Holiday rentals in Winfield

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Top-rated holiday rentals in Winfield

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Guest favourite
A cozy living area is highlighted by a plush navy sofa adorned with a yellow accent pillow. A light-colored area rug with stripes lies beneath. The room features a decorative painting of trees and a stained glass window, adding character to the inviting space.
Guest suite in Wheaton
4.92 out of 5 average rating, 201 reviews

✽ Charming Cottage ✽ close to College/Town/Station

Charming and cozy single family home fully renovated in a superb location! This house is walking distance to the Chicago metra rail system and Wheaton College, as well as a 6 minute drive to both downtown Wheaton and downtown Glen Ellyn! Relax and unwind in this darling home that we fell in love with! The health and safety of our guests is important to us. Due to COVID-19 we are taking extra care to professionally disinfect frequently and completely between every reservation UP TO CDC STANDARDS

Top guest favourite
A spacious outdoor area features a circular firepit surrounded by seating and bordered by an ivy-covered garden. Large trees frame the setting, with well-maintained grass and a wooden fence enhancing the private yard atmosphere.
Home in Winfield
4.91 out of 5 average rating, 76 reviews

Spacious open concept home w/ game room + firepit

Relax and play in this treetop garden inspired home with an elevated deck overlooking the beautiful spacious yard with large old trees and lots of green. This large open concept home features an outdoor firepit, deck with a dining table + gas grill. The outdoor space is magical at night with string lights strung over the deck. The space is newly renovated with high end finishes, luxurious appliances + quartz. The lower level has a game room with a foosball table, basketball game + board games.

Guest favourite
A bright living area features a comfortable sofa arranged around a modern coffee table. A work desk is positioned near the window, with natural light spilling in. Artwork adorns the walls, and greenery adds a touch of life to the space, enhancing the welcoming atmosphere.
Flat in West Dundee
4.93 out of 5 average rating, 116 reviews

Charming Riverfront Stay | Heart of Downtown

Welcome to The Riverfronts! Three boutique hotel rooms perfectly situated along the river in downtown West Dundee, offering scenic views and modern comforts. ✔ Riverfront Location: Enjoy the scenic riverwalk just steps away. ✔ Prime Downtown Spot: In the heart of downtown Dundee, minutes from top attractions and dining. ✔ Exclusive Group Booking: Reserve just one or all three units for your entire party. ✔ Outdoor Firepit: Unwind by the firepit, perfect for evening gatherings. ✔ Sleeps 4: Each

Guest favourite
A spacious living room features comfortable seating on a large sofa and two accent chairs. A wooden coffee table centers the arrangement, while a patterned area rug complements the decor. Natural light filters in through large windows, creating a bright and inviting atmosphere.
Home in Wheaton
4.93 out of 5 average rating, 27 reviews

Charming 3BR | Game Room, Coffee Bar, Perf Locatn!

Looking to relax in comfort, engage in family fun, boost your productivity and start your mornings right? Our modern 3BR home is the perfect getaway for a family vacation or business trip! Unwind with a game of air hockey or foosball, cater to your work in a dual workstation office, and caffeine lovers will LOVE our fully stocked coffee bar. Centrally located in Wheaton, IL with easy access to numerous restaurants, grocery stores, attractions, parks and the Metra train to downtown Chicago.

Top guest favourite
A spacious bedroom features a queen bed dressed in crisp white linens, accompanied by decorative pillows. Soft lighting is provided by a bedside lamp, while an accent rug adds warmth to the wood floor. A built-in shelf displays various decorative items.
Guest suite in Saint Charles
5 out of 5 average rating, 301 reviews

Peaceful Private Coach-House in St. Charles

Enjoy our cozy and peaceful Coach-house , private entrance with everything you need for a wonderful stay. Newly renovated and updated throughout. Queen bed with mattress topper, studio area includes Smart TV, water station, Keurig coffee machine and quick-set lock. Even though you are less than a mile from downtown St. Charles and 4 miles to the Geneva train station you have a private area. You may see deer out your window overlooking the pool and tennis. Not suitable for children or pets.

Guest favourite
A spacious living area features a corner sectional sofa with soft cushioning and a cozy throw. Large windows provide natural light and city views. A simple coffee table sits in front, with light-colored carpet underfoot, enhancing the comfortable atmosphere.
Flat in Aurora
4.99 out of 5 average rating, 200 reviews

Penthouse In The Historic Hobbs

Experience luxury and historic charm at the Penthouse in the Historic Hobbs. Built in 1892, and restored in 2023, this new one bedroom corner unit offers a panoramic view of the Aurora skyline. Cook a delicious meal in the fully stocked kitchen. Dine at the bespoke table in the window bay under the iconic onion dome. Relax on the cozy sofa and enjoy a movie on the big screen TV. Rest in the plush king-sized bed. This urban retreat is near coffee, shopping, art and entertainment.

Top guest favourite
A cozy living room is furnished with multiple seating options, including wicker chairs and a plush couch decorated with assorted cushions. A round coffee table sits at the center, accompanied by a basket and a small side table. A softly glowing lamp provides warm light, and an electric fireplace is positioned against the wall.
Guest suite in Wheaton
5 out of 5 average rating, 35 reviews

The Garden Flat

Discover comfort and charm in this fully renovated LL garden flat, 2 blocks from Wheaton College. Walk to downtown Wheaton and the train. This delightful bungalow, tucked away in a peaceful neighborhood, offers a private driveway parking space and lovely fenced backyard with patio. The adorable back porch is the perfect spot to enjoy your morning coffee, unwind with a glass of wine, or curl up with a good book. Everything you need is waiting for you at The Garden Flat in Wheaton.

Top guest favourite
A warm living area is surrounded by natural light from a window adorned with floral curtains. Two spacious sofas are placed opposite each other, with decorative pillows adding color. A dining space is visible through an archway, featuring a wooden table and chairs, creating an inviting gathering space.
Home in Wheaton
4.88 out of 5 average rating, 66 reviews

Little House on the Prairie-Path

Little House on the Prairie Path Cozy, gemütlich, hygge cottage in quiet unincorporated Wheaton, close to Lincoln Marsh, on the Prairie Path. International traveler decorated. This house offers extreme coziness. Very kid and pet friendly. Large back yard with fire pit overlooks pond with ducks, egrets, herons. Close to Central DuPage Hospital, Wheaton College, Metra train to Chicago. Perfect for family gatherings. Kitchen is fully equipped for cooking real meals!

Guest favourite
The living room features a spacious sectional sofa and a round wooden coffee table, surrounded by natural light from large windows. Two accent chairs complement the seating area, while framed artwork adorns the walls, adding a touch of style.
Home in Wheaton
5 out of 5 average rating, 11 reviews

Hazelton's Wheaton Gem | Walk2 Starbucks & Target

Try this… UPDATE: Per city ordinance, 30+ day reservations only. Questions welcome—apologies for any inconvenience. Your family will be close to all amenities at this centrally-located, fully renovated retreat just minutes from Downtown Wheaton. Near restaurants, public transport, shopping, and entertainment—perfect for Wheaton College visits or a relaxing suburban escape. Enjoy the beautiful backyard and deck for outdoor lounging & dining. A true gem in Wheaton!

Guest favourite
Flat in Warrenville
4.84 out of 5 average rating, 19 reviews

Modern 4BR Townhouse with Parking & Lake Views

Unwind in this modern 4-bedroom townhouse in Warrenville, designed to comfortably host up to 10 guests. With generous living spaces, a lake view patio, and private parking, it’s perfect for families, groups, or business travelers who want both space and convenience. The open-concept layout brings everyone together—cook meals in the fully stocked kitchen, gather in the living room for movie nights, or step outside to enjoy the peaceful lake view.

Guest favourite
The living area features a comfortable seating arrangement with a sofa and two armchairs. A round coffee table sits in the center on a patterned area rug. Soft lighting enhances the neutral wall tones, while a decorative plant adds a touch of greenery.
Flat in Warrenville
4.92 out of 5 average rating, 91 reviews

“The remote retreat”

We have a cozy one bedroom apartment that is available on the top floor of the home and has its own independent and separate entrance! Comes with free parking on premises; recently renovated; neighborhood is safe and quiet. Shopping center with grocery store, laundry mat and restaurant is available within walking distance! We are only 5 minutes from the expressway I-88 and 10 minutes from Naperville and the outlet mall in Aurora!

Top guest favourite
A welcoming living room is highlighted by a comfortable sectional sofa with decorative pillows. A patterned area rug covers the hardwood floor, and a reading nook features a unique egg chair. Artwork adorns the walls, complemented by greenery from potted plants.
Home in Lombard
4.99 out of 5 average rating, 127 reviews

Modern Boho house in Lombard 7 min to Metra

Kick back and relax in this calm, stylish space. Visiting family in Chicagoland area? Traveling for work? Lombard is centrally located 30 min to everywhere! The house is only 6 min to Oakbrook Shopping and Business Center and upscale shopping and fabulous restaurants like RH with rooftop restaurant, 8 min to Yorktown Shopping Center. Whatever your travel purpose is, we will be happy to host you! Welcome home!

Popular amenities for Winfield holiday rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. DuPage County
  5. Winfield