Holiday rentals in Chesterfield
Find and book unique accommodation on Airbnb
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.
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!
Cottage on Main Street- Low Cleaning Fee
MESSAGE FOR SHORT STAY DISCOUNT Stay in the heart of Historic Downtown St. Charles! WALK EVERYWHERE at this beautifully updated 2BR/1BA blends modern comfort with charm just steps from Main Street. Walk to award-winning restaurants, unique boutiques, coffee shops, festivals, and riverfront views. Directly across from the Katy Trail, perfect for biking and morning strolls. Minutes to Ameristar Casino and 12 minutes to STL Airport. Fast Wi-Fi, cozy beds, and an unbeatable location. See you soon!
Blair's House in St. Charles - 4 bedroom 2.5 Bath
Welcome to Blairs House in St. Charles, MO near Hwy 364 Where we ensure you have a cozy stay every day. 4 Bed 2.5 Bath Home located in St. Charles, Missouri. Fully stocked home from the kitchen to the bedrooms, ensures a cozy stay every day. Relax in the living room or get right to work in the office. Check out the 60 in 1 old school arcade game on FREE play. Cook Thanksgiving dinner and serve the dining room! Close I-64, I-70 & Hwy 364 Check our profile for over 30 listings in the area.
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
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.
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
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.
Hillside Cabin on 43 Acres w/ Private Lake & View!
Free from modern distractions, this 1-bedroom, 1-bath cabin in the heart of wine country is the perfect place to unplug and reconnect with nature! Immersed in lush woodlands, this cabin comes with all the amenities needed for a peaceful retreat, including a fishing lake (no license required!), resident horses, and fully equipped kitchen. Watch the horses and sunrise from the porch swing before venturing off to the Katy Trail or head to one of the many wineries located just minutes away!
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.
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! 🚲
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
Popular amenities for Chesterfield holiday rentals
Other great holiday rentals in Chesterfield
Serene Stay in St Louis, MO
Classy + Fun 4bd/1.5bth | Patio Dining | Game Room
Fernweh
Country Quiet Suburban Haven
Your Quiet Home in the St. Louis Suburbs Awaits
Cabin+LAKE! Fish-swim-kayak*Near Purina & SixFlags
Westhoff Cottage
Castle Kearan
Frequently Asked Questions
What are the best places to stay in Chesterfield?
Stays in central Chesterfield are frequently suggested for convenient access to local dining, shops, and public spaces. The area near Chesterfield Amphitheater is known for entertainment and events, making it a popular option for visitors.
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.
What are some of the best things to do in Chesterfield?
Chesterfield has the Butterfly House in Faust Park, live performances at Chesterfield Amphitheater, and scenic walking paths in area parks. Art galleries and locally owned restaurants are often recommended for visitors interested in exploring community culture.
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.
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- Busch Stadium
- Central West End
- Six Flags St. Louis
- Saint Louis Zoo
- The Dome at America's Center
- Enterprise Center
- St. Louis Aquarium at Union Station
- Gateway Arch
- City Museum
- Missouri Botanical Garden
- Washington University in St Louis
- Meramec State Park
- Forest Park
- Hidden Valley Ski Resort
- Meramec Caverns
- Saint Louis University
- The Pageant
- Castlewood State Park
- Gateway Arch National Park
- Saint Louis Science Center
- Soulard Farmers Market
- Westport Plaza
- Missouri History Museum
- Fabulous Fox