of natural light, tall vaulted ceilings, comfy queen bed, unique fridge, breakfast bar, sizable bathroom with a large walk-in shower. Hang outside at the picnic table under cute string lights.

Pet & Child Friendly*Great Location*Ideal 4 Groups
Stay Awhile is more than a place to stay—it’s a memory maker! This spacious St. Louis vacation rental is tucked in a fantastic neighborhood & less than 30 minutes from top St. Louis attractions-like the Zoo & Arch! Designed for families, groups & pets, it offers cozy beds, a well-stocked kitchen & plenty of space for everyone. A one-of-a-kind Eye Spy game is hidden throughout the décor, making the home part of the adventure. Perfect for those who love comfort, convenience & a touch of whimsy.

Pacific Palace, super unique!
The Pacific Palace is unlike any other Airbnb! Located in the heart of downtown Pacific, Missouri - only 2 minutes from Highway 44 and 10 minutes from Purina. This house is an incredible one of a kind treasure with lots of unique features including: outdoor gazebo, fish pond, all original cedar interior design, two second story balconies, two large bat tubs (one located in the main bedroom) and so much more!!! Private parking and a gate for added privacy. Just minutes from Six Flags. Book today

301 Guesthouse- Historic Main street-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!

A Kirkwood Cottage, Quaint Suburb of St Louis
Quaint cozy cottage on a “No Thru Street”. The best place to stay in Kirkwood.This was my childhood home. Only 1/2 mile to downtown Historic Kirkwood with its many shops & restaurants,Farmers Market, Kirkwood Park & Pool & Train Depot. A couple of miles to Museum of Transport,Powder Valley Nature Center & Magic House Museum is a MUST if you have children. Home has steps to entry & is 4th house from railroad tracks that are up on the hill at end of street.Close easy access to all major highways

Serenity Valley (No Cleaning Fee- No pets please)
Discover Serenity in this 675 sq ft Studio cottage on a private wooded lot. Cozy space with 1 queen bed & optional inflatable queen bed for up to 4 guests. Relax on the patio, enjoy a bubble bath in the vintage clawfoot tub, or take in the panoramic woods view on the couch. Amenities include WIFI, washer/dryer, fully stocked kitchen, DishNetwork, pack&play. Just 60 mins from downtown STL, 15 mins from Washington, 20 minutes from Six Flags. Your tranquil escape awaits! No pets allowed.

Cozy Mid-Century Modern Townhome
This comfy 2 bedroom, 1.5 bath townhome is perfect for up to 5 guests. Luxury King bed in bedroom 1 and luxury Queen bed in bedroom 2. A futon in the living room can be used for a 5th guest. A pack-n-play is available upon request. This dynamic location is 5 minutes from bars, restaurants, shopping, Lindenwood University, and Ameristar Casino. It's only 2 miles from St. Charles, historic, Main Street, and it's only 15 minutes from the airport, and about 30 minutes from downtown St. Louis.

Charming Bungalow in Historic St. Charles, MO
This charming bungalow is located in the heart of Historic St. Charles, Missouri. Just blocks from Historic Main Street where you can enjoy dining & shopping from a variety of local businesses, as well as Frontier Park & the Katy Trail which are perfect for a stroll or bike ride! The bungalow is steps away from Lindenwood University, a short drive to Streets of St. Charles & Ameristar Casino, a 15 minute drive to St. Louis Lambert Airport, and a 30 minute drive to downtown St. Louis!

*HotTub* The Jewel on 5th-2br2b-near Historic Main
A true gem only a 15 min drive from the STL Airport. Enjoy a well equipped, century home a short 12 min walk to Historic Main and a HOTTUB. The large stocked kitchen is great for entertaining. Master bedroom w/luxurious, king sized, 4 poster bed and ensuite bathroom awaits you. In the private, queen suite you’ll find its own bathroom 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. Can sleep 6.

Bright & Cozy Shotgun DPX 1 Block from Historic DT
Admire this unique historic home's design with brand new amenities and antique details that give a fresh and charming feel. Built in the late 1800's, this half of the duplex has a typical shotgun layout with ten-foot ceilings giving a spacious feel. The front door leads directly to the living room, then into the bedroom, both of which have the original hard wood floors. The back of the house has the kitchen, with exposed brick, a dining area, and a bathroom with a washer and dryer.

Honeymoon Suite at Camp Skullbone In The Woods
Experience a romantic, quiet, and cozy chalet designed for two! This charming retreat features vintage décor and all the modern amenities you need for a comfortable stay. Unwind indoors by kicking back and watching a movie, surfing the web, curling up with a good book or a friendly board game, or sharing a drink with that special someone. In the evening, relax on the cozy deck under the stars, basking in the warm glow of the gas fire pit or unwinding in the inviting private hot tub!

Large Fenced Yard & Deck-Cozy Fam Friendly Home
**FAMILY FRIENDLY** (See details for the items avail for families) This 2 bedroom home has everything you need for a relaxing trip! Fully updated with stylish and comfortable furniture and decor. Fully equipped kitchen and an amazing backyard/deck. Quiet street by one of the best Mexican restaurants in St. Louis - Hacienda - (can walk 2 min there) Close to everything! 13 minutes to the St. Louis Zoo 10 minutes to The Magic House 15 minutes to Busch Stadium & Union Station
Popular amenities for Chesterfield house rentals
House rentals with a pool

Willow Creek: Mid-Century Oasis

Private indoor pool & sauna

Clark Brick House w/ Pool | Historic St. Charles

Blair's Pool House - Creve Couer Hot Tub Game Room

Arch View Luxury Home:Pool,Sauna,Free Wine &Brkfst

Spacious Family Home w/ Pool & Amazing Spaces

Wander Innsbrook Woods

Roomy Oasis with hot tub on the Hill!
Weekly house rentals

The Little House.

New: Cozy Cottage Near The Hill

Family Friendly Home Near Parks and Dining

Main Street Hideaway

The Ladybug Inn

Little Red House, Entire House in Tower Grove East

Comfy 3BR home in heart of Saint Peters

XMAS 365 - KING BED - Family Friendly
Private house rentals

Perfect Getaway 3BR/3BA Home

Luxurious, spa-like retreat steps from Main St.

Private Walkout w King Bed & Bath + large livingrm

3+ private acres, Koi fish pond, garage parking

Serene & Cozy Cabin + LAKE! Near Purina & SixFlags

Modern Country Oasis

Spacious Historic Townhouse - Character for All

🌟 Adorable Historic 🏠 in the ❤️ of St. Charles 🌟
Quick stats about house rentals in Chesterfield

Total vacation rentals
Explore 10 vacation rentals in Chesterfield

Nightly prices starting at
Chesterfield vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

Verified guest reviews
Over 70 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Wi-Fi availability
10 of Chesterfield vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Chesterfield rentals

4.8 Average rating
Chesterfield stays are highly rated by guests—averaging 4.8 out of 5!
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- Central West End
- Six Flags St. Louis
- Busch Stadium
- Saint Louis Zoo
- Enterprise Center
- City Museum
- Missouri Botanical Garden
- St. Louis Aquarium at Union Station
- Cuivre River State Park
- Pere Marquette State Park
- Castlewood State Park
- Meramec State Park
- Hidden Valley Ski Resort
- The Winery at Aerie's Resort
- Grafton Winery the Vineyards
- Cathedral Basilica of Saint Louis
- Raging Rivers WaterPark
- Norwood Hills Country Club
- Bellerive Country Club
- Saint Louis Science Center
- Adventure Valley Zipline Tours and Paintball Park
- Missouri History Museum
- Noboleis Vineyards
- Old Warson Country Club




