Family-friendly vacation 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.

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Guest favorite
A well-lit guest room features tall vaulted ceilings with exposed wooden beams and skylights. A cozy bed is adorned with patterned bedding, while decorative plants are placed around the space. Large windows allow natural light to fill the room, complemented by soft curtains.
Home in Bevo Mill
4.91 out of 5 average rating, 443 reviews

Sunny South City Guest House

Newly-rehabbed & cozy guest house. Everything you need is located here in the historic Bevo Mill neighborhood. In the heart of south St. Louis city, you’re steps away from local businesses, including the picturesque, historical Das Bevo. Step into a vintage-styled oasis, featuring large windows with plenty of natural light, tall vaulted ceilings, comfy queen bed, unique fridge, breakfast bar, sizable bathroom with a large walk-in shower. Hang outside at the picnic table under cute string lights.

Top guest favorite
A wall clock with large numbers is mounted above a white cabinet featuring a rattan pattern. A sleek table lamp with a soft glow rests on the cabinet, beside a small stack of books and a tablet, creating a cozy reading nook.
Apartment in St. Charles Historic District
4.91 out of 5 average rating, 346 reviews

Christmas Getaway ~ Old St Charles, Missouri

Welcome to The Ella Rose Guest Suite! This adorable gem represents everything you love about Old St. Charles. This cozy suite is just steps away from the heart of Main Street, restaurants, and all the action St. Charles has to offer. The Ella Rose is a charming one-bedroom, with an open and airy living room and kitchen. It has natural light and high ceilings throughout. It's farmhouse cottage decor makes for a relaxing place to rest. Come sit and listen to the music of our outdoor bubbler rock.

Guest favorite
The exterior of the Pacific Palace showcases a unique wooden design with ornate decorations. Brightly colored adirondack chairs invite relaxation on the porch, while a stone pathway leads to the front door beneath a gabled awning. Lush greenery frames the playful architecture.
Home in Pacific
4.92 out of 5 average rating, 185 reviews

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

Top guest favorite
A rustic living area features a large stone fireplace with a cozy fire and a wall-mounted television displaying a program. Comfortable seating includes a grey sofa and a round table for dining. Decorative items add character to the room.
Guest suite in Saint Charles
4.93 out of 5 average rating, 112 reviews

The Luxury Lodge in St. Charles

The Luxury Lodge is a Private Residence at Rear of Property with Private Keypad Door Entrance, Private Parking, Outdoor Deck, Dog Run Line and 1/2 acre Fenced Backyard. Kick back & relax in this serene, spotlessly clean, stylish luxury & country living in St. Charles, MO w/ Great Scenic View. Dog friendly, comfy Queen Size Bed, Love Seat, Queen Sleeper Sofa, Large Stone Fireplace, Huge Bathroom, Rain Shower, Private Powder Room, Large Screen TV, Cable & Streaming, Kitchenette, Fridge & Dresser.

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, 666 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!

Top guest favorite
A log cabin with a dark metal roof is featured, accompanied by a covered porch area containing two chairs. Surrounding landscaping includes a well-maintained lawn and decorative stones, providing a natural setting that complements the cabin's rustic design.
Cabin in Pacific
4.99 out of 5 average rating, 115 reviews

Catch The Dream:; An Immersive Equestrian Escape

Welcome to the most serene and immersive equine retreat in the area! We are so happy you decided to stay with us. We want you to feel relaxed and at home as you enjoy the equine activities as well as the cozy log cabin and all its features and amenities! Enjoy views of the lush property and relax as you watch the horses graze and roam. We offer customized horsemanship opportunities that accommodate each person's level of comfort and ability. Cost: $75 for two hours, maximum of two lessons/day

Top guest favorite
A brick home with a sloped roof is shown from the front, featuring a pathway lined with greenery leading to the entrance. Two chimneys rise above, and the yard is well-maintained with shrubs and flowers. The sky is partly cloudy, adding to the serene ambiance.
Guest suite in Lindenwood Park
4.93 out of 5 average rating, 366 reviews

Home Suite Home

A NEIGHBORHOOD home with a small town vibe. NO PARTIES tolerated!!!!! OPEN ALL PHOTOS TO READ PHOTO DETAILS. A PRIVATE BASEMENT SUITE with: PRIVATE Entry, Living Room, Bedroom, Full Bath, Kitchenette, Yard/Patio; walk to Historic Route 66, restaurants, coffee shops, shopping, churches, parks/playgrounds/trails; 10-20 minutes from Lambert Airport, Downtown STL, historic neighborhoods, and major attractions; and major US Highways. *SEARCH from 3915 Watson Rd, 63109 for travel distances.

Top guest favorite
The exterior of a chalet is illuminated at night by warm string lights. Large windows reflect soft interior light, revealing a cozy atmosphere. The wooden deck is accessed by a railing, creating a welcoming entry. Trees are visible in the background, adding natural charm.
Home in Dittmer
4.96 out of 5 average rating, 545 reviews

Honeymoon Suite at Camp Skullbone In The Woods

Experience a romantic, quiet, and cozy chalet designed for two! This charming retreat features vintage décor and all the modern amenities you need for a comfortable stay. Unwind indoors by kicking back and watching a movie, surfing the web, curling up with a good book or a friendly board game, or sharing a drink with that special someone. In the evening, relax on the cozy deck under the stars, basking in the warm glow of the gas fire pit or unwinding in the inviting private hot tub!

Superhost
A bright and open living space is showcased, featuring a comfortable sofa and a television mounted above a cozy fireplace. A dining area with a wooden table is visible, adorned with a simple centerpiece. A staircase leads to the upper loft, enhancing the airy atmosphere.
Home in Soulard
4.85 out of 5 average rating, 479 reviews

The Soulard Cottage | There Is Only One

Built in 1894, this historic, free-standing Cottage is a staple in Soulard. The Soulard Cottage is steps away from McGurks, Dukes, Mollys and all of Soulard's hottest spots! Not to mention, less than a 8 minute Uber to The Arch, Busch Stadium (Cardinals), Enterprise Center (Blues), the City Museum, The Aquarium and so much more! Here for business? Perfect! Here for a game? Perfect! This cottage will give you a truly unique experience while you explore St. Louis.

Superhost
A single-story home is depicted with a metal roof and a front door featuring a decorative window. Brightly colored flower pots filled with blooms are arranged along the path, complemented by landscaped greenery surrounding the property.
Tiny home in Pacific
4.9 out of 5 average rating, 677 reviews

Route 66 Cozy Cottage

* Fast Wifi (Spectrum) * Keypad entry (no keys to keep track of) * Private driveway by the front door for easy access to carry luggage in and out * Huge yard for dogs, kids or even adults to play * Lovely outdoor patio with plenty of comfortable seating and beautiful landscaping * For the kiddos- toys, books, and games (puzzles and games for adults too) * Essentials for your furbabies as well - treats, leashes, food & water bowls, waste bags, towels

Top guest favorite
A comfortable living room features a blue sofa, accompanied by a green chair and a wooden dining table. Natural light enters through a window with patterned drapes, illuminating the neutral walls and a decorative area rug. A wall clock and framed art complete the space.
Apartment in Lindenwood Park
4.88 out of 5 average rating, 218 reviews

Warriors Rest and Repose in St. Louis Hills

This first floor apartment is part of a 4-unit building on Jamieson. It is in St. Louis Hills neighborhood, a community with grocery and retail stores on the main drags – Chippewa and Hampton, with easy reach to city parks and the River Des Peres Greenway Trail. It is well-placed for all city visitors, here for excursions or family get-togethers, medical visits or business travelers, where visitors can rest and repose for another day of fun!

Guest favorite
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
4.89 out of 5 average rating, 298 reviews

Treehouse Spa Suite

Treehouse Day Spa is nestled on 3 wooded acres in St.Charles County. 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

Popular amenities for Chesterfield family-friendly rentals

Quick stats about vacation rentals that are family-friendly in Chesterfield

  • Total vacation rentals

    Explore 20 vacation rentals in Chesterfield

  • Nightly prices starting at

    Chesterfield vacation rentals start at G$6,266 GYD per night before taxes and fees

  • Verified guest reviews

    Over 60 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Chesterfield vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chesterfield rentals

  • 4.6 Average rating

    Chesterfield stays receive an average rating of 4.6 out of 5 from guests