Family-friendly holiday 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.

Private Walkout w King Bed & Bath + large livingrm

Our house sits in a very quiet and safe neighborhood. When you stay with us you will enter through the walkout basement. You have full access to our very private downstairs apartment. This will enter you right into the very large living area. The master bedroom is complete with a King bed, black out curtains and walk-in closet. Attached is a full size bathroom with walk-in shower. Amenities include television, DVD, WiFi, Kuerig, mini-fridge and access to patio/porch with backyard fire pit.

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 and a golf cart!

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.

The Zen Den - Centrally Located, Calm and Tranquil

The Zen Den was conceptualized out of a desire to create a calm and peaceful oasis centrally located in the North Hampton neighborhood of St. Louis where parks, cafés, restaurants, and entertainment are only minutes away. The space features modern appliances, contrasted with soft light features and natural building materials, such as reclaimed lumber, to convey a sense of calm and tranquility. Ideal for those guests seeking to retreat at the end of a busy day exploring or remote working.

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

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.

Entire lower level of our home w/Paris Theme

Our home is located in a quiet West St. Louis County neighborhood. The lower/walkout of this place is your home away from home. It has a private entrance from a walk around sidewalk to the backyard. You will have the entire lower level of our home. We live in the upstairs or first floor of this home. Our place is best suited for one couple, solo adventurers, business travelers, and one family (with kids). This space has been recently remodeled with a French Parisian theme!

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.

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.