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Holiday rentals in Chesterfield

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Quick stats about holiday rentals in Chesterfield

  • Total holiday rentals

    Explore 30 holiday rentals in Chesterfield

  • Nightly prices starting at

    Chesterfield holiday rentals start at £37 per night before taxes and fees

  • Verified guest reviews

    Over 370 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of Chesterfield holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chesterfield rentals

Top-rated holiday rentals in Chesterfield

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A spacious sleeping area features a large bed adorned with plush white pillows. Shelves display vintage cameras and decorative items, while ambient lighting is created by lamps on side tables. The walls are painted a soft blue, adding to the room's calm ambiance.
Tiny home in Pacific
4.94 out of 5 average rating, 361 reviews

Route 66 Railroad Shanty, a cozy artsy small space

This 536 s.f. house, believed to have once been a sleeping shanty for railroad crews switching shifts for the night. Fully renovated and updated in 2021 by a local artist, you will find custom metal art throughout, granite countertops and a very warm cabin feel featuring a kitchen and bathroom finished with locally sourced Missouri dark red cedar, 10 minutes from six flags, Purina farms 15 min from hidden valley and 45 min from downtown this place is in a great location and will not disappoint!

Top guest favourite
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, 754 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 favourite
A well-lit living area features a dark leather sofa adorned with colorful cushions, complemented by a wooden coffee table and a blue area rug. Artwork and decorative accents enhance the space, with sunlight filtering through the windows, creating a warm, inviting atmosphere.
Flat in Maryland Heights
4.88 out of 5 average rating, 200 reviews

Stunning Modern Apt| King bed 5 min CreveCoeurLake

Experience luxury and style in our St. Louis home. This second-floor residence features 2 modern bedrooms, a cozy living room, a fully equipped kitchen, a stylish bathroom, and a dedicated workspace with high-speed WiFi- blending comfort and elegance. Located in a secure Maryland Heights community, just minutes from Creve Coeur Lake, Westport Plaza, Hollywood Casino & Amphitheatre, and historic St. Charles. With plush bedding, premium amenities, and ample parking, we promise a seamless stay!

Top guest favourite
Home in Saint Charles
4.91 out of 5 average rating, 304 reviews

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.

Guest favourite
Flat in Kirkwood
4.94 out of 5 average rating, 141 reviews

2026 Sale! Charming Kirkwood (2) Bedroom

Welcome to this cozy home-away-from-home, designed with the Airbnb guest in mind! Minutes from downtown Kirkwood and 20 minutes from downtown STL it is perfect for those traveling for work or fun! Guests are provided internet, hotel linens, & laundry access. Settle in & enjoy cooking in the kitchen, relaxing in the living room, and resting in your hotel-inspired bedrooms. This listing was converted from a shared apartment to a full unit in August 2024. Prior reviews are for one bedroom.

Guest favourite
A treehouse-style rental is nestled among vibrant autumn foliage, with wooden steps leading up to the entrance. The structure features a private front porch, framed by surrounding trees and a gravel path, conveying a natural and serene atmosphere.
Guest suite in Dardenne Prairie
4.88 out of 5 average rating, 333 reviews

Treehouse Spa Suite

Treehouse Day Spa is nestled on 3 wooded acres in St.Charles County. There is a subdivision next to me but I have my trees!!! Get away from it all while being close to it all at the same time. Augusta wineries, Main Street St. Charles and the Streets of Cottleville are all within minutes of the location! There are two rental units in the treehouse: The spa suite and the penthouse. They each have a separate entrance and are private spaces. Recharge your battery! Regroup Relax Refresh

Superhost
A grey sectional sofa is positioned next to a circular glass table, creating a comfortable seating area. Natural light floods the space through large glass doors leading to the outside. A potted plant adds greenery, while wall decor spells out 'HOME.'
Home in St. Louis
4.89 out of 5 average rating, 140 reviews

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!

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
4.87 out of 5 average rating, 136 reviews

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.

Top guest favourite
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, 432 reviews

*NEW HotTub* The Jewel on 5th-2br2b-near 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.

Superhost
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
4.83 out of 5 average rating, 178 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.

Top guest favourite
The exterior of a historic log cabin features a welcoming yellow door and a decorated porch with a small table and chairs. Lush greenery surrounds the cabin, while vibrant flowers add a touch of color. The structure is complemented by the clear blue sky.
Cabin in Saint Charles
4.98 out of 5 average rating, 385 reviews

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! 🚲

Top guest favourite
The exterior of a contemporary single-story house is displayed, featuring a light-colored facade with dark accents. A two-car garage is visible, along with a small front garden. Clear skies and green trees surround the property, suggesting a peaceful residential setting.
Home in O'Fallon
4.95 out of 5 average rating, 144 reviews

Family friendly 3bd home! Longer stays available

Peaceful, 3 bed, 2 bath on court in O’Fallon MO. Furnished kitchen, deck grill/dining, tv in bdrms/living space, lower level living area & ping pong. Serene, fenced in back yard for your morning coffee. 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..

Popular amenities for Chesterfield holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Chesterfield

Guest favourite
A spacious bedroom is presented with a large bed dressed in crisp white linens. Two armchairs provide seating beside a window, which is framed by natural light. Minimalist artwork adorns the walls, complemented by soft lighting from bedside lamps.
Home in Saint Charles
4.88 out of 5 average rating, 78 reviews

Blairs House 4 Bed 3 Bath - Sleeps 8

Top guest favourite
The kitchen features wood cabinets and a spacious countertop. Modern appliances include a stainless steel gas stove, built-in microwave, and dishwasher. A full-size refrigerator is present. Natural light is provided through two windows, with a small plant hanging nearby.
Home in Ballwin
4.93 out of 5 average rating, 70 reviews

Cozy & Comfortable home in a quiet neighborhood.

Top guest favourite
Home in Saint Charles
5 out of 5 average rating, 23 reviews

Country Quiet Suburban Haven

Top guest favourite
Home in Wildwood
4.99 out of 5 average rating, 100 reviews

3+ acre, fast wi-fi, rustic timber frame, Koi pond

Guest favourite
A modern living area features large windows allowing natural light and views of the surrounding trees. Plush seating surrounds a circular table, and a spiral staircase leads to the upper level. The outdoor space includes a grill and seating arranged around a fire pit.
Home in Gray Summit
4.96 out of 5 average rating, 47 reviews

Cabin+LAKE! Fish-swim-kayak*Near Purina & SixFlags

Guest favourite
Home in O'Fallon
4.92 out of 5 average rating, 53 reviews

Westhoff Cottage

Top guest favourite
Farm stay in Saint Charles
5 out of 5 average rating, 55 reviews

The Farmhouse Inn

Guest favourite
A spacious living area features two navy blue sofas, each adorned with decorative pillows. A round coffee table with a gold finish sits on a patterned area rug. The background shows an open dining space with a modern light fixture.
Home in O'Fallon
4.93 out of 5 average rating, 14 reviews

Spacious 3BR Ranch Near I-64 & Hwy K

Frequently Asked Questions

  • What are the best things to do in Chesterfield with kids?

    Kids often enjoy exploring the Butterfly House, playing at local playgrounds in Central Park, or learning at The Magic House’s satellite location. Seasonal outdoor concerts and hands-on nature experiences are also popular family activities.

  • How is the weather in Chesterfield?

    Chesterfield has cold winters, with lows around 24°F (−5°C), and warm, humid summers reaching up to 90°F (32°C). Spring and fall see milder temperatures with occasional rain, making these seasons pleasant for outdoor exploration.

  • When is the best time to visit Chesterfield?

    Late spring and early autumn are often recommended for mild temperatures and local festivals. Many visitors enjoy outdoor events, blooming gardens, and comfortable walks during these seasons.

  • What are the best places to visit in Chesterfield?

    Faust Park with its historic village and Butterfly House, plus Chesterfield Amphitheater for outdoor shows, are frequently recommended. Art enthusiasts might enjoy local galleries, and green spaces provide scenic relaxation.

  • What are some hiking trails in Chesterfield?

    Explore the scenic trails at Faust Park, including forested paths and accessible loops, or wander the multi-use trails in River's Edge Park. The area’s parks are great places for walking, jogging, and spotting local wildlife.

  • What are some family activities we can do in Chesterfield?

    Families can enjoy the Butterfly House, playgrounds at Central Park, and interactive exhibits at The Magic House. Outdoor concerts, walking trails, and picnic areas add more ways to connect and unwind together.

  • What are some of the best day trip ideas from Chesterfield?

    Explore the Missouri Wine Country nearby, spend time at sophisticated museums and cultural sites in Saint Louis, or enjoy hiking in Castlewood State Park. Antique shops and scenic parks in nearby towns also draw many travelers.

  • Are there any pet friendly accommodations available in Chesterfield?

    Travelers with pets can find many stays in Chesterfield that welcome four-legged companions, often with easy access to parks and walking trails. Check for listings that specify pet-friendly amenities or fenced outdoor space.

  • What are some local tips for visiting Chesterfield?

    Layered clothing helps with changing weather, especially in transitional seasons. Consider checking local event schedules for concerts or markets, and try exploring parks early in the day for a quieter atmosphere.

  • What is Chesterfield known for?

    Chesterfield is known for its vibrant parks, family-friendly attractions, and strong arts scene. The area draws visitors for outdoor festivals, green spaces, and its locally rooted shopping and dining.

  • What are the best hidden gems to explore in Chesterfield?

    Lone Elk Park is often noted for wildlife viewing and tranquil walking paths, while local art galleries display works from Midwestern artists. Small cafés and specialty shops around the city also offer relaxing atmospheres and unique finds.

  • What are the best foods to try in Chesterfield?

    Visitors can explore Midwestern comfort foods, seasonal barbecue, and toasted ravioli, a local specialty. The city also has popular bakeries, international restaurants, and casual steakhouses with regional flavors.

  • What should I bring for a trip to Chesterfield?

    Pack layers and a light rain jacket for variable weather, especially in spring or fall. Comfortable walking shoes are helpful, as Chesterfield has several parks and trails perfect for outdoor activities.

  • What is the nightlife in Chesterfield like?

    Chesterfield has a lively night scene centered around casual bars, local music venues, and neighborhood eateries. Many spots feature live performances, relaxed patios, and locally brewed drinks, creating a welcoming place to unwind.

  • What are the most popular events or festivals in Chesterfield?

    Chesterfield celebrates local culture with events like the Chesterfield Summer Concert Series and seasonal festivals around Faust Park. Art shows and community markets are frequently suggested in spring and fall.

  • Are there family friendly vacation rentals in Chesterfield?

    Chesterfield has vacation rentals suited for families, including spacious homes and apartments with features like full kitchens or access to parks. Many neighborhoods are near green spaces, making it convenient for travelers with children.

  • How much does it cost to stay in apartment rentals in Chesterfield?

    Experience the best of Chesterfield with our apartment rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • 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.

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