
House holiday rentals in Chesterfield
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Top-rated house rentals in Chesterfield
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Cozy Home in Wentzville Sleeps 6 + Game Room
Welcome to your home away from home in Wentzville, Missouri! Families and furry friends are welcome to our cozy, centrally located home. Sleeps 6- 1 King , 1 Queen, and 1 Sleeper Sofa Full sized bed Fully equipped Kitchen with everything you need to create a delicious meal, or a cup of coffee Game room and Laundry located in the basement- 60 game free play arcade machine and foosball! Roku friendly TV located in both bedrooms, living room and on the Patio Fully Fenced Yard with Fire Pit

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.

Katy Trail Farmhouse - 3 bd/2.5 bath - Amazing!
DIRECTLY ON THE KATY TRAIL! Quaint 1943 farmhouse on 7 private acres in Missouri wine country - halfway between Klondike Park & the town of Augusta. Loads of farmhouse charm w/ the amenities & comforts of home. Spacious & well-appointed, 3 bedrms/2.5 baths. Walk-in/out or bike-in/out to KATY trail -- the location is perfect. Enjoy a sunset dinner & live music at one of the many wineries – or relax on one of the two screened-in porches & clear your mind. No other place like it in Augusta!

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!

Tranquil three-bedroom home in central St. Louis
Welcome to Spa 7748! Relax and enjoy the quiet, tranquil space we have to offer you. Three bedrooms, two full baths, laundry room, work out area, media/office area, fully equipped chef’s kitchen, two fireplaces, covered patio, outdoor fire pit, driveway parking, and street parking. Centrally located in University City, which is just minutes from the downtown Clayton business/entertainment district, Washington University, Fontbonne University Downtown STL, Central West End, The Grove, Dogtown.

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.

St. Louis Home away from Home!
Our property is the perfect place for anyone looking for a peaceful stay in STL! This 4BR, 2.5 BA house gets amazing natural light throughout the day, and is nearly too cozy! Located 12 minutes from the airport, and near many of STL’s top attractions, our home is sure to leave you feeling refreshed after your stay! We’re a family that is dedicated to ensuring our guests enjoy the best experience possible. As local hosts, you can rest peacefully knowing that we are just a phone call away!

Relaxing Oasis with Free Bottle of wine+brkfst
Enjoy serenity and tranquility at our modern home tucked away in a private setting just 5 short minutes from Downtown St Louis. Complementary bottled water, continental breakfast(packaged muffins) and a bottle wine will pamper you the moment you arrive.Unwind in our luxurious multifunction shower+memory foam mattress Test your swing on our scenic driving mat or unwind around the crackling outdoor fire pit. Spa and Special Occassion add-on packages available. Private off street parking.

*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.

Family/4bd/2bth/Huge Yard/Playset/Ping-Pong/Arcade
Our freshly updated and furnished house is ready for the family with kids, the adult getaway, and wedding parties from Stone House event venue across the street! Boasting tons of privacy, a huge yard with a playset and games, a fully stocked kitchen with everything you could want for a Thanksgiving dinner, and a large basement with arcade boxes, ping pong, weights, and seating areas. A very safe and secluded location that is close to amazing parks, restaurants, wineries, and shopping.

Updated 1913 Home in Historic Saint Charles
Walking distance to Main Street, Saint Charles puts you close to restaurants, shops, and antique stores. A lovely coffee shop and breakfast restaurant are right around the corner. This home sits on a spacious double lot which gives you plenty of room to enjoy the backyard and amenities. Please note: although we have 4 queen beds and 1 queen pull-out couch, there is only 1 bathroom. This home is over 100 years old, we hope you will enjoy it, but keep that in mind! Permit #23-0478

Family friendly 4bd home! Longer stays available!
Spacious, peaceful home with 4 bed,2.5 bath on court in O’Fallon MO. Furnished kitchen, deck grill/dining, tv in bdrms/living space, lower level living area & ping pong. Located near shopping, restaurants, bars, casinos, wineries, gyms, hospitals, sports complexes & major highways. Just a 30 minute drive to downtown St. Louis, Enterprise Center, Busch Stadium, Forest Park, Zoo & Arch, 15 minutes from Lambert Airport, Hollywood amphitheater. Quiet suburb of St Louis.
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

Honeymoon Suite at Camp Skullbone In The Woods

"The Villa" at Villa Augusta in MO wine country

Spacious Home - Central Location - Amenity packed

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

Modern Oasis fire pit and hot tub

ArtBnB: Enjoy the Curated Comforts of Home

Dogtown Century home near Forest Park & Maplewood

The Ladybug Inn

Safe home in a quiet neighborhood near I 44

Bright & Cozy Shotgun DPX 1 Block from Historic DT

3+ private acres, Koi fish pond, garage parking

Two King and Two Twin Beds in French Town
Private house rentals

Eureka Garden of Life 73

The Niederschulte House

Cottleville Corner

Cozy & Comfortable home in a quiet neighborhood.

Luxurious, spa-like retreat steps from Main St.

Serene Corner Cottage with Hot Tub

Comfy Digs + Game Room Bliss

Scenic River Home
Quick stats about house rentals in Chesterfield

Total holiday rentals
Explore 10 holiday rentals in Chesterfield

Nightly prices starting at
Chesterfield holiday rentals start at $57 AUD per night before taxes and fees

Verified guest reviews
Over 80 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Chesterfield holiday 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!
Destinations to explore
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- Central West End
- Busch Stadium
- Six Flags St. Louis
- Enterprise Center
- Saint Louis Zoo
- St. Louis Aquarium at Union Station
- City Museum
- Hidden Valley Ski Resort
- Gateway Arch National Park
- Castlewood State Park
- Meramec State Park
- The Dome at America's Center
- Cathedral Basilica of Saint Louis
- Washington University in St Louis
- Saint Louis Science Center
- Gateway Arch
- Forest Park
- Saint Louis University
- Stifel Theatre
- Missouri History Museum
- Laumeier Sculpture Park
- Soulard Farmers Market
- Fabulous Fox
- The Pageant




