Holiday rentals in Winfield

Marvel spacious home, Game Room, central location

Welcome to the Marvel House – Your Perfect Getaway for Groups Up to 14! Imagine stepping into a home custom-designed for groups, families, and friends who want to create unforgettable memories together. This isn't just another rental, it's a 4-BDR, 3-bathroom haven featuring a stunning hand-painted Marvel mural in the living room. Whether you're planning a family reunion, gathering for a special occasion, this home delivers the space, comfort & amenities that make group travel feel effortless.

Family · Location · Quiet

Cozy cabin on farm near Jerseyville and Grafton IL

No cleaning fees! Relax in this cozy cabin on a 30 acre farm w/beautiful views & peaceful surroundings. Near shopping, wineries, nightlife, hunting & fishing. Abundant wildlife & farm animals-horses, cows, chickens, goats, sheep, geese. Two bedrooms (one in a spacious loft) with a queen sofa sleeper in the living room. Full kitchen w/dish washer. Fireplace & cathedral ceilings in living room. Full bath w/shower. Covered front porch. Screen porch off living area w/outdoor seating. Fire pit.

Family · Location · Comfort

Westhoff Cottage

Cozy 2BR O’Fallon home sleeps 6 adults plus children with 2 queen beds, pull-out sofa, floor mattress (great for kiddos!) & pack n play available upon request. Pet-friendly with large yard! Fast WiFi, fully stocked kitchen, flatscreens in every room. Super clean, quiet street, easy Highway 70 access and only 23 min to Lambert Airport. Perfect for families, business travelers, relocations & traveling nurses. Seamless check-in and affordable rates. Everything you need for a comfortable stay!

Value · Location · Cleanliness

Welcome to the "Blue House on Boone"

Country Cottage home with tons of charm that you cannot get in a Hotel Room !!! Great retreat whether you are in town for a conference, wedding or a just a vacation. Located off historic Main Street and just a couple of doors from Britton House the oldest residence in Lincoln County. Short walk or even shorter drive to The Factory and other wedding venues in our community. Enjoy the Cuivre River State Park or just simply relax in the back yard with nice patio, firepit and dining area.

Value · Family · Sleep quality

Spacious 6BR Retreat | Near I-64 & Weddings

Unwind in this modern smart home near Highway 64, offering a comfortable and convenient stay for families, groups, and guests attending nearby weddings. Cook in a fully equipped chef’s kitchen, enjoy eight 4K smart TVs, fast WiFi, and a dedicated workspace for remote work, all supported by smart technology for added comfort and ease. Conveniently located near dining, shopping, and popular attractions, and just 30 minutes from STL Airport, it offers a seamless, spacious, and cozy stay.

Family · Value · Laundry

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.

Value · Family · Hospitality

Cozy Cajun Rentals

This mobile home is in a peaceful, rural area with residential properties and natural surroundings. Foley is a small town in Lincoln County, offering a more laid-back lifestyle. The area is surrounded by farmland and wooded areas, providing opportunities for outdoor activities. Nearby amenities include parks and small shops in the town of Winfield and Elsberry, about 10 to 20 minutes away. While larger retail and dining options are Troy, O'Fallon & St. Peters Mo. are 20 to 30 minutes

Location · Value · Kitchen

70’s Park Side Cabin with Kayaks

Welcome to our renovated 1970’s park side cabin!  This cute cabin is located in Cuiver River State Park and is close by several wedding venues. The cabin is a three bedroom and two bath, which is great for family trips or just a weekend getaway. We highly suggest; hiking, biking, running, kayaking, fishing, and taking pictures in the park. Our park side cabin has a simi stocked kitchen to help ease your stay. We hope you enjoy all the improvements we have made in this unique cabin!

Family · Value · Cleanliness

Wentzville Modern House

Experience a stylish stay at this centrally located property in Wentzville, Missouri. Relax with your family. It features a fully equipped kitchen with everything you need to prepare meals. The house is highly convenient; you can walk just one block to reach nearby amenities—no car is needed! Within walking distance, you'll find Save A Lot, Dollar General, Subway, KFC, McDonald's, Stephanie's Italian Restaurant, Papa John's Pizza, and Speakeasy Bar.

Location · Family · Back garden

The Ladybug Inn

This stylish place to stay is perfect for group trips. I have personally renovated this entire ranch style home. It has plenty of room for the whole family! You will find everything you need for a comfortable stay. Conveniently located near the heart of Wentzville. I also have another location in O'fallon Missouri if this property is not available for the dates you are needing it. Please search Beautiful 2 bedroom ranch home in O'Fallon MO.

Location · Value · Parking

Hot Tub Gazebo | Fire Pit | 2 Kings | Sleeps 10

Built with families and groups in mind, this home features a hot tub beneath a private covered gazebo, a fire pit, a fenced backyard with a playset, and a lower-level Entertainment Room. Three main-level bedrooms, a private family suite downstairs, and two separate living areas give everyone room to spread out while staying together. Sleeps up to 10, an easy home base for exploring St. Louis, just minutes from historic Cottleville.

Family · Location · Hot tub

Family Friendly Home Near Parks and Dining

Enjoy a relaxing experience at our conveniently located home in St. Peters. This 3 bedroom 2.5 home is fully stocked and ready for your family to visit. The neighborhood is quiet and within walking distance of a lovely park with walking trails, a playground, and ball fields. We are also minutes away from groceries, dining, and the St. Peters Recplex. We cannot wait to welcome you to our space for your next get away!

Value · Location · Hospitality