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

Home in Northbrook

4.98 out of 5 average rating, 83 reviews

*King bed *Outdoor Living *Sought-After Area

Welcome to our sophisticated ranch style home, nestled in the serene, central Chicago neighborhood of Northbrook. This carefully curated home offers a peaceful retreat in a walkable neighborhood with nearby shopping and dining. With its elegant decor, comfortable furnishings, and modern amenities, the home provides a haven of relaxation. Whether you're enjoying a cup of coffee on the private patio or exploring the area, this home provides the perfect backdrop for a memorable vacation experience.

Top guest favourite

Home in Des Plaines

4.95 out of 5 average rating, 42 reviews

Spacious Home Studio 10 Min From O’Hare & Rosemont

Clean and well appointed lower level of owner-occupied home with private in/out access separated from the main level. The suite-style space includes a generous living area with two large couches, 49” smart TV w/ sound system, king bed, full bathroom, kitchenette w/ table, washer/dryer & work desk. Great location 5-10 minutes from O'Hare, Allstate Arena, Rosemont and Rivers Casino with ample transportation options. Property is within short walking distance of grocery stores, gym, parks & more.

Top guest favourite

Home in Prospect Heights

4.94 out of 5 average rating, 34 reviews

The Executive Residence 5400sqft/5 Bed/4.5Ba 0.8ac

Experience privacy, comfort, and luxury in a safe, quiet residential area. Book your stay today for an unforgettable experience! Guest Favorite & Rare Find +super clean +extra spacious A luxurious 5400 sq ft home in Prospect Heights, set on a private 0.8-acre lot surrounded by tall pine trees. Features 5 bedrooms, 4.5 bathrooms, a huge backyard, and off-street parking for 3 cars. - 2 min walk to the lake - 5 mi from Kohls Children's Museum - 8min from Mount Prospect metra -14 mi from ORD

Top guest favourite

Home in Arlington Heights

4.99 out of 5 average rating, 72 reviews

Home in the Heights

Take it easy at this unique and tranquil Universally Designed Ranch home close to downtown Arlington Heights, train and major highways. This is a perfect little getaway when you’re visiting the Chicagoland. This home is ideal place for working individuals, travelling professionals on assignment to nearby hospitals/skilled nursing facilities and other businesses. The house features an updated kitchen, remodeled bathrooms, spacious yard, outdoor furniture/portable fireplace, and two-car garage.

Guest favourite

Flat in Highland Park

4.83 out of 5 average rating, 131 reviews

Chic Studio in Downtown Highland Park - By Metra

Discover our elegant studio unit in Highland Park, now featuring FREE parking! This simple yet comfortable space is perfect for couples, concert-goers, and small families. You'll find all the essential amenities you need, including a fully stocked kitchen, laundry facilities, and reliable Wi-Fi. Our location is ideal for exploring downtown Highland Park, with convenient access to top attractions, restaurants, and shops. Book now and discover your perfect home away from home on the North Shore.

Guest favourite

Guest suite in Arlington Heights

4.93 out of 5 average rating, 54 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

Guest suite in Riverwoods

4.96 out of 5 average rating, 424 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.

Guest favourite

Flat in Libertyville

4.82 out of 5 average rating, 87 reviews

131 E. Park Ave - Unit 306

Keep it simple at this peaceful apartment walking distance to fantastic downtown Libertyville. Very nicely maintained building with elevator. 7 miles to Great Lakes Naval Base. Super clean unit with all brand new furnishings. HD smart TV's with cable in both the living room and bedroom. There is a comfortable rollaway bed behind the couch that is perfect for one person. Fast Wi-Fi with dedicated work desk. Ample free parking right in front of the building. On-site laundry one floor down.

Guest favourite

Home in Arlington Heights

4.95 out of 5 average rating, 95 reviews

White House, 5 Beds

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!

Guest favourite

Home in Palatine

4.82 out of 5 average rating, 57 reviews

Private Room w/ attached bath and personal kitchen

The entire basement is for the guest except few restricted areas in the basement. This a quiet bedroom located in the look out 1500 sq foot basement which has a queen bed, attached bath ( with jacuzzi tub), private kitchen ( with refrigerator, dishwasher, stove) entirely for guest use, sitting area and a theatre room ( with owners permission) and high speed WI-FI. The location is great and very close to USMLE. DISCOUNT PROVIDED FOR WEEKLY AND MONTHLY RENTAL, PLS ASK

Guest favourite

Home in Palatine

4.96 out of 5 average rating, 82 reviews

Cheerful 3- Bedroom!

Our guests will be welcomed to a freshly renovated home that is walking distance to shops, Restaurants, groceries and the Metra train station that will get you downtown to Chicago! All beds/bedding are brand new! All new hardwood floors, new kitchen, brand new appliances, new towels, etc. Come stay in our fully appointed guest house! Grill, fire pit, outdoor seating included. Mid-century home with all the modern necessities. We kept the pink vintage bathroom!

Top guest favourite

Flat in Palatine

4.97 out of 5 average rating, 178 reviews

Huge Sofa-King Bed-Easy Parking-Private Deck-Retro

MId Century Modern 1 Bedroom With Private Entrance in Downtown Palatine! More Than 170 5 Star Reviews ★★★★★ "This place is amazing. It is so cute and cozy. The location is amazing, walking distance to everything downtown Palatine has to offer.." Abbey - February 2025 700sf Retro Apartment with a King Bed & Private Outdoor Space. Safe Off Street Parking. Just Steps to Public Transportation, Bars, Restaurants & More.