Family-friendly holiday rentals in Chesterfield

A well-organized kitchen features dark cabinetry and a light countertop, providing ample workspace. A comfortable couch is positioned in the living area, absorbing natural light from the window. Decorative elements, including a round wall mirror and soft furnishings, add a touch of warmth to the space.

4.92 out of 5 average rating, 119 reviews

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!

4.94 out of 5 average rating, 369 reviews

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

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!

4.96 out of 5 average rating, 109 reviews

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.

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.

4.97 out of 5 average rating, 760 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!

4.92 out of 5 average rating, 236 reviews

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

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

4.99 out of 5 average rating, 125 reviews

Home in Ballwin

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.

4.91 out of 5 average rating, 308 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.

4.93 out of 5 average rating, 229 reviews

A well-lit bedroom features a spacious bed adorned with soft linens and decorative pillows. A wooden nightstand holds a small vase with flowers. Natural light filters through two windows, framed by dark curtains, illuminating the warm tones of the wooden flooring.

Home in Dogtown

Cozy Cottage in a Quiet City Neighborhood!

Please inquire for longer stay rates. This 650sq.ft quaint cottage has EVERYTHING! Centrally located this sought after historical neighborhood, DOGTOWN!, is just minutes from Forest Park and a short drive to all of STL's BEST ATTRACTIONS! This charmer has all the amenities you could hope for @ your HOME away from home! 2 Bedrooms with a Queen Bed in each, 3 Smart TV's, a backyard patio, KEYLESS Self Entry, fully equppied kitchen with SS appliances, MAIN FLOOR LAUNDRY and fully UPDATED BATH!

Guest suite in Dardenne Prairie

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.

4.88 out of 5 average rating, 338 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

4.95 out of 5 average rating, 144 reviews

Cabin in Defiance

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!

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.

4.81 out of 5 average rating, 180 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.