Vacation rentals in Winfield

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Top-rated vacation rentals in Winfield

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Superhost
A spacious living area features a comfortable brown couch centered around a coffee table. A rustic fireplace is set against a brick wall, providing warmth. Light-colored walls and plenty of windows enhance the natural light flowing into the room.
Home in O'Fallon
4.88 out of 5 average rating, 409 reviews

Private Walkout w King Bed & Bath + large livingrm

Our house sits in a very quiet and safe neighborhood. When you stay with us you will enter through the walkout basement. You have full access to our very private downstairs apartment. This will enter you right into the very large living area. The master bedroom is complete with a King bed, black out curtains and walk-in closet. Attached is a full size bathroom with walk-in shower. Amenities include television, DVD, WiFi, Kuerig, mini-fridge and access to patio/porch with backyard fire pit.

Top guest favorite
A comfortable living room features a sectional couch, light hardwood flooring, and a patterned area rug. A flat-screen TV is mounted above a brick fireplace. Natural light enters through windows adorned with light curtains, while a dining area with chairs is visible in the background.
Home in Wentzville
4.95 out of 5 average rating, 121 reviews

Cozy Home in Wentzville Sleeps 6 + Game Room

Welcome to your home away from home in Wentzville, Missouri! Families and furry friends are welcome to our cozy, centrally located home. Sleeps 6- 1 King , 1 Queen, and 1 Sleeper Sofa Full sized bed Fully equipped Kitchen with everything you need to create a delicious meal, or a cup of coffee Game room and Laundry located in the basement- 60 game free play arcade machine and foosball! Roku friendly TV located in both bedrooms, living room and on the Patio Fully Fenced Yard with Fire Pit

Guest favorite
The charming front porch features a white wicker chair and a decorative wreath, inviting relaxation. Greenery surrounds the entryway, complemented by a well-maintained lawn. A gravel pathway leads from the porch to the driveway, creating a welcoming entrance to the guest house.
Home in Saint Charles
4.97 out of 5 average rating, 726 reviews

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!

Top guest favorite
A cozy cabin is nestled among tall trees, featuring a welcoming front porch and a green door. The surrounding lawn is well-kept, with open fields visible in the distance, creating a peaceful and serene setting.
Guesthouse in Jerseyville
4.96 out of 5 average rating, 184 reviews

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.

Top guest favorite
A private hot tub is illuminated with soft blue lights, surrounded by a wooden fence. String lights hang overhead, enhancing the evening ambiance. The area offers seating options, creating a cozy space for relaxation.
Cottage in Augusta
4.9 out of 5 average rating, 115 reviews

Romantic Augusta Cottage-Relax & get away!

This cottage is designed to strengthen and refresh couples looking for a getaway from busy life. Relax in the comfortable Living room or prepare a meal in the recently updated fully furnished kitchen. Enjoy your nights in the spacious bedroom furnished with a California King sized bed and TV in the room. Enjoy the private hot tub just steps from the door or use the BBQ pit to create a meal to enjoy together. Area restaurants, wineries & golf are just minutes away! You are sure to enjoy!

Superhost
Cabin in Wright City
4.88 out of 5 average rating, 25 reviews

Seclusion at its finest on 90+ Acres!

Tucked away on 90 acres of private land, this cabin offers the perfect blend of peaceful seclusion and modern comfort. Surrounded by open meadows and wooded landscapes, it’s a serene retreat where wildlife and quiet moments come naturally. However, shops and essentials are just 15–20 minutes away. With a private patio hot tub, fully equipped kitchen, and a cozy indoor fireplace a comfortable stay is ensured. This is an adults-only property. Pets are welcome. Two guest maximum. No hunting.

Guest favorite
Home in O'Fallon
4.93 out of 5 average rating, 44 reviews

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!

Top guest favorite
A charming blue cottage features a welcoming porch with white railings. The front yard is landscaped with green grass and a few small trees, while a sign reading 'Blue House on Boone' is placed on the lawn. Nearby houses exhibit similar historic architecture.
Bungalow in Troy
4.98 out of 5 average rating, 92 reviews

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.

Guest favorite
A treehouse-style rental is nestled among vibrant autumn foliage, with wooden steps leading up to the entrance. The structure features a private front porch, framed by surrounding trees and a gravel path, conveying a natural and serene atmosphere.
Guest suite in Dardenne Prairie
4.88 out of 5 average rating, 325 reviews

Treehouse Spa Suite

Treehouse Day Spa is nestled on 3 wooded acres in St.Charles County. There is a subdivision next to me but I have my trees!!! Get away from it all while being close to it all at the same time. Augusta wineries, Main Street St. Charles and the Streets of Cottleville are all within minutes of the location! There are two rental units in the treehouse: The spa suite and the penthouse. They each have a separate entrance and are private spaces. Recharge your battery! Regroup Relax Refresh

Top guest favorite
Home in Foley
5 out of 5 average rating, 35 reviews

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

Top guest favorite
Cabin in Troy
4.95 out of 5 average rating, 92 reviews

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!

Top guest favorite
A well-maintained, single-story home is shown from an aerial view. The brick exterior is complemented by a neatly trimmed lawn and mature trees surrounding the property. A small covered porch with seating is visible, along with a driveway leading to a single-car garage.
Home in O'Fallon
4.96 out of 5 average rating, 116 reviews

Family friendly 4bd home! Longer stays available!

Spacious, peaceful home with 4 bed,2.5 bath on court in O’Fallon MO. Furnished kitchen, deck grill/dining, tv in bdrms/living space, lower level living area & ping pong. Located near shopping, restaurants, bars, casinos, wineries, gyms, hospitals, sports complexes & major highways. Just a 30 minute drive to downtown St. Louis, Enterprise Center, Busch Stadium, Forest Park, Zoo & Arch, 15 minutes from Lambert Airport, Hollywood amphitheater. Quiet suburb of St Louis.

Popular amenities for Winfield vacation rentals

  1. Airbnb
  2. United States
  3. Missouri
  4. Lincoln County
  5. Winfield