
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.

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

Catch The Dream:; An Immersive Equestrian Escape
Welcome to the most serene and immersive equine retreat in the area! We are so happy you decided to stay with us. We want you to feel relaxed and at home as you enjoy the equine activities as well as the cozy log cabin and all its features and amenities! Enjoy views of the lush property and relax as you watch the horses graze and roam. We offer customized horsemanship opportunities that accommodate each person's level of comfort and ability. Cost: $75 for two hours, maximum of two lessons/day

Camp Mill Pond: Historic Cabin Near Main Street
*St. Louis Magazine A-List Winner!* ***PRESS: DESIGN STL, STL MAG, AND FOX2NEWS*** Camp Mill Pond is a throwback to the slow and easy rhythm of hot summer days. This circa 1835 cabin offers easy access to our historic area, including Main Street, Katy Trail for biking, and Frenchtown, without sacrificing modern comforts! This 180-year-old historic cabin sits on a beautiful lot, shared with our 1865 three-story home and a two-story carriage house. Ask about renting bikes and a golf cart!

Romantic Augusta Cottage-Relax & get away!
This cottage is designed to strengthen and refresh couples looking for a getaway from busy life. Relax in the comfortable Living room or prepare a meal in the recently updated fully furnished kitchen. Enjoy your nights in the spacious bedroom furnished with a California King sized bed and TV in the room. Enjoy the private hot tub just steps from the door or use the BBQ pit to create a meal to enjoy together. Area restaurants, wineries & golf are just minutes away! You are sure to enjoy!

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.

Patio House, secluded in heartbeat of Main Street
The Patio is nestled in the heart of historic St. Charles a few steps from Main Street, Katy Trail, Missouri River, Antique and Boutique Shopping, Restaurants Bars and More, Several Wedding venues are within walking distance of the property as well. In addition to your well appointed unit, this property has as much outside as it does in. Take your coffee, wine, water and enjoy our patio, complete with fire table, dining table edged with lush plantings for privacy. PLEASE NOTE NO SMOKING

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.

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, pack&play. Just 60 mins from downtown STL, 15 mins from Washington, 20 minutes from Six Flags. Your tranquil escape awaits! No pets allowed.

Little House By Main St -5 4K TV's- 1-75 Inch -1GB
Little House By Main St -5 4K TV's- 1-75 Inch -1GB Internet- No location has better access to so much. All the best amenities on both sides of Main Street St Charles! Walking distance from the Ameristar Casino, Texas Road House, Main Street (Honky Tonk, Big A's, Q, Thirstys), Starbucks, Taco Bell, Buffalo Wild Wings, McDonald's and the Bars / Restaurants on Main. An Awesome Location for all of the Festivals in St Charles! And secured parking in the 1 car garage!

Beautiful Condo in New Town St. Charles
Location-Location! The condo is located in the heart of New Town, only a short walk to grab a bite to eat, volleyball courts, the coffee shop, Marsalas market, event tent, New Town amphitheater, parks, etc. The condo has a modern but cozy decor with updated furnishings. Enjoy coffee or drinks on the large deck. All basic amenities are provided for your stay. Monthly discounts offered for short term leases great for out of town workers, traveling nurses, etc.
Popular amenities for Chesterfield vacation rentals
Other great vacation rentals in Chesterfield

Travel w/ Kids | Modern Spacious 3-Story STL Home

Home away from Home St. Louis Cnty Ladue Schools

Luxurious Downtown Loft Steps From City Museum

The Niederschulte House

Cozy Cottage Home in New Town St. Charles

The Ladybug Inn

Long Stay Discounts~Fenced~Pets Welcome

Stunning Modern Apt| Kingbed -5 min CreveCoeurLake
Frequently Asked Questions
Are there family-friendly vacation rentals in Chesterfield?
Chesterfield has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in apartment rentals in Chesterfield?
Experience the best of Chesterfield with our apartment rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Chesterfield?
Four-legged friends are welcome in Chesterfield. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Chesterfield?
Yes! Work meets play with ease at over 20 vacation rentals in Chesterfield featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Chesterfield vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Chesterfield, available on Airbnb. Make a splash and soak up the sun in style!
Where should I stay in Chesterfield?
Make yourself at home in Chesterfield by choosing from our most frequently booked neighborhoods. We have over 40 vacation rentals in Brook Hill Estates, and over 40 vacation rentals in Meadowbrook Country Club Estates.
Do apartment rentals in Chesterfield have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Chesterfield. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Chesterfield have a kitchen?
Absolutely! We offer over 10 apartment rentals with a kitchen 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.
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.
Quick stats about vacation rentals in Chesterfield

Total vacation rentals
Explore 40 vacation rentals in Chesterfield

Nightly prices starting at
Chesterfield vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

Verified guest reviews
Over 320 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

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

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

4.6 Average rating
Chesterfield stays receive an average rating of 4.6 out of 5 from guests
Destinations to explore
- Chicago Vacation rentals
- Nashville Vacation rentals
- Platteville Vacation rentals
- Indianapolis Vacation rentals
- Downtown Chicago Vacation rentals
- Southern Indiana Vacation rentals
- St. Louis Vacation rentals
- Louisville Vacation rentals
- Kansas City Vacation rentals
- Branson Vacation rentals
- Memphis Vacation rentals
- Lake of the Ozarks Vacation rentals
- Busch Stadium
- Central West End
- Six Flags St. Louis
- Enterprise Center
- Saint Louis Zoo
- St. Louis Aquarium at Union Station
- City Museum
- Missouri Botanical Garden
- Hidden Valley Ski Resort
- Gateway Arch National Park
- The Dome at America's Center
- Meramec State Park
- Castlewood State Park
- Cathedral Basilica of Saint Louis
- Gateway Arch
- Washington University in St Louis
- Saint Louis Science Center
- Forest Park
- Saint Louis University
- Stifel Theatre
- Missouri History Museum
- Soulard Farmers Market
- Laumeier Sculpture Park
- Fabulous Fox




