Holiday rentals in Winfield

4.88 out of 5 average rating, 64 reviews

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 (w/ complimentary Hulu & Disney+!), 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!

4.96 out of 5 average rating, 23 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.

5 out of 5 average rating, 48 reviews

Guest house in Roselle

Roselle Studio

450 Sq Ft studio, located on the 2nd floor. Very cozy with private entrance and parking space. Queen size bed and a sofa sleeper, country setting, very quite, fire pit. This unit is above my work studio which I use when I get the time to tinker with a project. It is very safe place. Located less than 1 mile from the Metra train station. 20-25 minutes to O'Hare. Very close to shopping. Neighboring towns Schaumburg, Bloomingdale, Glendale Heights, Carol Stream, Bartlett, Elgin, Streamwood.

5 out of 5 average rating, 28 reviews

Guest suite in Wheaton

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.

4.86 out of 5 average rating, 58 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!

4.92 out of 5 average rating, 112 reviews

Home in Carol Stream

LakeHouse Stay! Hot Tub-Bar-Kayak-pool table-darts

Our beautiful home is the perfect place to gather with friends & family, relax, refresh, fish, have fun with your loved ones. It's the perfect home away from home with great views of the lake and on a quiet cul-de-sac. Stunning views of the lake while grilling or the firepit from the completely upgraded patio & the hot tub 🥂 🐶Up to 2 furry babies are allowed & they'll love the almost 1 acre fenced-in yard! (pet fee is extra & must be included at time of booking)

Guest house in Villa Park

4.92 out of 5 average rating, 133 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!

4.91 out of 5 average rating, 78 reviews

Flat in Warrenville

“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!

Guest suite in Naperville

4.95 out of 5 average rating, 465 reviews

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.

5 out of 5 average rating, 54 reviews

Guest suite in Wheaton

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.

Home in Winfield

4.83 out of 5 average rating, 6 reviews

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.