Holiday rentals in Winfield

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Top-rated holiday rentals in Winfield

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Superhost
A modern studio condo features a king-sized bed with floral bedding, a cozy seating area with plush pillows, and a flat screen TV mounted on the wall. Large sliding glass doors open to a private deck, providing natural light and a view of the surrounding landscape.
Apartment in Wright City
4.8 out of 5 average rating, 10 reviews

Geneva Retreat by Innsbrook Vacations!

Welcome to Geneva Retreat! Simple, yet modern studio condo located on the shores of beautiful 150 acre Lake Aspen and only steps away from Geneva Beach! Vacation in style with this recently updated condo featuring an indoor fireplace, plush furniture, fully equipped kitchen, king-sized bed and sleeper sofa, and a spacious deck perfect for enjoying your morning coffee. Packed with all the essentials, this property is prepped with everything you need to enjoy your stay in comfort. Whether your ideal vacation is cozying up by the fireplace or adventuring on the lake waters, this condo is the perfect fit for you! Located in the heart of Innsbrook, guests can explore all the outstanding amenities Innsbrook has to offer that are only a short car ride away. Experience the Innsbrook lifestyle to the fullest on one of the many beaches by Lake Aspen, play 18 rounds of golf on the championship golf course, or grab a bite to eat at the Clubhouse Bar & Grille that is host to many live music events. To top it off, guests can participate in any of the Innsbrook community events including kids’ camps, adult workshops, painting classes, and much more! Our staff of vacation experts continuously provide outstanding service and specialize in bringing you the best experience possible when it comes to your Innsbrook accommodations, before and during your stay! Discover Innsbrook, and book your stay with Innsbrook Vacations today! Condo Amenities: • 1 king bed and 1 sleeper sofa • Full Bathroom • Fully equipped kitchen with all cooking utensils provided • Indoor fireplace • Private deck • Flat screen TV with streaming capability • WiFi Resort Amenities Include: • Seasonal Boat and Water Equipment Rentals (kayaks, canoes, paddle boards, paddle boats) • Beach Access • Seasonal- Charrette Creek Commons Swimming Pool with Swim Lanes, Lazy River, and Outdoor Concessions. • Seasonal – Tyrol Oasis Pool • Children's Playground • Fitness Center • Outdoor Amphitheater • Clubhouse Bar & Grille (seasonal- hours may vary) • 18-hole Golf Course • Par Bar- Golf Course eatery (seasonal- hours may vary, subject to closure due to inclement weather) • Driving Range and Putting Green • 7 Hiking Trails • Tennis Courts • Pickle Ball Courts • Basketball Courts • The Market Café & Creamery- serving Starbucks branded coffee, breakfast and lunch items, sweet treats and hand-scooped ice cream! Plus, convenient store items, wine and spirits, and Innsbrook merchandise • Giant Outdoor Chess Board • Seasonal Events Including Summer Breeze Concert Series, Kids Camps, Fireworks Show, and Much More! Nearby attractions include Big Joel's Safari and Cedar Lake Winery. Innsbrook Resort is located 45 minutes West of St. Louis.

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
4.94 out of 5 average rating, 101 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 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, 165 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.

Superhost
An open-concept living area features a dark blue couch and a granite-topped coffee table. The kitchen showcases modern appliances and seating for two. A bright bedroom contains a spacious bed, complemented by colorful artwork above it. Large windows provide natural light throughout.
Flat in Central West End
4.83 out of 5 average rating, 104 reviews

Welcoming Downtown West Suite- King w/ Patio (223)

Enjoy your stay in one of our corporate housing retreats! Great housing option for anyone looking to stay in town for short or long-term periods of time! Fully equipped with all of your basic amenities and a few extras! We proudly boast a comfortable and enjoyable stay, all in the heart of PRIME Central West End St Louis! This location is great for anyone who wants to be located close to: - Barnes Jewish Hospital - SLU - Wash U - The Zoo - Nightlife - Downtown festivities and so much more!!

Guest favourite
Cabin in Wright City
4.95 out of 5 average rating, 19 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.

Top guest favourite
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, 83 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 favourite
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 favourite
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, 83 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 favourite
A charming exterior view of the Rue Royale Condominiums features a covered entrance with black railings and outdoor seating. Potted plants add greenery to the space. An American flag is displayed beside the entrance, and a lamppost is visible, providing a welcoming ambiance.
Apartment in Saint Charles
4.93 out of 5 average rating, 167 reviews

Cozy Studio in Beautiful New Town St. Charles

Stay at this cozy studio centrally located in the amazing community of New Town St. Charles. New Town is a large scale new urbanist community built on the edge of suburbia. You never have to leave New Town with its walkability to restaurants, bars, a market, coffee shops, ice cream, food kiosk, canals, lakes, parks and tree lined streets. If you do leave its only a few miles from historic St. Charles Main street, The Streets of St. Charles, and 25 miles to Downtown St. Louis.

Guest favourite
An aerial view captures a riverfront property surrounded by lush greenery. The home features a large deck overlooking the water, with trees lining the shoreline and open grassy areas nearby. A mix of residential structures is visible in the distance, enhancing the serene country setting.
Home in Hardin
4.98 out of 5 average rating, 48 reviews

Riverfront Home in Calhoun County

Enjoy your relaxing experience nestled alongside the Illinois River in this private, riverfront property. You will be able to spend your time Eagle watching, fishing, or observing the barge traffic pass through the Joe Page Bridge. This space allows for the perfect country experience right on the back porch. The home is within walking distance of a public boat ramp and restaurant. For a short drive, you may find more restaurants, bars, grocery stores, and a gas station.

Top guest favourite
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
5 out of 5 average rating, 73 reviews

Cottage on Historic Main St- Low Cleaning Fee

MESSAGE FOR DISCOUNT ON SHORT STAY Enjoy walkable luxury in historic St. Charles! This updated 2BR, 1BA unit is steps from Main Street’s best dining, shopping, nightlife & Ameristar Casino. We focus on providing an affordable option for all. Just 12 mins to STL Airport. Includes fast Wi-Fi, smart TV, keyless entry, free parking, full kitchen & cozy living space. Ideal for couples, business travelers & weekend escapes. Safe, stylish & no car needed!

Superhost
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, 125 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.

Popular amenities for Winfield holiday rentals

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