Holiday rentals in Winfield

4.92 out of 5 average rating, 192 reviews

Guest suite in Wheaton

✽ Charming Cottage ✽ close to College/Town/Station

Charming and cozy single family home fully renovated in a superb location! This house is walking distance to the Chicago metra rail system and Wheaton College, as well as a 6 minute drive to both downtown Wheaton and downtown Glen Ellyn! Relax and unwind in this darling home that we fell in love with! The health and safety of our guests is important to us. Due to COVID-19 we are taking extra care to professionally disinfect frequently and completely between every reservation UP TO CDC STANDARDS

4.89 out of 5 average rating, 55 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!

4.91 out of 5 average rating, 154 reviews

Home in Glen Ellyn

Home in Glen Ellyn

Beautiful 5 bedroom, 2.5 bath home in Glen Ellyn, fully furnished with everything you may need for a wonderful stay! Located in the peaceful suburbs of Glen Ellyn, the area is perfect for families or friends who would like a comfortable getaway. Located 40 minutes from downtown Chicago and Midway airport and 30 minutes from O'Hare airport. Located nearby major highways and shopping centers. Large, private and completely enclosed backyard perfect for kids to play in or a relaxed evening of BBQ!

4.96 out of 5 average rating, 213 reviews

Guest suite in Bartlett

Cozy & Spacious Suite in Quiet Neighborhood

This 950 sq. ft. guest suite is in a quiet, upscale neighborhood, less than 1/2 mile from Bartlett Hills Golf Club and a mile from Metra Train Station. 50 min. train ride to downtown Chicago. 10 min. walk to downtown Bartlett. A private entrance makes check-in easy and convenient, while offering privacy during your stay. Full kitchen, accessible bathroom, WIFI, and cable provided. Washer/Dryer available upon request. Pool is for registered guests only. Owners on site to assist if needed.

5 out of 5 average rating, 7 reviews

Hazelton's Wheaton Gem | Walk2 Starbucks & Target

Your family will be close to all amenities when you stay at this centrally-located home. It is completely renovated and is a beautiful retreat located just a few miles from Downtown Wheaton. It is also close to restaurants, public transportation, shopping and entertainment. This home is the perfect spot to stay if you are visiting Wheaton College or simply looking for a suburban escape. Beautiful backyard and deck is perfect for outdoor eating and grilling out. A true gem in Wheaton!

4.99 out of 5 average rating, 659 reviews

Guest suite in Geneva

A Suite within a Cozy cottage in Geneva Illinois.

Cozy private suite in the lower level. Guests have the suite to themselves. The bathroom is adjacent to the room and is private. There is a small fridge, a coffee maker, and a microwave oven. We are in Geneva, Illinois. We are LGBTQ+friendly. Our space is ideal for shorter stays and visitors on the go . Not suitable for staycations. Quiet area. Hosts live on the upper level and guests pass through our space to get to the suite. In a bind we can accommodate a 3rd guest and a pet. Welcome.

4.99 out of 5 average rating, 156 reviews

Flat in Aurora

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.

4.83 out of 5 average rating, 48 reviews

Little House on the Prairie-Path

Little House on the Prairie Path Cozy, gemütlich, hygge house in quiet unincorporated Wheaton, close to Lincoln Marsh, on the Prairie Path. International traveler decorated, newly refurbished in 2020. Very kid and pet friendly. Large back yard doubles as bird sanctuary and back porch overlooks pond with ducks, egrets, herons. Close to CDH (Central DuPage Hospital), Wheaton College, downtown Wheaton and Metra train to Chicago. Groceries, cafes, restaurants, amenities all around.

Guest suite in Saint Charles

4.98 out of 5 average rating, 173 reviews

The Cozy Den

Welcome to our cozy little corner of the world! We are located just a few blocks east of downtown St. Charles & the gorgeous Fox River and about an hour's drive/train ride to downtown Chicago. You’ll be staying in a renovated studio basement space (which doesn’t feel like a basement at all). It’s a completely separate space with its own entrance & electronic keypad. It is our priority to create an experience for you that is cozy, comfortable, and relaxing! Hope to see you soon!

Superhost

Home in West Chicago

4.9 out of 5 average rating, 139 reviews

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!”

Guest house in Villa Park

4.92 out of 5 average rating, 123 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!

4.92 out of 5 average rating, 51 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!

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Other great holiday rentals in Winfield

4.99 out of 5 average rating, 69 reviews

Home in Batavia

Bliss in Batavia near the Fox River

SarahRating, 5 stars1 week ago

What a lovely little quiet neighborhood to stay in! The home was perfect for our group of moms and kids horse showing at Lamplight. Anything we needed was responded to so quickly- and much appreciated!

Home in Streamwood

5 out of 5 average rating, 4 reviews

Modern & Cozy | Work & Relax

JoshRating, 5 stars1 week ago

Ann’s place was a very nice stay! The neighborhood was quiet, friendly, and safe! Which was very important for our family as we had children staying with us! Ann was also very friendly, responsive, and flexible with any accommodations. Ann’s place was very welcoming and clean. It felt right at home when we walked through the door! If you have a family or even a friend group, I highly recommend staying here!

5 out of 5 average rating, 17 reviews

Guest suite in Wheaton

The Garden Flat

MerreRating, 5 stars1 week ago

Gretchen's place is by far the best lodging I have ever had in my years of traveling world-wide! The Garden Flat is very clean, beautifully decorated & thoughtfully supplied with everything a guest might need. (She even had fresh muffins & a variety of snacks to greet me!) Gretchen is a creative artistic gal who has combined her considerable skills with a bit of whimsy to create a unique, comfortable space filled with high quality linens, fabrics, utensils, furniture, etc. To top off the delight, there is a beautiful inviting little garden in the back of the house that beckons guests to sit & relax. I hope to return one day, can highly recommend her place to other guests, and would absolutely give her ten stars if only I could!

Townhouse in Hoffman Estates

4.97 out of 5 average rating, 34 reviews

Game Room | Exercise Area | Firepit | Sanitized

Abdul AhadRating, 5 stars2 weeks ago

★★★★★ We had an absolutely phenomenal stay at Nayeli’s townhouse in Hoffman Estates, and I can’t recommend it highly enough! From the moment we booked, Nayeli’s communication was top-notch—warm, welcoming, and incredibly detailed. The pre-arrival message with clear instructions for check-in, parking, and amenities made everything seamless and stress-free. The townhouse itself is a gem—spotlessly clean, stylishly decorated, and equipped with everything you could possibly need. The newly remodeled bathroom in the bedroom hallway was a delightful surprise, with modern fixtures and a fresh, spa-like feel. The master bathroom was equally impressive, and the entire home felt cozy yet spacious. The beds were super comfortable, and the futons in the basement were a great bonus for our group, ensuring everyone had a cozy spot to sleep. One of the best experiences with Airbnb I had! Thank you for the unforgettable Stay!

Home in Wayne

4.59 out of 5 average rating, 534 reviews

Entire 5BR House - Wayne, IL (We are OPEN!).

MelissaRating, 5 stars5 days ago

This was the perfect place for my girlfriends and I to crash while in town for the night. The beds were incredibly comfortable. Would stay here again.

Superhost

4.64 out of 5 average rating, 22 reviews

4BR Family Home - Prime Location | LCP Collection

JonathanRating, 5 stars1 month ago

Great place, it says it’s for 8 guests, I had 6 and we all felt like we had our space but when we all wanted to stay in the living room and watch tv if you have more than 6 people it might be a little small to get together and watch a movie. But overall it was great no actual complaints.

Home in Winfield Township

5 out of 5 average rating, 6 reviews

Secluded Haven | Forest Views

JulianRating, 5 starstoday

What a gem! Beautiful, secluded house with a large backyard, a pond, a tree house, and a fire pit were a dream come true for our family's weekend getaway from our daily busy city lives. We'd all love to come back one day. We spent a lot of time in the backyard, but also visited the neighboring Kline Creek Farm as recommended by the hosts and went for a walk at the Red Oak Nature Center to dip our feet in the Fox River. Thank you!