Holiday rentals in Wheeling

Cozy 2-Bedroom Cottage Near Downtown Highland Park

Step into a warm, inviting retreat where comfort meets character! This beautifully updated suite features two cozy bedrooms, a private bathroom, and thoughtfully decorated living spaces in a modern farmhouse style. Nestled in the heart of Highland Park, you’re steps from great restaurants, boutique shops, scenic trails, and parks, plus a golf course across the street and just 1.5 miles from Lake Michigan. Whether it’s a family getaway or a business trip, it’s your perfect home away from home!

Single Family home/ Schaumburg

"Your home away from home" is awaiting for your short or extended stay. Entirely updates, and fully equipped for your convenience, this 3 beds, 2 full baths house, with specious backyard, BBQ and patio is going to make your most comfortable experience of exploring Schaumburg and the surrounding areas. Conveniently located just 15 min from O'Hare airport, 5 min from Woodfield mall, 8 min from soon-to be home of the Chicago Bears, all major interstates, shopping, one of a kind dining and much more

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!

5 star stay at 6 bed,3 bath Chicago O'Hare Airport

This unique place has a style of its own. It's spacious with 5 bedrooms, 3 full bathrooms, single family home that is inviting for you to relax and enjoy while being close to restaurants and shopping. We are located 10 minutes from Chicago Executive Airport and 15 minutes from O'Hare International Airport. 10-15 minutes from Allstate Arena, Rosemont Convention Center, Fashion Outlets of Chicago and Rivers Casino. Downtown Chicago is 30 minutes away with easy access to I-94 & I-294 expressways

Master qtr close to nature & easy urban facilities

This amazing prairie style home sits on 2 acre land surrounded by lush lawn and majestic oak trees - a nature lover's dream with unparalleled serenity. Vacation-like setting blends country-like quiet with nearby conveniences including shopping, trains, restaurants, highways, Ravinia (18 MINs drive). 5 MINs to I 294. 20 MINS to O'HARE; 5 Mins to Discover, Baxter; 10 MINs to Walgreens Deerfield campus, TRINITY INT'L UNIVERSITY; 15 MINS to Lake Forest Academy. 25 MINs to Great Lakes Navy Base.

Charming space w/ use of deck and yard

Charming home in Highland Park. The space is my in-law suite which is in the lower level of my home and has its own full size kitchen and bathroom. I live up-stairs with my 3 small dogs so I will be available if you need anything during your stay. The in-law suite is set up like a studio and has ONE queen bed, a separate closet area and laundry. Please note- the suite is in the basement (stairs), but there is natural light. You have use of the deck/yard if desired. No stays over 3 weeks.

Private Jefferson Park Home

Welcome to Chicago's very own Jefferson Park! Just-renovated two bedrooms, one bathroom unit with private access -2 Blocks to Metra - 10 min to O'Hare, Rosemont & Allstate Arena - 20 min to Downtown/Wrigley Field - Free High-Speed Wifi & Smart TV - Ample/Free Street Parking - Access to Interstate 90 - Walking Distance to Restaurants & Coffee - Brand New Stove, Refrigerator, and All-in-One Washer/Dryer - Bedrooms with Brand New Ceiling Fans - Convenient Keyless Entry on YOUR Schedule!

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.

Welcome Home! 4BR 2.5BTH House | Arlington Heights

We are excited to welcome you to this charming and spacious apartment if you're visiting Arlington Heights. We are very close to ORD airport, Great Lakes Naval Base and Chicago. Working, relaxing, living. Our space has all the other essentials you need for your stay. - Contact-free check-in - 24/7 virtual support - Xfinity Wi-Fi - Fresh towels and bathroom essentials - Pre-cleaning before your arrival - Fully equipped kitchen - NETFLIX and HDMI for streaming

Cozy Corner Plains

Modern Des Plaines Stay Near O'Hare Cozy town house in Des Plaines Comfortable Stay Minutes from Chicago Stylish Unit Near O'Hare Airport Quiet & Cozy Des Plaines Getaway Modern Retreat Close to Downtown Chicago Bright & Clean Stay Near Restaurants & Shops Charming Apartment with Easy Airport Access Relaxing Home Base Near O'Hare & Rosemont Convenient Des Plaines Stay with Free Parking

Elegance: 4BR - 2 BT Spacious Ranch w/ Basement

Welcome to this beautiful and spacious 4-bedroom, 2-bath ranch home featuring a finished basement and beautiful bathrooms. Designed with comfort and space in mind, this home offers plenty of room to relax, gather, and unwind—perfect for families, groups, or extended stays. A bright, inviting layout and thoughtful updates make this a place you’ll truly enjoy coming home to.

The Quiet Cove - Newly Renovated

This beautifully updated 3-bedroom, 1.5-bath ranch offers modern comfort and privacy—perfect for families, couples, or groups. Enjoy a relaxing suburban stay with all the comforts of home. Conveniently located minutes from I-294, just 9 miles from O’Hare Airport and 20 miles from Great Lakes Naval Base. Ideal for both quick getaways and extended stays.