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.

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Guest favourite
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, 445 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.

Guest favourite
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, 190 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 favourite
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, 114 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 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, 667 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 favourite
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, 118 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 favourite
A modern kitchen area features white cabinetry and a kitchen island with three cushioned stools. Pendant lights hang above the island, illuminating the space. A doorway leads to another room, with a glimpse of additional kitchen appliances visible in the background.
Flat in St. Charles Historic District
4.94 out of 5 average rating, 388 reviews

Christmas Getaway in Historic Old St. Charles

Welcome to Pop Luck's 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. Pop Luck's 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. Also, check out our sister suite The Ella Rose, right next door.

Guest favourite
A comfortable living area features a light-colored sofa adorned with patterned cushions. A stylish lamp stands beside the seating, while a vibrant area rug and a coffee table with decorative elements complete the space. The open layout leads to a kitchen visible in the background.
Flat in Forest Park South East
4.9 out of 5 average rating, 153 reviews

Groovy in the Grove 5 min to SSM

Welcome to Groovy in the Grove - your hip 1 bedroom hideaway with a parking pad in vibrant St. Louis! Situated a mere 5 minutes from SSM Hospital, this retro retreat combines '60s flair with modern comfort. Dive into the spirited local scene brimming with eclectic eateries, quirky shops, and electric nightlife. Your colorful getaway stands as a nostalgic haven in the heartbeat of the Grove, promising a unique and unforgettable stay. Let the groove get in and discover the charm of St. Louis!

Top guest favourite
A spacious studio apartment with yellow walls features wooden flooring and exposed beams. A dining table is set for four, while a living area includes a green recliner and a beige sofa. A queen bed is visible in the background, draped with blue curtains.
Loft in Southwest Garden
4.94 out of 5 average rating, 674 reviews

Historic loft living. Safe, central neighborhood

FULLY FURNISHED, cozy private studio apartment on the 3rd FL in the Southwest Gardens neighborhood next to the famous "Hill" area of South St. Louis. This elephant themed unit is walking distance from dozens of the best restaurants the area has to offer. Queen bed and love seat/fold out portable sleeps 3. *****we have 3 other private 5-star listings with the same amenities within our building. Go to my profile and scroll down to see them. We would love to host you in any of them.

Top guest favourite
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, 369 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 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
4.95 out of 5 average rating, 369 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.

Top guest favourite
A living room features exposed brick walls, a comfortable gray couch, and a black wicker chair. A flat-screen television is mounted on one wall, while natural light fills the space through two windows. A vibrant area rug adds color to the hardwood floor.
Home in Saint Charles
4.96 out of 5 average rating, 291 reviews

Bright & Cozy Shotgun DPX 1 Block from Historic DT

Admire this unique historic home's design with brand new amenities and antique details that give a fresh and charming feel. Built in the late 1800's, this half of the duplex has a typical shotgun layout with ten-foot ceilings giving a spacious feel. The front door leads directly to the living room, then into the bedroom, both of which have the original hard wood floors. The back of the house has the kitchen, with exposed brick, a dining area, and a bathroom with a washer and dryer.

Top guest favourite
An artistic space features vibrant murals and wall art, including a striking circular installation illuminated by blue and purple lights. The decor showcases a blend of abstract designs, providing a unique atmosphere. A polished pole stands at the center, complemented by geometric patterns on the wall.
Home in McKinley Heights
4.94 out of 5 average rating, 1,173 reviews

ArtBnB: Enjoy the Curated Comforts of Home

With easy highway access, and conveniently situated equidistance from Soulard, Lafayette Square, Tower Grove South, and Cherokee St, this custom designed space is not only an experience on its own, but a perfect base for exploring The Gateway City. Surround yourself with art, literature, and the homie comforts that set ArtBnB aside from staunch hotel chains. A lightly stocked kitchen, library, garden, patio, deck, grill, fire pit, wine rack, kennel, and toiletries are all included.

Popular amenities for Chesterfield family-friendly rentals

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 € 26 per night before taxes and fees

  • Verified guest reviews

    Over 60 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

  • 4.6 Average rating

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