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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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Guest favorite
Home in Bevo Mill
4.91 out of 5 average rating, 452 reviews

Sunny South City Guest House

Newly-rehabbed & cozy guest house. Everything you need is located here in the historic Bevo Mill neighborhood. In the heart of south St. Louis city, you’re steps away from local businesses, including the picturesque, historical Das Bevo. Step into a vintage-styled oasis, featuring large windows with plenty of natural light, tall vaulted ceilings, comfy queen bed, unique fridge, breakfast bar, sizable bathroom with a large walk-in shower. Hang outside at the picnic table under cute string lights.

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
4.94 out of 5 average rating, 104 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

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, 166 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.

Guest favorite
Home in Grafton
4.94 out of 5 average rating, 16 reviews

Flynn Inn

River View – Walkable to Downtown Grafton-Bike Trail located across the Street- This updated 2-bedroom, 2-bath home offers detailed finishes and a relaxing river view. With two private bedrooms, a pull-out sofa, and space for 6 guests, it’s ideal for families or friends. Enjoy the oversized soaking tub, two expansive patios, and a large screened-in porch. Just a short walk to downtown Grafton’s shops, restaurants, and riverfront, this home provides the perfect mix of comfort and convenience.

Top guest favorite
A view from the living area into the bedroom, showcasing a serene space with a queen-size bed dressed in crisp white linens and accented by earthy throw pillows. Natural light illuminates the room, complemented by a ceiling fan and light-toned wooden flooring.
Apartment in North Hampton
4.99 out of 5 average rating, 185 reviews

The Zen Den - Centrally Located, Calm and Tranquil

The Zen Den was conceptualized out of a desire to create a calm and peaceful oasis centrally located in the North Hampton neighborhood of St. Louis where parks, cafés, restaurants, and entertainment are only minutes away. The space features modern appliances, contrasted with soft light features and natural building materials, such as reclaimed lumber, to convey a sense of calm and tranquility. Ideal for those guests seeking to retreat at the end of a busy day exploring or remote working.

Superhost
A well-lit interior space features warm wooden flooring and a soft area rug. Natural light filters in from a nearby window, enhancing the inviting atmosphere of the room. The layout suggests a cozy and functional space suitable for relaxation or entertaining.
Home in St. Louis
4.79 out of 5 average rating, 231 reviews

Cheerful 1-bedroom, red brick, historic home

Keep it simple at this peaceful, historic, and centrally-located place. This red brick home is a piece of long-standing history (built in 1928), on a quiet one way street. It is just 5 minutes away from the airport & University of Missouri Saint Louis, and just 15 minutes from down town and central west end. It is literally central to just about any place you wish to visit in the Saint Louis area! There’s convenient and free on-street parking too! Come enjoy your time at The Ruby Brick Stay!

Top guest favorite
A historic two-family brick home is set amidst a lush green lawn, framed by flowering plants. The building features a pitched roof and multiple windows that enhance natural light. A welcoming walkway leads to the entrance, showcasing the charm of the surrounding neighborhood.
Condo in Saint Charles
5 out of 5 average rating, 27 reviews

Historic 2nd Street Petite Maison

Your family will be close to everything when you stay here. Walk to parks, the Katy Trail is right across the street. Bikes are available to rent nearby. Walk to historic Main Street, bakeries, restaurants, festivals, breweries, and more. The Saint Charles Trolley is free and you can catch it nearby. Close to Main Street, Ameristar Casino, St. Charles Convention Center and the Family Arena. 30 minutes to downtown St. Louis and 20 minutes to Zoo, Forest Park, and Delmar Loop.

Guest favorite
A bright bedroom is visible featuring a queen bed dressed in white linens. Two nightstands with lamps are positioned on either side of the bed. A painting hangs above the bed, and natural light streams in through window treatments.
Home in Saint Charles
5 out of 5 average rating, 8 reviews

Separate Entry Basement Apartment 1BR, 1BA

This private lower level with separate entry is located in the safe city of St. Charles, MO on about 0.5 an acre of land in a quiet neighborhood with easy highway access for quick commutes. We are central to many shopping and dining options in the area and about half an hour from downtown St. Louis. Recently upgraded internet will make working from home and streaming easy. As travelers ourselves, we are happy to provide you with a welcoming and comfortable place to stay while in town!

Guest favorite
A mobile home is set in a rural landscape, featuring a covered porch with stairs leading to the entry. The exterior is painted in light blue, surrounded by lush greenery and trees. Sunlight filters through the leaves, illuminating the spacious yard.
Home in Foley
5 out of 5 average rating, 20 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
The exterior of the cabin is presented, featuring a mix of wood and siding in earthy tones. Large windows allow natural light to flood the interior, and a wooden deck is visible, bordered by a landscaped area of stones. Trees surround the home, enhancing the peaceful atmosphere.
Cabin in Troy
4.94 out of 5 average rating, 84 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
The exterior features a basement-level entrance framed by a concrete pathway. Large windows provide natural light, while a well-maintained grassy area surrounds the entrance. The building's siding is light-colored, and a light fixture is mounted above the door.
Guest suite in Florissant
4.83 out of 5 average rating, 144 reviews

Peaceful lower level apt in wooded neighborhood

A self contained apartment located in the basement of our home. 2 private entrances, self check-in and check-out. The neighbors in our cul-de-sac are trees and cardinals (the birds not the baseball players.) Quiet enough to work, work, work. Spacious enough to play, play, play. Christian Hospital 6 min, Airport 17 min, Busch Stadium 24 min, Convention Plaza 24 min, Downtown St. Louis 25 min. Very near nature reserves and confluence of Missouri and Mississippi Rivers.

Top guest favorite
A queen-sized bed is featured with a patterned grey bedspread, positioned near a window with wooden blinds. A cozy chair sits in the corner, accompanied by decorative elements, including a globe and a travel-themed sign, enhancing the room's inviting atmosphere.
Guest suite in Weldon Spring
4.94 out of 5 average rating, 71 reviews

Wanderlust

The whole group will enjoy easy access to everything from this centrally located living space. It is located only 10 minutes from the wineries, 8 minutes from the outlet mall, and 15 minutes from downtown St. Charles. With 920 square feet of living space, this dwelling also offers a kitchenette, living room, and game area. There is a full-sized pool table, ping pong table, and foosball table. There is also access to a hot tub and fire pit upon request.

Popular amenities for Winfield vacation rentals

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