Best Vacation Homes in Winfield
2100 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
CA $318/Night
For 7 Nights CA $2,228
1097.92 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Hot Tub
- Fireplace/Heating
- Parking
CA $285/Night
For 7 Nights CA $1,997
CA $125/Night
For 7 Nights CA $876
1100 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $301/Night
For 7 Nights CA $2,110
355.21 ft²
4 Bathrooms
Free Cancellation
Hotel
- Parking
- Air Conditioner
- Internet
CA $123/Night
For 7 Nights CA $860
1000 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $248/Night
For 7 Nights CA $1,738
1400 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $362/Night
For 7 Nights CA $2,536
1100 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
CA $310/Night
For 7 Nights CA $2,168
Winfield Luxury Rentals
3200 ft²
16 Guests
6 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
CA $1,484/Night
For 7 Nights CA $10,387
12 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
CA $952/Night
For 7 Nights CA $6,664
10 Guests
8 Bedrooms
8 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $797/Night
For 7 Nights CA $5,583
2536 ft²
10 Guests
8 Bedrooms
8 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $704/Night
For 7 Nights CA $4,928
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $480/Night
For 7 Nights CA $3,363
3800 ft²
8 Guests
3 Bedrooms
4 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $480/Night
For 7 Nights CA $3,358
2000 ft²
7 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $434/Night
For 7 Nights CA $3,037
1600 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $416/Night
For 7 Nights CA $2,910
Winfield Pet Friendly Vacation Rentals
945 ft²
6 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $221/Night
For 7 Nights CA $1,548
CA $98/Night
For 7 Nights CA $688
1500 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $375/Night
For 7 Nights CA $2,624
1700 ft²
7 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $411/Night
For 7 Nights CA $2,878
1900 ft²
4 Guests
2 Bedrooms
3 Bathrooms
Couples Retreat
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
CA $276/Night
For 7 Nights CA $1,934
6 Guests
1 Bedroom
1 Bathroom
Family Friendly
RV Rental
- Pet Friendly
- Child Friendly
- Security/Safety
CA $79/Night
For 7 Nights CA $550
1500 ft²
7 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Pool
- Ocean View
CA $217/Night
For 7 Nights CA $1,519
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Pet Friendly
- Air Conditioner
- Internet
CA $478/Night
For 7 Nights CA $3,347
Winfield Large Vacation Homes
16 Guests
8 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Kitchen
- Parking
CA $579/Night
For 7 Nights CA $4,050
13 Guests
1 Bedroom
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $528/Night
For 7 Nights CA $3,695
16 Guests
8 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Air Conditioner
- Internet
CA $154/Night
For 7 Nights CA $1,076
16 Guests
8 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
CA $154/Night
For 7 Nights CA $1,076
Why Choose Rent By Owner for your Winfield Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Winfield
When should you plan your Vacation Rentals stay?
Choosing the optimal time to vacation in this region can enhance your experience, allowing you to enjoy the local climate and seasonal events while making the most of your stay in Winfield, Missouri.
Peak Season Highlights
Spring (March to May)
During spring, the region experiences mild temperatures and lush scenery, making it an ideal time for outdoor activities and exploring this destination’s natural beauty.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Summer (June to August)
Summer brings warm weather and longer days, perfect for enjoying the area's outdoor attractions and relaxing in your chosen vacation rentals.
Average Temperature Daytime: 85°F to 90°F - Nighttime: 65°F to 70°F
Off-Season Highlights
Fall (September to November)
In fall, the weather cools down, offering a more serene environment for those seeking quieter times to enjoy this destination's peaceful atmosphere.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
Winter (December to February)
Winter months tend to be cooler, providing a cozy setting for visitors interested in experiencing a quieter and less crowded period here.
Average Temperature Daytime: 40°F to 50°F - Nighttime: 25°F to 35°F
Weekly Weather Forecast for Winfield
How to Book Your Winfield Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Winfield
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining on a private patio or deck to make the most of the area's pleasant weather.
- Relax by a welcoming outdoor fireplace or fire pit during cooler evenings in this destination.
- Take advantage of spacious lawns or gardens perfect for outdoor games and activities.
- Make use of a boat dock or access to nearby waterway for fishing, kayaking, or boating adventures.
- Benefit from scenic balconies or verandas that offer picturesque views of the region’s natural beauty.
- Utilize outdoor grills to prepare delicious meals while soaking in the serene surroundings.
- Explore well-maintained walking trails or nature paths accessible directly from your rental here.
Top Attractions Around Winfield
What attractions are nearby?
Nearby, you can explore a variety of outdoor activities in the region, including scenic parks and nature trails that provide perfect opportunities for relaxation and adventure during your stay.
Family Activities
- Winfield City Park: Enjoy a relaxing day outdoors with family-friendly playgrounds, walking trails, and picnic areas in this popular local park.
- The Winfield Historical Museum: Discover the area's rich history through engaging exhibits and artifacts that educate and entertain visitors of all ages.
- Local Nature Trails: Explore scenic hiking and biking trails around the region that are perfect for active families seeking outdoor adventure.
- Family-Friendly Events: Attend seasonal festivals and community gatherings hosted here, offering entertainment and activities suitable for children and adults alike.
Adult Activities
- Exploring the Winfield City Park: Enjoy a relaxing day outdoors at this scenic park, perfect for picnicking, walking, or simply unwinding amidst natural beauty.
- Visiting local antique shops and boutiques: Discover unique finds and charming souvenirs in the quaint shopping areas that reflect the area's rich history and community spirit.
- Golfing at nearby courses: Experience a round of golf on well-maintained courses that cater to all skill levels, offering a chance to enjoy the region's pleasant weather.
- Attending community events and festivals: Immerse yourself in local culture by participating in seasonal events, farmers' markets, and festivals hosted throughout the year here.
Other Places to Stay in Winfield, MO
Monroe Township
Winfield Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Outdoor Activities: Take advantage of the area's natural beauty by enjoying outdoor pursuits like fishing, hiking, or boating, which showcase the region's scenic landscapes.
- Discover Nearby Dining Options: Savor regional flavors at local eateries that highlight the culinary traditions unique to this destination, making your stay more memorable.
- Plan Your Visit During Peak Seasons: Opt for travel during the area's most beautiful seasons to experience the region’s vibrant ambiance and outdoor attractions at their best.
- Utilize Trusted Vacation Rentals: Book through reputable vacation rentals that offer comfort and reliability, ensuring a seamless stay in this inviting destination.
Transportation Options
- Winfield Transit Bus Service: Offers convenient local bus routes to help you navigate the area easily during your stay.
- St. Louis Lambert International Airport: The primary airport serving the region, providing domestic and international flights within a short drive from here.
- Rental Car Services: Several rental companies are available nearby, allowing you to explore the region at your own pace with flexibility.
- Taxi and Rideshare Options: Reliable taxi services and rideshare apps like Uber and Lyft are readily accessible for quick trips within and around the destination.
Local Customs Options
- Local Dining Etiquette: When visiting eateries here, it's customary to greet staff warmly and wait patiently during busy hours, reflecting the area's friendly community spirit.
- Community Events: Participating in local festivals and gatherings is a valued tradition, offering you an authentic way to connect with residents in this welcoming region.
- Respect for Nature: The residents cherish outdoor spaces, so it's important to follow trail guidelines and dispose of waste properly when enjoying the area's natural beauty.
- Historical Preservation: Preserving the region's history is significant, so be mindful to respect historical sites and adhere to any visitor guidelines during your stay.
Frequently Asked Questions About Winfield?
1. What are the top vacation rentals in Winfield?
There are a lot of options in Winfield. If you plan on staying in the Winfield area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Winfield:
- Escape the city to quiet and picturesque Golden Eagle, IL.
- Welcome to the "Blue House on Boone"
- Historic Main Street Cottage
- Relaxing, Quiet get away where you can enjoy the outdoors.
- The Chicken Coop on Highway H
- The Hidden Gem - 2BR Basement Apartment on 7 Acres
- 'Foxes Den' w/Hot Tub, Pool Table & Fire Pit!
- Hill Manor at the Crossroads of the Nation
- Foxes Den with Hot Tub, Pool Table and Fire Pit!
- Groovy In-Laws Suite
2. Which vacation homes in Winfield are best for families?
If you are looking for a family-friendly vacation home in Winfield, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Winfield:
3. How many Rentbyowner vacation rentals are available in Winfield?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 36 in the Winfield area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Winfield.
4. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary by listing, so you should review the specific rental details and contact the property owner if you have any questions about cancellations or refunds.
5. How do I check if my preferred dates are available for booking?
Availability depends on the individual property listing. You can view real-time availability on the booking platform or reach out to the host directly for confirmation.
6. Are there any specific house rules I should be aware of when staying in a vacation rental here?
Each rental has its own set of house rules listed on the property page. It’s recommended to read these rules carefully before booking and communicate with the host if you have any special requirements.
7. What amenities are typically included in vacation rentals in this destination?
Amenities vary by property but often include essentials like Wi-Fi, parking, and fully equipped kitchens. Check the individual listing details for a comprehensive list of what's included.
8. How do I contact the property owner or manager if I need assistance during my stay?
Contact information is provided on the booking platform or within your reservation details. Reach out through the platform’s messaging system for prompt assistance.
