
Family-friendly holiday rentals in Chesterfield
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Chesterfield
Guests agree: these family-friendly homes 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!

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

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!

*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.

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

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!

Blair's Jungle House w/ Hot Tub - Game Room
Welcome to Blairs Jungle House in St. Peter's, MO. Bring the family, plenty of room to spread out and relax. Newly renovated 4 Bed 3 full Bath with Game Room in LL & Hot Tub! Please come and enjoy your stay. Kitchen is fully stocked with all the essentials for casual cooking or thanksgiving dinner. Whether you're in the mood to relax or hang out in the Game Room, Blair's House has you covered. Close I-70 & 364 Check out our profile for more listings.
Popular amenities for Chesterfield family-friendly rentals
Family-friendly home rentals with a hot tub

Country Private Suite, L Level, Laundry, Hot Tub

Pool, Hot Tub and Dog Paradise

Spacious home with entertainment room and hot tub

Honeymoon Suite at Camp Skullbone In The Woods

Romantic Augusta Cottage-Relax & get away!

Secluded Lakeside Lodge Minutes from St. Louis

Cozy winter ranch on wooded land near shopping

Pere Ridge Tree Escape with private hot tub
Family- and pet-friendly home rentals

The Benton House - With fenced yard!

Family friendly 3bd home! Longer stays available

ArtBnB: Enjoy the Curated Comforts of Home

The Ladybug Inn

Spacious Home - Heated Pool Open - Amenity Packed

Sparkling Vintage Charmer, King Bed, Quiet Comfort

The Frenchtown Inn | 2BR Charmer

Stunning Modern Apt| King bed 5 min CreveCoeurLake
Family-friendly home rentals with a pool

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

First floor pet friendly family suite near Purina

Early Check-in, Late Check-out on Weekends 8AM-8PM

Peaceful Lakefront Chalet w/Dock and Boats!

Pura Vida Chalet - Lakefront on Lake St. Gallen

Resort Style Burb Suite 20mins/DT/Extended Stays

Secluded Property w Pool and Hot Tub

Innsbrook Luxe Escape - Spacious Retreat, Hot Tub
Quick stats about holiday rentals that are family-friendly in Chesterfield

Total holiday rentals
Explore 20 holiday rentals in Chesterfield

Nightly prices starting at
Chesterfield holiday rentals start at $51 SGD per night before taxes and fees

Verified guest reviews
Over 70 verified reviews to help you choose

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Chesterfield holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chesterfield rentals
Destinations to explore
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- Busch Stadium
- Central West End
- Six Flags St. Louis
- Saint Louis Zoo
- Enterprise Center
- St. Louis Aquarium at Union Station
- City Museum
- The Dome at America's Center
- Missouri Botanical Garden
- Hidden Valley Ski Resort
- Gateway Arch National Park
- Meramec State Park
- Castlewood State Park
- Gateway Arch
- Washington University in St Louis
- Forest Park
- Cathedral Basilica of Saint Louis
- Saint Louis Science Center
- Saint Louis University
- Missouri History Museum
- The Pageant
- Saint Louis Art Museum
- Soulard Farmers Market
- Meramec Caverns





