Family-friendly holiday rentals in Saint Charles

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. See you soon!

Indoor spaces · Kitchen · Cleanliness

BEAUTIFUL Historic 3 Bedroom Upscale Guesthouse!!

Spacious luxury three bedroom home in historic St. Charles. Minutes away from Main Street, Frenchtown, Streets of St. Charles, shopping, and more. The bright, fully equipped chef's kitchen features a gas range, spacious counters, and upscale appliances for all your dining and entertainment needs. Bedrooms include luxury DreamCloud Mattresses and upscale bedding. Full size washer/dryer, walk in closet, and Roku. Dream bathrooms with soaker tub. Backyard features outdoor relaxation and playhouse.

Kitchen · Family · Condition

The Welcoming Retreat 8 Beds 5BR 2.5Bathroom

Centrally Located Home in Historical St. Charles MO. Perfect for guest seeking to be close to everything. Near Lindenwood University, Historic Main Street, Katy Trail & Streets of St. Charles, with a diverse choice of Restaurants & daily activities. You will feel right at home in this private 8 Beds, 5BR, 2.5 Bath getaway. The Welcoming Retreat is set up for Weekend Escapes Multi-Family get togethers Sporting Events, Special Occasions or Groups. Close access to HWY 70 & St. Louis Lambert Airport

Indoor spaces · Kitchen · Cleanliness

Main Street Hideaway

This house is located on historic Main Street in Saint Charles, Missouri. This means we are within walking distance of dozens of restaurants and boutique shops. We are in the wedding district and three wedding venues are within a 5 minute walk: The Old Stone Chapel & LaBelle Couer. This is the perfect spot for bridal parties and families. This unique house, is a perfect spot for a bridal party to get ready and prepare for the big day. Brand new bath added in 2024. Outdoor patio new in 26

Kitchen · Indoor spaces · Hospitality

Tompkins Street Retreat

Relax in this two-bedroom, two-bath house with a backyard patio and firepit with a privacy fence. Walk to unique shopping and entertainment on Historic St. Charles Main Street. Local wineries and St. Louis attractions are a short drive away. Enjoy a comfortable living room with a large TV and a fully equipped kitchen for special meals. Unwind after an active day with a meal, drinks under the pergola, and a great night's sleep in our king-size bed. We also offer FREE off-street/garage parking.

Indoor spaces · Family · Access

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.

Family · Indoor spaces · Condition

Sweet Escape Near Historic Main St, 4BR, 2 Baths

Discover your Sweet Escape in this charming 4-bedroom bungalow, just a 3-minute drive (or 20-minute walk) to Historic Main Street’s cobblestone streets, boutique shops, dining, and events. Now featuring two full bathrooms, including a newly added second-floor bath for extra convenience. Enjoy a game-filled basement with pool table, ping-pong, foosball, and darts, plus yard games, a fire pit, and cozy nights with board games and DVDs. Sleep soundly on plush beds with room-darkening curtains.

Kitchen · Indoor spaces · Sleep quality

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.

Family · Kitchen · Walkability

*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.

Family · Kitchen · Getting around

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.

Kitchen · Indoor spaces · Bathroom

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! 🚲

Family · Kitchen · Air conditioning

The Frenchtown Inn | 2BR Charmer

Welcome to the Frenchtown Inn on the corner of Third and French! Experience the best of St. Charles in this charming 2-bedroom, 2-bathroom house situated in the heart of Frenchtown. This delightful space offers a perfect blend of comfort, convenience, and a touch of history, ideal for an unforgettable stay. We are dog friendly, complete with a fenced in yard. The Frenchtown Inn awaits you. Come experience a memorable, relaxing getaway with family or friends in our inviting home!

Kitchen · Family · Location