Holiday rentals in Winfield

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

Location · Value · Condition

Quiet 2BR Retreat on 7 Acres | Sleeps 6, Fast WiFi

Perfect for families, couples, or work trips, this private 2-bedroom apartment offers a peaceful retreat on 7 acres —just a short drive from Wentzville or Troy. Enjoy a spacious layout, fast WiFi, and a quiet setting ideal for relaxing or getting work done. The private driveway, entrance, and patio make this in-law suite a space of its own. The location in a quiet neighborhood just off Hwy 61 provides privacy and convenience. ⭐ Rated 5.0 by guests for cleanliness, comfort, and communication.

Value · Location · Nearby

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.

Location · Family · Accuracy

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 · Parking

Kayleigh’s Kottage

Warm and cozy 3 bedroom barn/cottage that has a rustic hip vibe that will make you feel right at home !!! Just outside city limits and placed on nearly an acre of ground with rural setting Great kitchen with basics taken care of for ya ! Living area is open to kitchen and dining area. The bedrooms on main level are large and comfy queen beds, ceiling fans and tvs. lower level has bonus 3rd bedroom, family room, private bath with shower. 2 car garage is available Laundry facilities in basement

Family · Location · Nearby

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 · Family · Heating

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.

Location · Family · Layout

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 · Sleep quality

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!

Value · Family · Kitchen

Spacious 6BR Retreat | Near I-64 & Weddings

Enjoy a comfortable stay in this modern smart home near Highway 64, ideal for families, groups, and guests attending nearby weddings. Cook in a fully equipped gourmet kitchen, enjoy eight 4K smart TVs, reliable WiFi, and a dedicated workspace for remote work, all enhanced 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 smooth, spacious, and inviting stay.

Location · Value · Layout

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!

Family · Value · Kitchen

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.

Location · Family · Decor