Family-friendly vacation rentals in Chesterfield

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.

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!

Centrally Located Mid-Century Modern Retreat

Make yourself at home in the thoughtfully restored historic apartment located in the heart of St. Louis City which boasts both historic and modern elements. You will be minutes away from all major highways, eateries, attractions, and entertainment the city has to offer. "Come stay at this mid-century modern retreat, you'll be central to everything St. Louis has to offer and I'm committed to making your stay the best and safest possible using an enhanced cleaning process! " - Sean, Your Host

Charming Pop Lucks Guest Suite in 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.

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

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.

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.

Cozy Studio in Beautiful New Town St. Charles

Stay at this cozy studio centrally located in the amazing community of New Town St. Charles. New Town is a large scale new urbanist community built on the edge of suburbia. You never have to leave New Town with its walkability to restaurants, bars, a market, coffee shops, ice cream, food kiosk, canals, lakes, parks and tree lined streets. If you do leave its only a few miles from historic St. Charles Main street, The Streets of St. Charles, and 25 miles to Downtown St. Louis.

Home Suite Home

A NEIGHBORHOOD home with a small town vibe. NO PARTIES tolerated! OPEN ALL PHOTOS for 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, attractions; and 4 US Highways. *SEARCH from 3915 Watson Rd, 63109 for travel distances.

Large, Woodsy, Warm and Inviting | Cozy 2BR Apt

Tucked in a quiet neighborhood near the Delmar Loop, this 2-bedroom, 1-bath apartment offers a stylish and comfortable retreat. Enjoy a fully stocked kitchen with stainless steel appliances, a record player, and a 55” Google TV for streaming. Step outside to a shared patio with seating, outdoor dining, and a kids’ playground. Additional amenities include a dedicated workspace and in-house washer/dryer.

The Benton House - With fenced yard!

Built in 1926 in the heart of Historic St. Charles, The Benton House was renovated with a modern, yet spunky, twist. It's conveniently located steps from Main Street shopping/restaurants/nightlife, and the St. Charles Convention Center! The Benton House is pet-friendly, also perfect for families with kids, couples, friends, business travel, bridal, bachelorette or bachelor's.

Cozy Retreat | Charming Apt. near Top Attractions!

Indulge in a tranquil and chic retreat within this inviting space. We welcome you to our fully furnished apartment in the heart of Saint Louis. Nestled in a secure neighborhood, you'll enjoy both serenity and convenience, as we are only a short 15-minute drive from downtown St. Louis and just 10 minutes away from Forest Park. Perfectly situated to explore the city of St. Louis.