Holiday rentals in Winfield

Secluded Lake House on a 13 acre private lake

Looking for a quiet place to relax and get away! Come stay on our 40-acre farm and unwind at our lake house where you can enjoy fishing, hiking, canoeing, and more! Enjoy sitting out on the brand new deck overlooking the lake, watching the Eagles and other wildlife. Sit around the fire on the deck or build your own fire down by the lake. Enjoy the boathouse where you can sit and relax right on the lake. Close to town. Note: There is no wifi. This is truly a place where you can unplug!

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!

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.

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!

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.

Hillside Cabin on 43 Acres w/ Private Lake & View!

Free from modern distractions, this 1-bedroom, 1-bath cabin in the heart of wine country is the perfect place to unplug and reconnect with nature! Immersed in lush woodlands, this cabin comes with all the amenities needed for a peaceful retreat, including a fishing lake (no license required!), resident horses, and fully equipped kitchen. Watch the horses and sunrise from the porch swing before venturing off to the Katy Trail or head to one of the many wineries located just minutes away!

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

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!

Pura Vida Chalet - Lakefront on Lake St. Gallen

Pura Vida Chalet is a lakefront, 2 bedroom + loft, 2 bath A-frame on Lake St. Gallen at Innsbrook Resort. This updated chalet sleeps up to 8 people (6 adults maximum). It sits on a 3-acre, semi-private, lakefront lot with breathtaking views of the lake. Onsite amenities include kayaks, stand-up paddle boards, jon boat with trolling motor, lily pad, fire pit, tree house, large deck and private dock, indoor wood-burning fireplace and screened-in porch. See more on IG @ChaletPuraVida

Private Cabin on 90 Acres!

Escape to this cozy one-bedroom cabin, perfectly tucked away in the middle of 90 acres of seclusion. With only one other cabin on the entire property, a quiet, relaxing stay is guaranteed. Through the gated entrance, a hidden pond adds to the tranquil atmosphere. The cabin features a cozy fireplace and a fully equipped kitchen. Out on the patio, your private hot tub under the stars awaits. This is an adults-only getaway. Pets are welcome. Maximum of two guests allowed. No hunting.

Waterfront Vintage Camper with Hot Tub

Escape to Beatrice, a beautifully restored 1969 Vintage Globe Star camper at The Last Resort glamp-ground. Enjoy a private hot tub, outdoor projector, and a 1.5-acre fishing pond. Nestled just 10 mins from Pere Marquette State Park and 12 mins from Grafton, IL, this unique nature retreat comfortably sleeps up to 4 adults or a family of 5. Perfect for glamping, wildlife viewing, and stargazing. Experience vintage charm with modern comforts in a serene, park-like setting.

Country home L Level, private, kitchen, hot tub

Very private country setting just 2 miles south of interstate 70. You’ll likely enjoy some wildlife sightings. Nice private patio seating. Cabin feel, spacious, has full kitchen. Murphy bed in the living room (very comfortable) provides an extra Q bed if needed, otherwise it’s out of the way. Internet was weak so affected some reviews but is super fast now. Nearby destinations are Cedar Lake Winery, Big Joel’s Safari, Long Row Lavender Farm, and Pumpkins Galore.