Winfield vacation rentals

We found 328 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Winfield that are perfect for your trip. Whether you're traveling with your kids or with friends, vacation rentals have the best amenities for hanging out with the people that matter most, which might include air conditioning and a pool. No matter what you're looking for, you'll be able to choose a rental that has what everyone needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Winfield

Showing deals for:Nov 7 - Nov 14
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Find out more about Winfield

Find out more about Winfield

Why visit Winfield

  1. Outdoor Adventures: Winfield is perfect for nature lovers, offering numerous parks and scenic spots for relaxation and family fun.
  2. Charming Suburban Atmosphere: Experience the inviting suburban charm that makes Winfield an ideal vacation destination.
  3. Local Events: Attend various events at local conference venues, providing entertainment and networking opportunities.
  4. Proximity to Vibrant Cities: Explore nearby Naperville for a lively atmosphere and friendly community.
  5. Diverse Accommodation Options: Choose from cozy apartments, spacious homes, or stylish condos for a perfect home away from home.

Popular types of accommodation in Winfield

If you're looking for the perfect getaway in Winfield, you'll find a variety of fantastic vacation rental options. Our most popular accommodations include cozy apartments, charming houses, and modern condos. Whether you're searching for apartments in Winfield, homes to rent, or stunning view apartments, we have everything you need to make your stay unforgettable. Explore your options and discover the ideal place to relax and unwind in this delightful destination.

  • Apartments: The top choice for vacation rentals in Winfield, offering comfortable living spaces ideal for solo travelers or families.
  • Houses: A popular option for those seeking a home-like atmosphere, perfect for groups or families wanting privacy.
  • Condos: A favored alternative, providing modern amenities and a community feel for vacationers.
  • Cottages: Quaint and charming, these rentals provide a cozy retreat amidst nature.
  • Caravan Parks: A unique option for adventurous travelers looking to enjoy outdoor living and community vibes.**

Top attractions in Winfield

Winfield, Illinois, is an ideal destination for outdoor enthusiasts, families, and business travelers alike. Visitors can enjoy urban parks, attend events at conference venues, and explore modern colleges and universities. With a variety of attractions catering to outdoor adventures and cultural experiences, Winfield offers something for everyone, making it a perfect spot for a memorable vacation.

  1. Wheaton College: This historic college offers a charming campus with beautiful architecture and a vibrant cultural atmosphere. It's a great place to explore the rich history and enjoy the scenic surroundings.
  2. Morton Arboretum: A stunning outdoor space perfect for families, Morton Arboretum features diverse plant collections and beautiful trails. Enjoy picnicking, hiking, and nature programs in this peaceful environment.
  3. College of Dupage: A modern college with a lively city vibe, it offers various cultural events and art exhibits. The campus is designed for community engagement and learning.

Things to do recommended for couples

For a romantic getaway in Winfield, consider dining at Schaumburg Medieval Times for a unique experience. Enjoy wine tasting at Lynfred Winery, or unwind together with a soothing treatment at Heavenly Massage. Each spot offers a perfect blend of romance and local charm!

Things to do recommended for families

Families visiting Winfield can enjoy a relaxing day at Cantigny Park, just 0.6 miles away, or take a dip and have fun at Centennial Beach, 6 miles from town. For sports enthusiasts, the Allstate Arena offers exciting events, located 17 miles away.

Things to do recommended for groups

In Winfield, groups can enjoy shopping at the Chicago Premium Outlets only 7 miles away, catch a show at the charming Arcada Theater 9 miles off, or play a round of golf at the scenic Cantigny Golf Club just 1 mile from town, embracing outdoor sports and entertainment.

What do I need to keep in mind when booking a vacation in Winfield

If you're planning a trip with a group, family, or pets, or if you're interested in longer stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Winfield with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily apply filters for all these options and more on Vrbo.
  • Traveling to Winfield with young kids: Traveling with young kids can be demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Winfield: For many families, a vacation wouldn’t feel complete without their furry companion. If that resonates with you, take a look at Vrbo listings that welcome pets. Many of these pet-friendly properties offer feeding bowls and beds, ensuring that your entire family feels comfortable and at home.
  • Planning for a long term stay visiting Winfield: If you’re in search of vacation rentals that offer discounts for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Winfield

Winfield, Illinois, offers a delightful blend of suburban charm and outdoor activities, perfect for family vacations or business trips. Explore the nearby cities, such as Naperville, known for its vibrant atmosphere and friendly people. Enjoy local parks and scenic spots, making it ideal for relaxation and family fun. Whether you're seeking romance or urban experiences, Winfield serves as a gateway to memorable adventures in the heart of the Midwest.

  • Schaumburg: Located 13 miles from Winfield, Schaumburg is a vibrant city that offers an exciting blend of family-friendly activities and business opportunities. Known for its expansive Woodfield Mall, one of the largest shopping centers in the United States, visitors can enjoy a diverse array of retail outlets, restaurants, and entertainment options. The city is also home to the Schaumburg Boomers Stadium, where sports enthusiasts can catch a minor league baseball game. With its convention center and various theaters, Schaumburg is an ideal destination for both leisure and business travelers looking to experience urban excitement.
  • Willowbrook: Also 13 miles from Winfield, Willowbrook is a charming suburb that invites visitors to explore its beautiful parks and family-friendly atmosphere. The city features a variety of shopping areas and theaters, making it a convenient spot to unwind after a day of adventure. Outdoor enthusiasts can enjoy the scenic trails and green spaces within local parks, which provide a perfect backdrop for picnics and recreational activities. With its welcoming environment and access to sports facilities, Willowbrook is a great place for families and nature lovers alike.
  • Rosemont: Situated 17 miles from Winfield, Rosemont is a dynamic city known for its sports venues and business facilities. The area is home to the Allstate Arena, where you can catch exciting events, from concerts to sporting matches. Rosemont's entertainment district includes shopping centers and theaters, providing a variety of options for dining and leisure. Additionally, the city hosts many conventions and events at its modern conference venues, making it a hub for both tourists and business travelers seeking a lively experience.

Best time to go to Winfield

If you're planning a trip to Winfield, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and June to July, while off-peak times, like October and December to January tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January23.5°F (-4.7°C)Light RainMostly CloudyModerately LowSlightly Low
February25.7°F (-3.5°C)Light RainMostly CloudyAverageSlightly Low
March38.3°F (3.5°C)Light RainMostly CloudyAverageAverage
April48.2°F (9.0°C)Light RainMostly CloudyModerately HighSlightly Low
May60.3°F (15.7°C)Light RainMostly SunnyAverageSlightly High
June70.0°F (21.1°C)Light RainMostly SunnyModerately HighSlightly High
July74.1°F (23.4°C)Light RainMostly SunnyModerately HighAverage
August73.0°F (22.8°C)Light RainMostly SunnyAverageSlightly High
September66.6°F (19.2°C)Light RainMostly SunnyAverageAverage
October54.0°F (12.2°C)Light RainMostly SunnyModerately LowAverage
November40.8°F (4.9°C)Light RainMostly SunnyAverageAverage
December31.3°F (-0.4°C)Light RainMostly CloudyModerately LowAverage

Booking with Vrbo is simple

Are you eager to save on your upcoming travel adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking for a longer duration to enjoy substantial savings. To discover a Vrbo property that aligns with your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your booking. Being the planner has its perks! When you join our travel rewards program, One Key, you can immediately access member discounts and earn OneKeyCash™ on eligible reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides an organized platform for you to plan new journeys, manage your existing arrangements, and review your reservations. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

Book a vacation rental for your Winfield getaway

Learn about the unique charm of Winfield with a stay in a private vacation home. This city is well-known for its shopping and restaurants. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Sightseeing in and around Winfield

Are you looking for attractions to visit in the city? Venture out of your vacation home and experience everything that Winfield has to offer. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Cantigny Golf Club (1 mi / 1.7 km)
  • Seven Bridges Golf Club (7.7 mi / 12.5 km)
  • Villa Olivia Country Club (10.9 mi / 17.5 km)
  • Oak Brook Golf Course (12 mi / 19.3 km)
  • Pirates Cove Childrens Theme Park (12.3 mi / 19.8 km)
  • Rainbow Falls Waterpark (13.2 mi / 21.2 km)

Exploring the natural features in Winfield

Whether you're an outdoor enthusiast or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Winfield. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Centennial Beach (6.3 mi / 10.1 km)
  • Riverwalk Park (6.4 mi / 10.2 km)
  • Morton Arboretum (6.5 mi / 10.5 km)
  • Fabyan Villa Museum & Japanese Garden (7.8 mi / 12.5 km)
  • Elgin Sports Complex (13.1 mi / 21 km)
  • Lake Park (17.1 mi / 27.6 km)

Transportation to and around Winfield

Fly into Chicago, IL (DPA-Dupage), the closest airport, located 5.8 mi (9.3 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Chicago O'Hare Intl. Airport (ORD), which is 15.4 mi (24.8 km) away.

If you prefer train travel, you can make your way to Winfield Station.

Frequently asked questions

How much does it cost to rent a vacation rental in Winfield?
The average price for a vacation rental in Winfield depends on a number of factors, including season, property type and length of stay. Whether you're searching for a sprawling villa with space for extended family or a cozy cottage ideal for just you and the kids, just enter your dates of travel to find stays with exceptional value.
How much does it cost to rent a beach house in Winfield?
The average price for a vacation rental by the beach in Winfield depends on when you're visiting the area and the size and type of property you're searching for. You can find prices quickly and easily on Vrbo by entering the dates you'll be traveling. Then use the filter tool to select the number of bedrooms and amenities important to you, like WiFi, air conditioning and a hot tub.
Are there pet-friendly vacation rentals in Winfield?
Yes, there are. You can pick from two vacation rentals that cater to pets in Winfield. Some of our pet-friendly vacation rentals come with space outdoors for your furry friend to play around in, complimentary treats, doggie beds and proximity to parks or green space. Apply the "Pets allowed" filter to find a pad that'll get tails wagging on Vrbo.
What are popular rental amenities in Winfield?
The most popular rental amenities people are looking for in Winfield include a garden, a barbecue grill and a fireplace. Whether you're on the road with family, your besties or even pets, Vrbo vacation homes provide the best amenities for chilling out with the people that matter most.
Are there large group vacation rentals in Winfield?
Take your pick of two Vrbo vacation rentals in Winfield that can sleep five or more people. You'll get all the privacy and space you need to kick back with your nearest and dearest — and nobody else.
Are there vacation rentals in Winfield that welcome kids?
Winfield has two family-friendly vacation rentals. And finding a stay that welcomes children is super easy with Vrbo's "Properties good for families" filter. Besides having the entire place to yourselves, you'll also enjoy access to conveniences and perks like living rooms, yards and private pools.
What are the top attractions for families in Winfield?
Spend a day out with the kids at Royal Golf Club at Klein Creek. This leading attraction is within easy reach of the heart of Winfield.
Are there vacation rentals with WiFi in Winfield?
Whether you'd like to keep up to date with the news, look over emails or surf social media, there are two vacation homes with WiFi in Winfield. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Winfield?
You can pick from two vacation homes with air conditioning in Winfield offering that cooling breeze and extra bit of comfort. Enter your dates of travel and then make use of our filters to help you book properties with air conditioning.
How old do you have to be to rent a vacation rental in Winfield?
The minimum age requirements can differ across properties on Vrbo, so be sure to check the rules of the vacation home in Winfield you're considering. But normally, it's 16, 18 or 21.
How long can I rent a vacation rental in Winfield for?
The amount of time you can rent a Winfield vacation rental for depends on each property. Simply tap in your dates of travel to browse options offering extended stays. They feature all the things you need to make your extended trip more convenient and enjoyable, such as air conditioning and kitchens. Some vacation homes might also offer weekly or monthly discounts, so you can stay longer for less money.
Does Vrbo offer discounts for vacation homes in Winfield?
In Winfield, you'll find great discounts and bargains for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you're after a mini vacay or a much longer stay, we have a variety of options to suit your style.

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