Holiday rentals in Winfield

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Top-rated holiday rentals in Winfield

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Guest favourite
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, 402 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 favourite
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, 115 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 favourite
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, 715 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 favourite
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.
Guest house in Jerseyville
4.96 out of 5 average rating, 181 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 favourite
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, 321 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

Guest favourite
Home in Foley
5 out of 5 average rating, 31 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 favourite
The treehouse is illuminated at night, highlighting its modern architecture nestled among trees. Warm lights glow from the windows, contrasting with the dark sky. Surrounding foliage displays vibrant orange hues, adding a serene ambiance to the outdoor setting.
Treehouse in Hermann
4.99 out of 5 average rating, 133 reviews

Out On A Limb Treehouse

A unique Treehouse, 6 miles from Hermann, MO, offers a luxury escape with stunning views and sunsets. Perched on stilts by Daniel Boone Conservation Area, enjoy tranquility, hiking, and wildlife. Relax in a king-size bed beneath skylights, soak in a tub, or unwind in the hot tub and firepit. Just a mile from the Katy Trail, perfect for cycling or relaxing. Explore Hermann’s wineries, shops, and events. Transportation available from Hermann Trolley, Uber & Lyft. Sleeps 2 adults.

Guest favourite
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, 104 reviews

Country home lower level, private, full kitchen

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 favourite
The living room features high ceilings with a large 75-inch TV mounted above a cozy gas fireplace. Comfortable leather seating arrangements are complemented by decorative elements, including indoor plants and accent pillows. Natural light filters through the windows, enhancing the warm ambiance.
Home in Wentzville
4.98 out of 5 average rating, 118 reviews

Spacious 6BR Oasis | Near I-64 & Weddings

Enjoy a modern smart home near Highway 64, ideal for groups, families, and wedding guests. Enjoy a fully equipped chef’s kitchen, eight 4K smart TVs, high speed WiFi, and a dedicated office for remote work, all enhanced by smart technology for added comfort and convenience. Ideally located with easy access to dining, shopping, and top attractions, and just 30 minutes from STL Airport, this home is designed for a seamless, spacious, and elevated stay.

Guest favourite
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, 150 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 favourite
A townhouse with a two-story facade is depicted, showcasing a front door and multiple windows. A clear concrete pathway leads from the parking area to the entrance. A dedicated parking space marked with the number 5 is visible, highlighting convenience for guests.
Home in St. Peters
4.81 out of 5 average rating, 116 reviews

Family Friendly Townhouse

Your family will be close to everything when you stay at this centrally-located place. Located within walking distance of grocery stores, restaurants, parks, and more. Only a short distance to St. Louis Arch and downtown. This 3 bedroom 2 and a half bath is the perfect place to have all the amenities of the city but far enough away to not have to constantly be in the hustle and bustle of traffic and crowds.

Top guest favourite
A modern studio cabin is elevated on pillars, surrounded by lush greenery. The exterior features dark wood siding and multiple windows, allowing natural light to illuminate the interior. A deck is visible, indicating outdoor space for relaxation.
Farm stay in Grafton
4.96 out of 5 average rating, 338 reviews

Pere Ridge Tree Escape

Welcome to Pere Ridge ! Enjoy the lovely setting of this romantic spot in nature. Pere Ridge is a custom Scandinavian inspired nature escape for two . Our elevated cabin is perched on a ridge with a deck that is surrounded by trees. Our hope is that you disconnect from life's stresses while at Pere Ridge. Our cabin is located in "the ridge " area of Grafton and is a 10 minute drive to Grafton.

Popular amenities for Winfield holiday rentals

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