Holiday rentals in Chesterfield

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!

Serenity Valley (No Cleaning Fee)

Discover Serenity in this 675 sq ft Studio cottage on a private wooded lot. Cozy space with 1 queen bed & optional inflatable queen bed for up to 4 guests. Relax on the patio in Adirondak chairs, enjoy a bubble bath in the vintage clawfoot tub, or take in the panoramic woods view on the couch. Amenities include WIFI, washer/dryer, fully stocked kitchen, DishNetwork, pack&play. Just 60 mins from downtown STL, 15 mins from Washington, 20 minutes from Six Flags. Your tranquil escape awaits!

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!

Historic Old St. Charles ~ Pop Lucks Guest Suite

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.

Fenton Oasis

Lovely, fully furnished private basement over 1800 sq ft in a single-family home. Features include a private heated pool, kitchen, bathroom with tub/shower, living room with fireplace and TV, bedroom with egress window, and a second sleeping area. Close to parks with canoeing, hiking, and biking trails. Easy access to Hwy 44, 270 & 30, restaurants, downtown St. Louis, and the airport. Close to hospitals. just 13 miles from Six Flags St. Louis and 18 miles from Hollywood Casino St. Louis.

Pet & Child Friendly*Great Location*Ideal 4 Groups

Welcome to Stay Awhile! This fun & eclectic home is located in a fantastic neighborhood, and no more than a 30 minute drive to almost anywhere in St. Louis. Perfect for families, groups & furry friends alike. Recently updated-everything is new from the super comfy memory foam beds to the Keurig. If you are looking for a relaxing & fun stay, filled with amenities, we have you covered! We have even incorporated a fun little “eye spy” game into the design of the house Intrigued? Read on...

St. Louis Home away from Home!

Our property is the perfect place for anyone looking for a peaceful stay in STL! This 4BR, 2.5 BA house gets amazing natural light throughout the day, and is nearly too cozy! Located 12 minutes from the airport, and near many of STL’s top attractions, our home is sure to leave you feeling refreshed after your stay! We’re a family that is dedicated to ensuring our guests enjoy the best experience possible. As local hosts, you can rest peacefully knowing that we are just a phone call away!

The Rose Cottage -a short walk to Historic Main St

The Cottage has a 2 guest maximum Updated 1 bedroom home a three minute walk from historic Main Street and festivals like Oktoberfest, Christmas Traditions and Festival of the Little Hills, the Lewis and Clark Boat House, Foundry Arts Center, Katy Trail and more! Located 10 minutes from the airport , 2 minutes from Ameristar Casino and Bass Pro Shop. 25 minutes from downtown St. Louis, The Arch, Forest Park, Zoo, Art Museum, History Museum and Busch Stadium-home of Cardinals Baseball!