Holiday rentals in Chesterfield

301 Guesthouse- Historic Main street-Katy Trail

Our small 301 Guest House was 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!

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!

Cozy & Comfortable home in a quiet neighborhood.

Relax with the family or friends in our quaint home. We have 3 bedrooms which will sleep 6 comfortably. In the kitchen you have a full size fridge, gas stove, built in microwave, and a dishwasher. There is a breakfast bar that has 3 stools. Comfy living room with full size couch and oversized chair with a large tv to relax in. Fenced backyard with private patio that offers a bbq bit, and firepit for those chilly evenings. Tons of restaurants along with work out facilities within 3 miles.

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.

*NEW HotTub* The Jewel on 5th-2br2b-near 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.

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.

Private 3-Acre Retreat • Koi Pond & Waterfall

Escape to Rick’s Retreat, a private 3+ acre wooded getaway in Wildwood, MO. Enjoy a beautiful koi pond and waterfall, wraparound deck, fire pit, grill, pool table, and spacious timber-frame home. With 4 bedrooms, 5 beds, and room for up to 9 guests, there’s plenty of space to relax and reconnect. Babler State Park is just 1 mile away, with Chesterfield Valley, restaurants, shopping, and St. Louis attractions a short drive away. Perfect for families, friends, and weekend getaways!

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!

Blair's Jungle House w/ Hot Tub - Game Room

Welcome to Blairs Jungle House in St. Peter's, MO. Bring the family, plenty of room to spread out and relax. Newly renovated 4 Bed 3 full Bath with Game Room in LL & Hot Tub! Please come and enjoy your stay. Kitchen is fully stocked with all the essentials for casual cooking or thanksgiving dinner. Whether you're in the mood to relax or hang out in the Game Room, Blair's House has you covered. Close I-70 & 364 Check out our profile for more listings.

Hot Tub Gazebo | Game Room | 2 Kings | Sleeps 8

A spacious, fully stocked home with a hot tub beneath a private covered gazebo, a fire pit, a lower level game room, and a big fenced backyard. Send the kids downstairs to the arcade and indoor swing while the adults soak under the gazebo, or make it home base for a wedding at nearby Stone House. Two king beds, a bunk room kids love, and a kitchen ready for real cooking, all in a quiet St. Charles neighborhood near restaurants, wineries, and parks. Sleeps 8.

Great Location Fam Friendly Home w/Lrg Fenced Yard

Newly finished basement with 4th bedroom (King bed), large play/relaxation space & large 120-inch projector screen and separate large speaker for movie nights! Beds are all brand new comfortable memory foam! This house is in such a great and convenient area! Freshly renovated with all brand new beds and furniture, a fully stocked kitchen for cooking and baking and a fenced in pet friendly backyard! TONS of kids and baby items!

Country Quiet Suburban Haven

Welcome to our Country Quiet Suburban Haven—a spacious, comfortable 4-bedroom home in peaceful St. Charles, MO. With room for up to 9 guests, this inviting house offers modern amenities, cozy gathering spaces, and easy access to local dining and attractions. Located near The Katy Trail, historic downtown St Charles, and about a half hour from downtown St Louis, it’s perfect for families, groups, or extended stays.