Vacation rentals in Winfield

Lake Home Retreat! HotTub• FirePit• Kayak• Fishing

Come enjoy our beautiful home it's the perfect place to relax, unwind & enjoy peaceful lake views. Whether you’re fishing, soaking in the hot tub or sipping coffee on the deck, it’s a quiet home away from home on a serene cul-de-sac. Enjoy stunning views of the lake while grilling or relaxing by the firepit on the beautifully landscaped patio & in the hot tub 🥂 🐶 Up to 2 furry babies are welcome & they’ll love the almost 1-acre fenced yard! 🌅 See weekly & monthly discounts for longer stays

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/cool 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!

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

Welcome to the Naperville Nest! Rare North Naperville opportunity to find a home suited for the whole family! Pets are more than welcome to enjoy the 1/2 acre fully fenced in yard. This is a a fully updated home minutes from Downtown Naperville, I-88 and many more exciting destinations in the Western Suburbs. You will feel at home whether you're inside or outside...each bedroom has it's own TV and the outdoor living includes natural gas firepit & grill/dining table...this home has it all!

Industrial Loft Above the Brewery

Experience luxury and historic charm at this Industrial Loft. Built in 1929, and restored in 2025, this brand new, top-floor, one bedroom unit offers a Juliet balcony with a view of the Downtown Aurora skyline and Fox River. Located directly above the new Foreign Exchange Brewing Company, it's the perfect spot for beer lovers to unwind with a pint and dinner. Enjoy a beer at the balcony. Relax on the cozy sofa and enjoy a movie on the 75" screen TV. Rest in the plush king-sized bed.

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!

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!

Sunny Garden Unit Efficiency Studio in Wheaton

Enjoy a cozy getaway in our sunny basement studio, conveniently situated near downtown Wheaton, downtown Glen Ellyn, Wheaton College, College of Dupage, and trains to the big city. If you're driving, we're a few minutes from the highway, as well. The space is outfitted with a memory foam queen bed, fold-out sofa, workspace, a TV with a variety of streaming services, free Wifi and a kitchenette for easy meals and snacks. We look forward to hosting you!

“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!

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!