
House holiday 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.

BEAUTIFUL Historic 3 Bedroom Upscale Guesthouse!!
Spacious luxury three bedroom home in historic St. Charles. Minutes away from Main Street, Frenchtown, Streets of St. Charles, shopping, and more. The bright, fully equipped chef's kitchen features a gas range, spacious counters, and upscale appliances for all your dining and entertainment needs. Bedrooms include luxury DreamCloud Mattresses and upscale bedding. Full size washer/dryer, walk in closet, and Roku. Dream bathrooms with soaker tub. Backyard features outdoor relaxation and playhouse.

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

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.

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!

Tompkins Street Retreat
Relax in this two-bedroom, two-bath house with a backyard patio and firepit with a privacy fence. Walk to unique shopping and entertainment on Historic St. Charles Main Street. Local wineries and St. Louis attractions are a short drive away. Enjoy a comfortable living room with a large TV and a fully equipped kitchen for special meals. Unwind after an active day with a meal, drinks under the pergola, and a great night's sleep in our king-size bed. We also offer FREE off-street/garage parking.

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!

Wooded 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.

Great Fam Friendly Home w/ Lrg Deck & Yard
**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

The Frenchtown Inn | 2BR Charmer
Welcome to the Frenchtown Inn on the corner of Third and French! Experience the best of St. Charles in this charming 2-bedroom, 2-bathroom house situated in the heart of Frenchtown. This delightful space offers a perfect blend of comfort, convenience, and a touch of history, ideal for an unforgettable stay. We are dog friendly, complete with a fenced in yard. The Frenchtown Inn awaits you. Come experience a memorable, relaxing getaway with family or friends in our inviting home!
Popular amenities for Chesterfield house rentals
House rentals with a pool

Willow Creek: Mid-Century Oasis

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

T | Pool · Hot Tub · Arcade · 4BR Luxury Retreat

Honeymoon Suite at Camp Skullbone In The Woods

"The Villa" at Villa Augusta in MO wine country

Spacious Home - Heated Pool Open - Amenity Packed

Roomy Oasis with hot tub on the Hill!

Sunset Mountain Privacy
Weekly house rentals

Serenity Valley• Secluded Escape • No Cleaning Fee

Family friendly 3bd home! Longer stays available

Cozy Home in Wentzville Sleeps 6 + Game Room

ArtBnB: Enjoy the Curated Comforts of Home

Updated 1913 Home in Historic Saint Charles

Sunny South City Guest House

Sparkling Vintage Charmer, King Bed, Quiet Comfort

Safe home in a quiet neighborhood near I 44
Private house rentals

Serene Stay in St Louis, MO

The Niederschulte House

Cozy & Comfortable home in a quiet neighborhood.

Classy + Fun 4bd/1.5bth | Patio Dining | Game Room

Luxurious, spa-like retreat steps from Main St.

Private Walkout w King Bed & Bath + large livingrm

Your Quiet Home in the St. Louis Suburbs Awaits

Serene & Cozy Cabin + LAKE! Near Purina & SixFlags
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 $56 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

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!
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- Busch Stadium
- Central West End
- Six Flags St. Louis
- Saint Louis Zoo
- Enterprise Center
- St. Louis Aquarium at Union Station
- The Dome at America's Center
- City Museum
- Missouri Botanical Garden
- Meramec State Park
- Gateway Arch National Park
- Gateway Arch
- Castlewood State Park
- Washington University in St Louis
- Forest Park
- The Pageant
- Cathedral Basilica of Saint Louis
- Saint Louis University
- Saint Louis Science Center
- Saint Louis Art Museum
- Soulard Farmers Market
- Fabulous Fox
- Missouri History Museum
- Meramec Caverns





