Vacation rentals in Winfield

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Top-rated vacation rentals in Winfield

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Guest suite in Carol Stream
4.95 out of 5 average rating, 329 reviews

Lakefront Hot Tub-Fishing-Kayak & Pool Table Suite

Very large guest suite w/3 separate areas. Just like your own apartment, just not your own entrance. Great for friends traveling together! ENTRANCE IS THRU THE MAIN PART OF THE HOUSE. This is just for the basement but you have complete privacy down there. Fenced-in yard, hot tub, patio, bbq, firepit, enjoy fishing or sitting watching the sunsets. Stocked lake, walking path, 3 parks! Check out the pictures to see all our home has to offer! Full kitchen,laundry room & yard are shared space

Superhost
A living area is highlighted by a large mural depicting a misty forest. An earthy-toned armchair sits beside a green sectional sofa, while a wooden coffee table holds decorative plants and water bottles. Natural light filters through sheer curtains, enhancing the serene atmosphere.
Apartment in Geneva
4.81 out of 5 average rating, 132 reviews

Immaculate*1MiTrain*1GWifi*King*ParkFree*FullKitch

2BR/1BA Garden unit. 1 mi to 3rd st. Hotel Baker 3mi, Equestrian Center 9mi, walk to Fox River Bike Trail, bars. Metra (1 mi), restaurants, golf, shopping. New cookware, Keurig, kitchen appliances, French press, rice cooker, Insta pot, blender. Bike path 3 blks. External cameras at door/public coin laundry area. Unit contains a smoke detector, motion sensor, decibel monitoring. Guests under 25+ yrs require owner approval. Price includes 2 guests-$20/night/guest after 2 occupants.

Guest favorite
A treehouse elevated above ground showcases a wooden exterior with a balcony. An inviting staircase leads to the entrance, surrounded by lush greenery and vibrant leaves creating a natural setting. The sturdy structure is supported by wooden beams, blending harmoniously with the surrounding trees.
Treehouse in Schaumburg
4.94 out of 5 average rating, 868 reviews

Enchanted Garden Treehouse (Amenity*)

Summer's here, the treehouse air conditioned and cozy, and the hot tub ready! Relax in our luxurious, 420 friendly, very private, 4' deep cedar hot tub nestled in the evergreens, while the moon and stars swirl overhead, the waterfall tumbles into the koi pond, and the fire table and torches blaze. The stream makes this a wildlife refuge, with many birds, squirrels, rabbit & fox. Come experience the magic and make a special memory! See why Chgo Magazine rates us top 3 staycations in Chgo!

Top guest favorite
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.
Apartment in Aurora
4.98 out of 5 average rating, 257 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 favorite
Loft in West Dundee
4.96 out of 5 average rating, 321 reviews

124 Lofts #4 - Downtown Dundee - Walk to Dining

124 Lofts is a boutique collection of modern, design-forward lofts set within a beautifully restored historic building in downtown West Dundee. This listing is for Loft #4, a one-bedroom space featuring exposed brick, warm textures, and a comfortable layout that blends industrial character with a relaxed, inviting feel. Each loft includes a king bed, private bath, kitchenette, fast Wi-Fi, and a 60" smart TV, just steps from restaurants, shops, and the Fox River.

Guest favorite
A cozy bedroom features a black metal bed frame adorned with soft pillows in pink and green hues. Textured white bedding is spread across the bed. Natural light filters through the large windows, complemented by light-colored curtains, and a nightstand sits beside the bed.
Guesthouse in Lake Forest
4.81 out of 5 average rating, 120 reviews

Designer's Dream in the North Shore!

Welcome to the newly designed cottage at Longmeadow. A tranquil escape from the city hustle of Downtown Chicago. Enjoy the serene setting while close proximity to town amenities, public transit and beautiful trails and parks. A cozy retreat in the wintertime to snuggle up with a great book and hot cocoa. It's also a perfect summer cottage for adventurers looking to take advantage of the beautiful landscape ! Check us out on: Instagram! longmeadowcottage

Top guest favorite
The exterior of the vintage garage apartment is shown, featuring a bright yellow facade with two white garage doors. A large window is positioned above the doors, with greenery surrounding the property, contributing to the charming appearance.
Guesthouse in Villa Park
4.93 out of 5 average rating, 156 reviews

Eclectic Coach House Apartment

Vintage Charmer! 1935 Sears Craftsman Coach House garage apartment. Beautiful safe neighborhood surrounded by historic homes and just steps from the Illinois prairie path, parks, brewery's/bars, restaurants and more! With an eclectic boho chic vibe, featuring full kitchen and on site private washer/dryer. Overlooking an accessible lovely backyard! Close to airports and easy access to public transportation/major highways. Just 30 min from the Chicago Loop!

Guest favorite
The exterior of the Victorian Sherwood House showcases its distinct pink siding accented with green trim. Stained glass windows add character, and multiple gabled roofs enhance its architectural design. A canopy of trees provides a natural backdrop to this charming residence.
Apartment in Elgin
4.8 out of 5 average rating, 201 reviews

Sherwood House

Enjoy the ambience of the Sherwood House, an 1884 Victorian built for Judge David Sherwood. Use of entire first floor apartment including a full kitchen is perfect for longer term stays. Original features include multiple stained glass windows, beautiful wood work, multiple decorative fireplaces and hardwood floors. Located just blocks from downtown Elgin, walk to shops, restaurants, the casino, bike trail or Metra. WiFi and off street parking.

Top guest favorite
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.
Apartment in Warrenville
4.93 out of 5 average rating, 114 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 favorite
The exterior of the Coach House features white siding and a covered entry, framed by greenery. Two doors are visible, leading into the house, while a decorative wall piece is positioned above the entrance. A pathway lined with plants guides the way to the front steps.
Guesthouse in Batavia
4.92 out of 5 average rating, 326 reviews

Quaint Batavia Coach House

The Coach House is located behind our house. It is a private and separate little house. It is located close to the river path and lots of restaurants. The upstairs is one big room that has 1 queen and 2 twin beds. The upstairs also has a full bath. The TV in main living area on first floor is not hooked up to cable, but you can log into all of your apps and have access to news via YouTube TV, Netflix, Prime etc.

Guest favorite
A spacious living area features two comfortable leather sofas and a wooden coffee table. A dining area with a small table and four chairs is visible, along with a bookshelf displaying various items. Soft lighting and neutral walls contribute to an inviting ambiance.
Guest suite in Wheaton
4.87 out of 5 average rating, 130 reviews

Guest Suite by Wheaton College

Come and enjoy visiting your Wheaton College student while staying a short walk from campus. Our apartment has two bedrooms, a well-equipped kitchenette, laundry, bathroom, and living room. The apartment is in the basement our family home with a private entrance and both bedrooms have large windows with lots of natural light. This apartment is not equipped or suitable for children.

Top guest favorite
A log home is set against a bright sky, featuring a spacious covered porch with wooden railing and several potted plants. Large windows flank the entrance, while natural stone accents the chimney. A grassy area surrounds the home, enhancing its tranquil ambiance.
Home in Geneva
4.94 out of 5 average rating, 126 reviews

New Modern Log Home Retreat in the Heart of Geneva

Located minutes from bustling downtown Geneva, this authentic log home is nestled on a quiet residential street on a nature filled half acre. Built in 2007, this home will be yours to use as a homebase for downtime or as you explore the many sights, eateries, and shopping of Geneva and the surrounding area.

Popular amenities for Winfield vacation rentals

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