Wheeling holiday lettings

We found 318 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Wheeling to find one that's perfect for your trip. Whether you're going on holiday with family or friends, holiday homes have the amenities that you need and want for your stay, which might include a garden and pool. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Wheeling

Showing deals for:16 Jan - 23 Jan

Image gallery for Schaumburg Pool House

Patio is summer ready for chilling by the pool!
9.6 out of 10, Exceptional, (18 reviews)
Exceptional
(18 reviews)

Schaumburg Pool House

Schaumburg, IL

9% off
Price is £2,707
for 7 nights, 1 home
£387 per night
includes taxes & fees
Schaumburg Pool House

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Delight in the riverfront landscape of Wheeling

The riverfront and lake provide a pleasant backdrop to your holiday home in Wheeling. This city's restaurants, shopping and ecotours draw many visitors. Naval Base Great Lakes and Six Flags Great America are just a couple of the must-see attractions in the area. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Sightseeing in and around Wheeling

Do you want to discover top things to see and do during your stay? Venture out of your cosy holiday rental and check out everything that Wheeling has to offer. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Six Flags Great America (15.8 mi / 25.4 km)
  • Chevy Chase Country Club (1.4 mi / 2.3 km)
  • Northbrook Sports Complex (4.3 mi / 6.9 km)
  • The Glen Club (6.2 mi / 10 km)
  • Conway Farms Golf Club (6.7 mi / 10.7 km)
  • LEGOLAND® Discovery Center (8.7 mi / 14 km)

Exploring the natural landscape of Wheeling

Whether you're an adventurous traveller or just want to appreciate the scenery, Wheeling is a great place to get outside. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Heritage Park (0.4 mi / 0.7 km)
  • Chicago Botanic Garden (7.3 mi / 11.7 km)
  • Lake Park (8.9 mi / 14.3 km)
  • Fox River Preserve (15 mi / 24.1 km)
  • Portage Park (15.3 mi / 24.6 km)
  • Loyola Beach (16.7 mi / 26.8 km)

Travelling to and around Wheeling

The nearest airport is in Chicago, IL (PWK-Chicago Executive), located 2.2 mi (3.5 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Chicago O'Hare International Airport (ORD), which is 11.3 mi (18.1 km) away.

If you prefer train travel, the main station is Wheeling Station.

Frequently asked questions

What is the best area to stay in Wheeling when booking a holiday rental?
When considering a holiday rental in Wheeling, Illinois, the best area to stay in is the downtown district. This vibrant neighbourhood offers a great mix of convenience and charm, making it an ideal base for your visit. You'll find a variety of properties available, ranging from cosy apartments to spacious townhouses, ensuring there's something to suit every traveller's needs.

Staying in downtown Wheeling places you within easy reach of top attractions such as the famous Wheeling Town Centre, which boasts a selection of shops and dining options. The nearby Riverwalk is superb for leisurely strolls along the scenic Des Plaines River, providing a lovely backdrop for outdoor activities. Additionally, the area is known for its rich cultural offerings, including the historic Wheeling Park District, which features parks and recreational facilities that are great for family outings.
How much does it cost to rent a holiday home in Wheeling?
Prices for holiday rentals in Wheeling vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Wheeling to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Wheeling holiday house rentals?
You can find great discounts on house rentals in Wheeling on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Wheeling?
In Wheeling, holiday houses are the most popular type of rental accommodation, with several available throughout the area. These properties typically offer spacious layouts, featuring multiple bedrooms, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups. Many holiday houses also include outdoor spaces such as private gardens or patios, providing a superb setting for relaxation after a day of exploring the local attractions.
Are there any family house rentals in Wheeling?
In Wheeling, Illinois, there are several family-friendly house rentals available, making it an ideal destination for those travelling with children. Many of these homes are located close to local parks, providing ample space for outdoor activities. Visitors can expect amenities such as spacious living areas, fully equipped kitchens for preparing family meals, and comfortable bedrooms to ensure a restful night's sleep.
Can I find long-stay holiday rentals in Wheeling?
A long-stay holiday rental in Wheeling is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Wheeling?
In Wheeling, there are several pet-friendly house rentals available, offering a variety of amenities to ensure a comfortable stay for both you and your furry companions. Many of these properties feature spacious backyards, making them great for pet playtime, as well as modern kitchens and open living spaces ideal for families.
Are there any remote work holiday rentals in Wheeling?
In Wheeling, Illinois, there are several holiday rentals that cater to remote workers. These accommodations typically come equipped with essential amenities like desks and comfortable chairs, along with high-speed Wi-Fi to ensure a productive work environment. Many properties also offer spacious living areas, allowing for both work and relaxation. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Wheeling holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Wheeling with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Wheeling?
In Wheeling, holiday rentals typically feature a range of popular amenities to enhance the stay. Most accommodations include a well-equipped kitchen, allowing guests to prepare their own meals, and many also have a coffee maker for that essential morning brew. Additional conveniences often found are cookware, dishware, and utensils, making it easy for travellers to dine in. Many rooms also come with a dishwasher and a microwave, ensuring that guests can easily manage their cooking and clean-up.
When is the best time to visit Wheeling for a holiday rental?
The best time to visit Wheeling is during the peak travel season from June to August, with July being the most popular month. This vibrant period attracts families and adventure seekers eager to relish the warm weather, explore local parks, and enjoy a variety of outdoor events. Visitors can take advantage of the pleasant temperatures, typically in the mid to high 20s Celsius, making it ideal for activities such as hiking, picnicking, and enjoying the numerous festivals that take place.

Wheeling's summer atmosphere is buzzing with energy, and you'll find plenty of fellow travellers enjoying everything from live music to food festivals. The proximity to attractions like the Chicago Botanic Garden and the scenic Des Plaines River adds to the allure, offering ample opportunities for sightseeing and relaxation.

If you're looking for a more budget-friendly option, consider visiting in October. This month provides a lovely backdrop with the beautiful autumn foliage and fewer crowds, making it great for leisurely walks and exploring the local shops without the hustle and bustle of peak season.
How early should I book a Wheeling holiday rental?
Book your Wheeling holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Wheeling home rental booking on Vrbo?
To find Wheeling holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Wheeling holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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