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Holiday rentals in Wheeling

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Top-rated holiday rentals in Wheeling

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A modern kitchen and living area are showcased within an open-concept space. The kitchen features stainless steel appliances and a large island with seating for three. The cozy living area includes comfortable seating and a low wooden coffee table, complemented by warm wooden flooring.
Flat in Chicago
5 out of 5 average rating, 80 reviews

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

Guest favourite
Home in Des Plaines
5 out of 5 average rating, 16 reviews

Cozy Home near airport O’Hare

Welcome to your cozy home away from home! This peaceful suburban house is perfect for families, couples, or business travelers looking for a quiet stay near Chicago. Located just 15 minutes from O’Hare Airport, our home offers: A private backyard – great for relaxing A quiet neighborhood with a nearby playground Fully equipped kitchen & comfortable living space Fast Wi-Fi, smart TV, free parking ✅ Family-friendly ✅ Self check-in ✅ Clean, quiet, and safe Book your stay and make yourself at home!

Guest favourite
A modern living area features a grey sectional sofa and a light-colored armchair positioned around a soft area rug. Two windows allow natural light to enter, and wall art decorates the walls. Steps lead to an upper level, contributing to an open and inviting layout.
Flat in Avondale
4.94 out of 5 average rating, 109 reviews

Best Deal in Chicago | Great Food & Free Parking

Clean & modern Avondale apt close to Blue Line, perfect for urban explorers! Stylish decor, comfy bed, and a cozy ambiance await. Explore nearby cafes, bars, and boutiques, or hop on the train for downtown adventures. Easy to access & great neighborhood. Easy permit parking (free passes provided) on street allows for the ability to drive or take public transportation wherever you want to explore. Avondale has been voted one of the best neighborhoods in Chicago! Come see what the fuss is about.

Top guest favourite
A bright living space features a spacious sectional sofa accented with blue and white cushions. A round coffee table sits atop a decorative rug. A large clock adorns the wall, while a dining area with a wooden table and chairs is visible in the background.
Guest suite in Arlington Heights
4.94 out of 5 average rating, 63 reviews

Cozy Chicago Suburban Apartment

Welcome to our cozy apartment, perfect for solo travelers or couples looking for a comfortable stay in the quiet Northwestern suburbs of Chicago. Located in a quiet and serene neighborhood, this apartment offers easy access to all the best restaurants, cafes, and shops. Just 23 mins away from O’hare International Airport, 15 mins to Schaumburg Convention center & Woodfield Mall, and about 40 mins from the Chicago Downtown. Lake Arlington is a 10 mins walk away for Kayak and park activities.

Guest favourite
A well-defined stone pathway leads to the entrance of the prairie-style home, bordered by lush green grass and neatly trimmed hedges. Hanging flower baskets add vibrant touches above the cozy seating area, surrounded by the serene backdrop of towering oak trees.
Guest suite in Riverwoods
4.95 out of 5 average rating, 449 reviews

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.

Top guest favourite
A spacious living room is featured with a comfortable sectional sofa, accented by several pillows. A coffee table is centered on a soft area rug, while large windows allow natural light to illuminate the space. Potted plants add a touch of greenery to the decor.
Flat in Highland Park
5 out of 5 average rating, 59 reviews

Full Apartment green oasis in law suite

Beautiful & spacious 1 bedroom, 1 bath in law apartment. New windows with green views. Fragrance free home. There are Curtains in the living room & kitchen. Designated Parking onsite. Full kitchen full sized stainless appliances, private stackable washer and dryer machines & beautiful tile throughout. Bring slippers tile can be chilly to touch - if barefoot. Starbucks, parks, restaurants, dry cleaners & Jewel walking distance from apartment. Whole Foods & Target 7 min. drive. NO PARTIES.

Guest favourite
A comfortable living area is designed with a gray sofa and a black coffee table, complemented by a dining table. A work desk is positioned near large windows, allowing natural light. A ceiling fan is visible, and a flat-screen TV is mounted on the wall.
Flat in Libertyville
4.88 out of 5 average rating, 34 reviews

305

Kick back and relax in this calm, stylish space. This peaceful, quiet apartment is walking distance to beautiful downtown Libertyville. The building is very nicely maintained with an elevator. Located 7 miles from Great Lakes Naval Base and 35 miles from downtown Chicago. The unit is very clean with all brand new furnishings and appliances including HD tv's in both the living room and bedroom. Free ample parking. On-site laundry one floor down. Fast wifi with a dedicated work space.

Guest favourite
Home in Glenview
4.92 out of 5 average rating, 13 reviews

Charming private guest suite in quiet neighborhood

Relax with the family in this private guest suite with a private entrance in a safe and peaceful neighborhood in Glenview. With your own private entrance, you can enjoy this 1 bedroom / 1 bathroom guest suite where you will be sleeping on egyptian cotton sheets and memory foam pillows for extra comfort. The suite is equipped with a microwave, mini fridge, Nespresso, and water kettle. There is no stove. A portable baby crib is available upon request. There are two free parking spaces.

Guest favourite
A spacious living area features a large sectional sofa, arranged around a central coffee table. Natural light fills the room through expansive windows adorned with sheer curtains. Light wood flooring complements the neutral color palette, creating a comfortable and airy environment.
Home in Arlington Heights
4.93 out of 5 average rating, 107 reviews

Stylish 4 bedroom home in Arlington Heights

Completely updated and fully furnished single family ranch home with lots of space less than 10 minutes away from downtown Arlington Heights. The home is equipped with 3 Queen beds, 1 full bed, a sofa bed, a 65 inch tv in the living room with a sound bar and subwoofer, 43" tv's in 3 of the bedrooms, and a 32' tv in the fourth bedroom. The large deck in the back is great for entertaining. The home has a pool table which is great for entertaining as well. Book your stay with us today!

Top guest favourite
A serene living area features a large sliding glass door leading to a deck with unobstructed views of Round Lake. Natural wood accents adorn the wall, while a plush sofa and a small coffee table create a relaxing seating space.
Home in Round Lake Beach
4.99 out of 5 average rating, 181 reviews

Round Lake Getaway Retreat

Looking for a calming, peaceful lakeside getaway for you and your loved one? Come stay at our remodeled retreat with private waterfront access to Round Lake. Enjoy peace and reflection meditating on the spirited lake waters rolling into shore. Wake up to inspirational lake views with soul warming coffee, tea or cocoa. Savor deep or lazy conversation with your loved one, surrounded by dreamy décor and captivating nature. Come and relax, restore, and rejuvenate by the lake!

Guest favourite
A well-appointed bedroom features a spacious bed with soft linens, flanked by two bedside tables with lamps. Natural light filters through the window, with sheer curtains offering privacy. A potted plant adds a touch of greenery, while a decorative rug enhances the inviting ambiance.
Home in Des Plaines
4.94 out of 5 average rating, 32 reviews

Designer Furnished + Game Room | LCP Collection

Discover comfort and convenience in this newly remodeled 3BR, 1.5-bath retreat in Des Plaines. Just a 2-min walk to Shagbark Lake, and minutes from O’Hare, the Convention Center, and Allstate Arena, it’s the perfect base for exploring Chicago. Relax in the spacious living room, enjoy meals in the fully equipped kitchen, and unwind in style. Full access to the home and outdoor spaces makes this ideal for families and groups alike.

Guest favourite
A warm-toned room features wooden wall paneling and large windows adorned with draped curtains. A small round table sits at the center, complemented by a floral arrangement. Natural light enters through the windows, creating a bright ambiance in this cozy space.
Guest house in Des Plaines
4.91 out of 5 average rating, 35 reviews

Where Style and Substance Coexist. New Rehab

9min - Ohare ORD airport 5min - Casino 4min - Allstate arena 3min - Hway 1st floor - 14 steps Charming 2-bedroom ( 1 bed queen, 1 couch for one person - living room, 1 foldable single bed ) guest house above the garage. One of the bedrooms is set up as an office with single foldable bed, perfect for working from home. Enjoy modern living with a new bath and ample space. Ideal for those seeking comfort and convenience.

Popular amenities for Wheeling holiday rentals

Frequently Asked Questions

  • Do house rentals in Wheeling have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Wheeling. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Wheeling have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Wheeling. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Wheeling?

    Wheeling has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there pet-friendly vacation rentals in Wheeling?

    Four-legged friends are welcome in Wheeling. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Do house rentals in Wheeling have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Wheeling. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Wheeling?

    Experience the best of Wheeling with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • What are the most popular amenities for House Rentals in Wheeling?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there vacation rentals with a dedicated workspace in Wheeling?

    Yes! Work meets play with ease at over 10 vacation rentals in Wheeling featuring dedicated workspaces. Stay connected and productive in your home away from home.

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