Vacation rentals in Winfield

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.

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!

Spacious & Quaint Home | Game Room | LOTS of Beds!

Our 4bd, 2ba house is perfect for a group of friends or family looking for a clean, spacious, yet quaint place in a wonderful neighborhood. There is plenty of space for 13 people to sleep comfortably (8 beds + additional couches/futons), as well as 4 smart TVs, a deck AND a balcony, a gas grill, a firepit, a large backyard w/ patio seating, a game room (w/ ping pong and more), a workspace, & much more. Great access to nearby suburbs and to the City of Chicago by major roads and highways!

Cozy Family Getaway

Visit West Chicago with your whole family in this newly renovated home. Toys, books, and games will keep the little ones occupied. Or relax in front of the fireplace and watch a movie (TV has Disney+). Outdoor amenities include an EV charger (free for guests), fenced backyard, 3 parking spaces, deck, and grill. We are within walking distance to the Metra train station, coffee shops, and restaurants. Comfortably fits four, but can accommodate up to six with the floor mattress.

The Train Conductor's Cottage

Enjoy your stay at the Train Conductor’s Cottage! Welcome to our charming home in a family neighborhood, just a couple of blocks away from the Metra train to Chicago & from West Chicago's authentic Mexican restaurants. We are close to Wheaton College, North Central College, Dupage Airport, and Central Dupage Hospital. Rest and relax in a queen bed, full bed, two twin beds, two full bathrooms, spacious children's play area. Amazon Fire stick, WiFi, TV. “All aboard!”

Little House on the Prairiepath by Wheaton College

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!

“The Warrenville Grove”

This bright 2-bedroom home is designed for comfort, with a modern living space, fully equipped kitchen, washer & dryer and a cozy yard to unwind in. Perfect for small groups or families, you’ll be close to local dining, parks, and just a short drive from Naperville and downtown Chicago. We are less than a mile away from the expressway I-88. Whether you’re here for work or leisure, this spot makes it easy to relax, recharge, and explore.

“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!

The Tailor's Loft, 1 bdrm apt. in Downtown Geneva

The Tailor's Loft is located right the the heart of historic downtown Geneva and is walkable to dozens of unique restaurants and shops. This apartment has been completely renovated in a fresh modern style. It is a great space for a couples getaway, girls weekend or extended stays. High ceilings and open floorpan with separate king-size bedroom. In unit washer/ dryer. Easy walk to the Geneva train station (0.5 miles).

Cozy Lakeview Studio with Private Access

Enjoy luxury and comfort in this cozy lakefront studio with a private entrance, attached to a home where the friendly hosts reside. The studio offers a plush queen bed, a kitchenette with a mini fridge, microwave, induction cooktop, and a full bathroom. Located in one of Naperville’s safest neighborhoods, it’s just moments from cafes, restaurants, markets, and a biking trail, with easy access to I-88.

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.

Glamorous: Sauna & Bar

Step into your stylish escape at this beautifully updated ranch, where every detail has been designed for a truly glamorous experience. From the fully renovated kitchen to the dreamy indoor sauna, or the modern bar, this home offers a blend of upscale comfort and fun that’s perfect for your next getaway.