House vacation rentals in Chesterfield

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Top-rated house rentals in Chesterfield

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Top guest favorite
A comfortable living room features a sectional couch, light hardwood flooring, and a patterned area rug. A flat-screen TV is mounted above a brick fireplace. Natural light enters through windows adorned with light curtains, while a dining area with chairs is visible in the background.
Home in Wentzville
4.94 out of 5 average rating, 109 reviews

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

Top guest favorite
Home in Ballwin
4.99 out of 5 average rating, 113 reviews

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.

Top guest favorite
The charming front porch features a white wicker chair and a decorative wreath, inviting relaxation. Greenery surrounds the entryway, complemented by a well-maintained lawn. A gravel pathway leads from the porch to the driveway, creating a welcoming entrance to the guest house.
Home in Saint Charles
4.97 out of 5 average rating, 704 reviews

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!

Guest favorite
A spacious bathroom features a freestanding bathtub surrounded by natural stone walls. A walk-in shower with a glass panel is visible alongside a modern sink. Warm lighting hangs above, and a potted plant adds a touch of greenery, enhancing the serene atmosphere.
Home in University City
4.92 out of 5 average rating, 145 reviews

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.

Guest favorite
A charming exterior is shown, featuring a light blue façade with white trim. Windows are framed with dark shutters. A small white picket fence surrounds the front yard filled with greenery and plants, while a wreath decorates the door, enhancing the home's welcoming appearance.
Home in St. Charles Historic District
4.94 out of 5 average rating, 180 reviews

Charming 2/1 in St Charles Historic Main Street

Come relax and play! Half a block from historic Main Street in City of St Charles. This stay is everything you could want. Cozy, charming, private with outdoor area for seating and dinning table. Off-street parking, laundry. Go shopping in the historic downtown shops, go to concerts, casinos or just stay in and enjoy! Walk to restaurants and the Katy Trail! Come be our guest! Or stay in put and cook the kitchen has everything you need! We are a strictly non smoking stay, inside or outside.

Guest favorite
The living room showcases a blend of seating options, including a black futon and a brown leather sofa, complemented by a colorful area rug. Natural light filters through patterned curtains, illuminating the space which features a television and decorative touches.
Home in Saint Charles
4.95 out of 5 average rating, 131 reviews

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.

Superhost
The modern home features a spacious wooden deck with steps leading to a well-maintained garden. Large glass doors dominate the front facade, allowing natural light to flood the interior. Lush trees provide a serene backdrop, complementing the inviting outdoor space.
Home in Fairview Heights
4.89 out of 5 average rating, 115 reviews

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.

Guest favorite
The exterior of a charming century home showcases a covered front porch with white railings and a welcoming entrance. Lush greenery and flower beds line the stone steps leading to the porch, enhancing the inviting character of the property.
Home in Saint Charles
4.94 out of 5 average rating, 394 reviews

*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.

Guest favorite
A cozy living room features a large gray sectional sofa, complemented by two wooden chairs. Natural light enters through sheer window coverings, illuminating the space. A light-colored rug adds texture underfoot while artwork decorates the walls, enhancing the room's comfortable atmosphere.
Home in Saint Charles
4.85 out of 5 average rating, 155 reviews

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.

Superhost
A cozy living area is presented with a gray sofa layered with patterned cushions. A light gray coffee table is centered on a soft area rug, while a dark stone fireplace serves as a focal point. Natural light filters through two windows covered by bamboo shades.
Home in Saint Charles
4.9 out of 5 average rating, 145 reviews

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

Top guest favorite
Home in O'Fallon
4.96 out of 5 average rating, 109 reviews

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.

Top guest favorite
The exterior of the house features a well-maintained lawn with shrubbery and a covered porch. A cozy seating area with a modern coffee table is shown, complemented by a sectional sofa. A well-equipped kitchen with appliances and a dining table set for six are also visible. A serene bedroom showcases a spacious bed with soft linens.
Home in Saint Charles
4.99 out of 5 average rating, 193 reviews

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!

Popular amenities for Chesterfield house rentals

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 G$8,368 GYD per night before taxes and fees

  • Verified guest reviews

    Over 80 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • 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!