Holiday 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.

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

The Secret Garden

Summer is COOLER in Geneva! Located just 3 blocks from shops and restaurants in beautiful, downtown Geneva. Our space can sleep up to 4 comfortably. We offer amazing amenities like plush bed & linens, array of coffee and teas and goodies, 50" flat screen smart tv for watching movies after a day of fun in Geneva. Beautiful bath equipped with everything, including homemade salt scrub. A secure, separate entrance to come & go. It is a basement soace so ceilings are lower than average home.

2BR Family Escape! Pool, Pickleball, Play Room

A premium, resort-like experience in a professionally managed 2 bedroom / 2 bathroom property, providing the perfect balance of luxury and comfort for business travelers and families. Enjoy the pool, pickleball court, kids play room, courtyard w/ firepits, fitness center, pool table, and sauna - convenience is at your fingertips! Explore nearby downtown Naperville (8 mins), classy Oakbrook Terrace, the beautiful Morton Arboretum and downtown Chicago, a short drive or train ride away!

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.

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!

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 (9 beds), 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 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!

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.

Charming & Cozy Wheaton Stay- Great Location!

You are booking a Cozy, Modern, and SPACIOUS Basement Apartment with a Private Entrance, Exclusive Laundry Room, and a large open-concept Guest Suite! Located in one of Wheaton’s most charming neighborhoods – it’s less than a mile from Wheaton College and the Metra train station, and 1.5 miles from Wheaton’s delightful downtown. Host occupies the separate first floor.

Sunroom Oasis minutes from Metra

Enjoy the serenity of a 4-season sunroom overlooking a stunning backyard while being walking distance to the Metra into the City! A short drive away from some of the best Illinois downtown suburbs and parks. Stay in a beautifully furnished 3-bed 2-bath home, with a dedicated office that comes with high-speed internet.

Heaven: 4 BR/4.5 BTH - Spacious w/ Sauna & Bar

Welcome to Heaven – Your Gorgeous Retreat Step into pure comfort and luxury in this spacious, modern home designed for families, friends, and travelers looking for the ultimate getaway. From soaring ceilings to designer finishes, every detail is meant to wow you. Heaven really is a place on Earth.