Best Vacation Homes in Winfield
House
10.0(71 Reviews)
2 Bedrooms
2 Baths
4 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $277/Night
7 Nights - US $1,939
New
House
1 Bedroom
2 Baths
10 Guests
1001.04 ft²
- Parking
View- Air Conditioner
Internet
US $321/Night
7 Nights - US $2,245
US $131/Night
7 Nights - US $915
Apartment
8.6(4 Reviews)
1 Bedroom
1 Bath
2 Guests
1000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $157/Night
7 Nights - US $1,101
House
2 Bedrooms
1 Bath
4 Guests
96.88 ft²
- Parking
- Air Conditioner
- Internet
Child Friendly
US $92/Night
7 Nights - US $643
House
2 Bedrooms
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $181/Night
7 Nights - US $1,266
House
10.0(95 Reviews)
3 Bedrooms
2 Baths
6 Guests
1400 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $162/Night
7 Nights - US $1,135
House
10.0(55 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $351/Night
7 Nights - US $2,459
Winfield Luxury Rentals
House
9.4(24 Reviews)
6 Bedrooms
3 Baths
20 Guests
4500 ft²
Hot Tub- Parking
- Balcony/Terrace
- Kitchen
US $1,027/Night
7 Nights - US $7,189
House
10.0(4 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $693/Night
7 Nights - US $4,852
House
10.0(1 Review)
3 Bedrooms
1 Bath
14 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $652/Night
7 Nights - US $4,562
House
10.0(1 Review)
4 Bedrooms
2 Baths
13 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $568/Night
7 Nights - US $3,979
House
10.0(2 Reviews)
4 Bedrooms
3 Baths
11 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $539/Night
7 Nights - US $3,776
US $500/Night
7 Nights - US $3,497
House
9.8(92 Reviews)
5 Bedrooms
3 Baths
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $484/Night
7 Nights - US $3,387
House
9.6(4 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Balcony/Terrace
- Air Conditioner
- Internet
Pet Friendly
US $230/Night
7 Nights - US $1,609
Winfield Pet Friendly Vacation Rentals
US $159/Night
7 Nights - US $1,113
Apartment
10.0(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $180/Night
7 Nights - US $1,259
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $137/Night
7 Nights - US $959
House
9.4(24 Reviews)
3 Bedrooms
1 Bath
6 Guests
2200 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $268/Night
7 Nights - US $1,879
House
6.8(6 Reviews)
4 Bedrooms
2 Baths
8 Guests
1400 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $286/Night
7 Nights - US $2,005
House
4 Bedrooms
2 Baths
10 Guests
2100 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $547/Night
7 Nights - US $3,830
House
4 Bedrooms
2 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $135/Night
7 Nights - US $946
House
5 Bedrooms
2 Baths
10 Guests
1600 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $135/Night
7 Nights - US $945
Winfield Large Vacation Homes
House
5.6(4 Reviews)
4 Bedrooms
4 Baths
11 Guests
- Air Conditioner
- Pet Friendly
- Child Friendly
Laundry
US $305/Night
7 Nights - US $2,135
House
4 Bedrooms
2 Baths
10 Guests
1600 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $629/Night
7 Nights - US $4,402
House
4 Bedrooms
2 Baths
10 Guests
1600 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $361/Night
7 Nights - US $2,527
House
5 Bedrooms
4 Baths
8 Guests
- Air Conditioner
- Laundry
Bedding/Linens
US $350/Night
7 Nights - US $2,450
House
4 Bedrooms
2 Baths
14 Guests
2100 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $325/Night
7 Nights - US $2,275
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?
To make the most of your stay, consider visiting during the shoulder seasons when this destination offers pleasant weather and fewer crowds, ensuring a more relaxed and enjoyable experience in the local area.
Peak Season Highlights
Summer (June to August)
During the summer months, the region experiences warm weather ideal for outdoor activities and exploring local attractions. This is the busiest time for visitors seeking a lively atmosphere and longer daylight hours.
Average Temperature Daytime: around 80-85°F - Nighttime: around 60-65°F
Fall (September to November)
Autumn brings cooler temperatures and vibrant foliage, making it a popular season for scenic drives and outdoor recreation. The area's natural beauty peaks during this period, attracting many visitors looking for picturesque surroundings.
Average Temperature Daytime: around 65-75°F - Nighttime: around 45-55°F
Off-Season Highlights
Winter (December to February)
The quiet winter months offer a peaceful escape with cooler weather and fewer tourists. This is an ideal time for travelers seeking solitude or cozying up in comfortable vacation rentals without the crowds.
Average Temperature Daytime: around 30-40°F - Nighttime: around 20-30°F
Spring (March to May)
Spring sees mild temperatures and blooming landscapes, perfect for those wishing to enjoy outdoor activities before the summer rush begins. It’s a quieter season, providing a relaxed environment for your stay.
Average Temperature Daytime: around 55-65°F - Nighttime: around 35-45°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 areas perfect for meals al fresco amidst the scenic surroundings.
- Relax in a private patio or deck that offers a tranquil space to unwind outdoors.
- Make use of landscaped gardens that enhance your overall outdoor experience here.
- Take advantage of outdoor grilling stations for preparing delicious barbecues with friends and family.
- Stroll through nearby walking paths or trails that showcase the natural beauty of the region.
- Unwind by a fire pit, ideal for cozy evenings during cooler months or starlit nights.
- Benefit from access to spacious yards or lawns, perfect for outdoor activities and games.
Top Attractions Around Winfield
What attractions are nearby?
In this charming destination, you can enjoy a variety of outdoor activities and explore local parks, providing the perfect opportunity to unwind and experience the natural beauty of the area.
Family Activities
- Winfield Community Park: Enjoy outdoor family activities, picnics, and playground fun in this spacious park nestled within the region.
- Glen Ellyn History Museum: Discover local history through engaging exhibits that offer an educational experience for all ages here in the area.
- Derby Run Golf Course: Spend quality time together on the scenic fairways of this nearby golf course suitable for both beginners and seasoned players.
- Lake Ellyn Park: Relax by the lake with fishing, walking trails, or simply take in the picturesque views during your visit to this popular spot in the region.
Adult Activities
- Winfield Village Museum: Dive into the local history and culture at this engaging museum, offering insights into the area's rich heritage.
- Community Park: Relax or enjoy outdoor activities in a scenic setting perfect for picnics, walking, or simply unwinding amidst nature.
- Nearby Golf Courses: Improve your swing and enjoy a round of golf at premier courses conveniently located near the area.
- Local Dining Experiences: Savor a variety of culinary delights at restaurants that showcase the region's diverse flavors and hospitality.
Other Places to Stay in Winfield, IL
Central Dupage Hospital
Fresenius Medical Care at Central Dupage Hospital
Winfield Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Outdoor Activities: Take advantage of the area's beautiful parks and trails to enjoy outdoor adventures that highlight the natural beauty surrounding your vacation rental in Winfield.
- Plan Your Dining Experiences: Discover local eateries and cafes nearby to savor regional flavors and create memorable dining moments during your stay here.
- Utilize Nearby Amenities: Make the most of community facilities and services in the region to enhance your comfort and convenience throughout your visit.
- Connect with Local Events: Check out community events and seasonal festivals happening during your stay to enrich your experience in this destination.
Transportation Options
- Metra Rail Service: You can access frequent train services connecting to the Chicago metropolitan area, making it a convenient option for exploring the region.
- Local Bus Transit: The local bus network offers reliable transportation within the area and to nearby destinations, ideal for easy travel without a car.
- Car Rentals: Car rental services are available nearby, giving you the flexibility to explore this part of Illinois at your own pace.
- Taxi and Ride-Sharing Services: Taxis and ride-sharing options provide a quick and comfortable way to get around here without the need for personal transportation.
Local Customs Options
- Community Events and Festivals: The area hosts various community events throughout the year that reflect local traditions and provide a warm welcome to visitors.
- Local Dining Etiquette: Dining in this destination often involves a friendly, communal atmosphere where sharing meals is valued and appreciated.
- Religious Observances: Respect for local religious practices and holidays is customary when engaging with residents or participating in cultural activities here.
- Recreational Customs: Outdoor activities like fishing and sports are popular among locals, emphasizing an appreciation for the region’s natural beauty and leisure traditions.
Winfield Vacation Rental Frequently Asked Questions
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:
- Enjoy your stay at the Train Conductor’s Cottage!
- Walking distance to downtown shops, hospital and train station.
- Entire House! Sleeps 6-Cozy, Clean & Well-Stocked
- Glamorous Stay in this 3 BR + 3BA House w/Bar and Home Sauna!
- Cozy 4-bedroom house , 3-full baths in marvelous West Chicago with WiFi, AC,
- The Orchard House/King Bed/Privacy/Walking Trail
- PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!
- Spacious open concept home w/game room + firepit
- Charming 3-bedroom house just minutes from Downtown Wheaton!
- 6 Bedrm/3 Bath Spring Retreat, Hot Tub, Fireplace
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 41 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 Winfield, Illinois?
The cancellation policy varies depending on the individual property owner. You should review the specific listing details or contact the host directly to understand the terms and any applicable fees.
5. Are there any additional fees I should be aware of when booking a rental in this area?
Additional fees such as cleaning charges, service fees, or security deposits are specified within each property listing. It's best to read the listing carefully or reach out to the owner for clarification before booking.
6. How do I know if a vacation rental in this region is available for my travel dates?
Availability is updated regularly on each listing. Use the booking calendar to check if your desired dates are open, or contact the host directly for confirmation.
7. What amenities are typically included in vacation rentals in this destination?
Amenities can vary, but most properties offer essentials like Wi-Fi, parking, and fully equipped kitchens. To confirm specific amenities, review the property details or communicate with the owner prior to booking.
8. Is it safe to stay in vacation rentals around Winfield, Illinois?
Safety measures depend on the individual property and host. Reading reviews and contacting the owner can help ensure a secure and comfortable stay in this area.
Winfield Top Rated Vacation Rentals
Hotel
8.9(144 Reviews)
9 Baths
373.15 ft²
Private Pool- Hot Tub
Breakfast- Parking
US $135/Night
7 Nights - US $945
Hotel
8.6(894 Reviews)
1 Bath
- Breakfast
- Parking
Pool- Kitchen
US $115/Night
7 Nights - US $805
Hotel
8.2(192 Reviews)
2 Baths
279.86 ft²
- Private Pool
- Breakfast
- Parking
- Pool
US $110/Night
7 Nights - US $770
