Vacation rentals in Winfield

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Top-rated vacation rentals in Winfield

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top 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, 750 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!

Guest favorite
Home in O'Fallon
4.92 out of 5 average rating, 51 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!

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, 331 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, 39 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, 96 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!

Guest favorite
A cabin is seen across a tranquil pond, surrounded by greenery and bare trees. The single-story structure features a front porch with chairs, reflecting off the water's surface. The gravel pathway leads from the cabin to the peaceful landscape.
Cabin in Wright City
4.88 out of 5 average rating, 17 reviews

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.

Guest favorite
Camper/RV in Fieldon
4.95 out of 5 average rating, 19 reviews

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.

Guest favorite
A comfortable living area is furnished with a dark green leather sofa and patterned chair. A wooden entertainment unit holds a television, while a lamp provides warm light. Natural wood accents are visible in the ceiling and decorative elements, enhancing a cabin-like ambiance.
Home in Wright City
4.84 out of 5 average rating, 107 reviews

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.

Top guest favorite
A cozy log cabin is set amidst tall trees, featuring a gabled roof and a stone foundation. The front porch is adorned with chairs and a charcoal grill, providing a shaded space. Surrounding greenery creates a tranquil, natural atmosphere.
Cabin in Brighton
4.97 out of 5 average rating, 110 reviews

Log Cabin with Breathtaking View

Relax, kick back and take in the view. Cozy log cabin nestled in the woods with a breathtaking view of a private 2 acre stocked fishing lake. Private master bedroom features queen sized bed, and attached bath. Loft sleeps four with two full beds and an air mattress. Full kitchen with stove, full size fridge, microwave and dishwasher. Living room with sofa and dining room. Charcoal Grill, fire pit, picnic area, and walking trails. Pets are welcome.

Top guest favorite
A living area is arranged with a light beige couch and two dark blue armchairs. A small table with a lamp is positioned nearby. The space features natural light filtering through sheer curtains, and artwork adorns the walls, adding a touch of color.
Home in Wentzville
4.91 out of 5 average rating, 178 reviews

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.

Top guest favorite
The living room area features a comfortable couch adorned with colorful cushions. A large television is mounted on the wall, while a small bar area with high stools provides a transition to the kitchen, which is visible in the background.
Home in St. Charles Historic District
4.99 out of 5 average rating, 108 reviews

Cottage on Historic Main St- Low Cleaning Fee

MESSAGE FOR SHORT STAY DISCOUNT Walk to everything on Historic Main Street St. Charles! Stay in a stylish 2BR steps from top dining, shops, nightlife & Ameristar Casino. 12 mins to STL Airport. Fast Wi-Fi, Smart TV, full kitchen, free parking & easy self check-in. Perfect for couples, weekend getaways & business stays. Unbeatable location, step outside directly onto Main Street in this vibrant, walkable district. Check out our 5★ reviews!

Guest favorite
A modern living area features a gray sofa facing large windows that allow natural light. Two armchairs are positioned beside a round coffee table, enhancing the space's openness. Light-colored curtains frame the windows, and a piece of wall art adds a touch of style.
Home in Grafton
4.96 out of 5 average rating, 74 reviews

Modern Grafton Townhouse

Enjoy this spacious modern townhouse in the heart of Grafton! Located behind the Grafton Winery and Brewhaus, this townhouse offers everything you need for your perfect getaway. Upgraded finishes and furnishings throughout, this home is a stylish retreat. Large TVs in the living room and bedroom, with a private home theater in the basement, perfect for a movie night! Fully stocked kitchen, laundry room, and two-car garage.

Popular amenities for Winfield vacation rentals

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