Holiday rentals in Chesterfield

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!

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!

"The Villa" at Villa Augusta in MO wine country

Villa Augusta is a Tuscan inspired home atop a hill on 30 acres in beautiful MO wine country. The location is perfect to experience the best of wine country with many wineries just 5-10 miles away. There are 2 separate and private spaces for guests to enjoy Missouri Wine Country. Enjoy the 2BR/2BA known as "The Villa" on the entire 2nd floor, or check out "The Cellar." our other listing. Return from a day enjoying the wineries or biking the Katy Trail and relax in the pool, spa or fireside.

Pop Lucks Guest Suite 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.

Patio House, secluded in heartbeat of Main Street

The Patio is nestled in the heart of historic St. Charles a few steps from Main Street, Katy Trail, Missouri River, Antique and Boutique Shopping, Restaurants Bars and More, Several Wedding venues are within walking distance of the property as well. In addition to your well appointed unit, this property has as much outside as it does in. Take your coffee, wine, water and enjoy our patio, complete with fire table, dining table edged with lush plantings for privacy. PLEASE NOTE NO SMOKING

*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.

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! 🚲

Luxury Modern Apt| KingBed| 5 Min Creve Coeur Lake

Discover your ideal getaway in this beautifully renovated 2-bedroom apartment, nestled in a charming building in Maryland Heights. Perfectly located just minutes from Creve Coeur Lake, Hollywood Casino & Amphitheater, and the historic streets of St.Charles, you'll enjoy effortless access to a wide array of dining and entertainment options. Whether you're planning a weekend escape or an extended stay, this thoughtfully designed space ensures comfort and relaxation at every turn.

Historic Bungalow

1929 Historic Bungalow. This historic 4 Bdrm house , 2 bedroms are on the main level, with the full size bathroom, 2 bedrooms are on the top level, has a fully equipped kitchen, a family room, laundry facility is in the lower level, covered patio. There is easy access from parking to entering the house. Central Heat and a/c, Wifi, 2 smart tvs with roku, comfybeds, very clean,4 blocks from Historic Main Street, Katy trail, Chicken n Pickle Convention center is close too!

Little House By Main St -5 4K TV's- 1-75 Inch -1GB

Little House By Main St -5 4K TV's- 1-75 Inch -1GB Internet- No location has better access to so much. All the best amenities on both sides of Main Street St Charles! Walking distance from the Ameristar Casino, Texas Road House, Main Street (Honky Tonk, Big A's, Q, Thirstys), Starbucks, Taco Bell, Buffalo Wild Wings, McDonald's and the Bars / Restaurants on Main. An Awesome Location for all of the Festivals in St Charles! And secured parking in the 1 car garage!

The Farmhouse Inn

Welcome to our beautifully renovated farmhouse, where modern comfort meets peaceful country charm. Nestled in the country side of rural St. Charles, located conveniently just 7 miles away from Historic Main Street. The house is pet-friendly, a perfect retreat for families, couples, or friends looking to slow down and enjoy wide-open spaces. The Farmhouse Inn was built in the late 1880's featuring a fully equipped kitchen, 2 bedrooms, 3 beds, and 3 bathrooms.

Cottage on Historic Main St- Low Cleaning Fee

MESSAGE FOR SHORT STAY DISCOUNT Walk to everything on Historic Main Street St. Charles! Stay in a stylish 2BR steps from top dining, shops, nightlife & Ameristar Casino. 12 mins to STL Airport. Fast Wi-Fi, Smart TV, full kitchen, free parking & easy self check-in. Perfect for couples, weekend getaways & business stays. Unbeatable location, step outside directly onto Main Street in this vibrant, walkable district. Check out our 5★ reviews!