Wheeling Holiday Rentals

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Holiday Rentals in Wheeling

Cozy Outdoor Space + BBQ | LCP Collection
9.0 out of 10, Wonderful, (2)
"Good"
The price is AU$817
includes taxes & fees
11 Nov - 12 Nov
Cozy Outdoor Space + BBQ | LCP Collection
Prime Location! 2BR Near Wrigley
9.2 out of 10, Wonderful, (5)
"Great location! Parking not included is a bummer."
The price is AU$320
includes taxes & fees
11 Nov - 12 Nov
Prime Location! 2BR Near Wrigley
Beautifully Set Up 2BR Space
10.0 out of 10, Exceptional, (14)
"Great apartment, plenty of room for 4 after a Cubs game, right by Wrigley. Would definitely stay here again for a ballgame."
The price is AU$319
includes taxes & fees
4 Nov - 5 Nov
Beautifully Set Up 2BR Space
At Home in Oak Park
3.5 star property
9.8 out of 10, Exceptional, (7)
"Great location in Oak Park- walkable, wondering area for restaurants and strolling through the beautiful neighborhoods."
The price is AU$408
includes taxes & fees
2 Nov - 3 Nov
At Home in Oak Park
Montrose Studio:Your Uptown Base
9.6 out of 10, Exceptional, (5)
"The property was exactly as pictured. The area was safe, had restaurants and coffee shops within a short walk. "
The price is AU$273
includes taxes & fees
3 Nov - 4 Nov
Montrose Studio:Your Uptown Base
1BR Apartment in Chicago
9.4 out of 10, Exceptional, (6)
"Good location for us. Host was easy to communicate with"
The price is AU$278
includes taxes & fees
4 Nov - 5 Nov
1BR Apartment in Chicago
Spacious 2BR Near Dining & Shops
8.0 out of 10, Very good, (6)
"Loved this sweet space tucked into a special neighborhood in the city. Space was clean & comfortable, wonderful shower & a nice respite from city life. "
The price is AU$327
includes taxes & fees
3 Nov - 4 Nov
Spacious 2BR Near Dining & Shops
Getaway Near ORD With Great Local Amenities
8.8 out of 10, Excellent, (3)
"Very nice and clean place to stay at. Great communication from property manager. I would absolutely stay here again!"
The price is AU$416
includes taxes & fees
11 Nov - 12 Nov
Getaway Near ORD With Great Local Amenities
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
8.8 out of 10, Excellent, (17)
"Good communication from owner regarding check in and options for nearby parking. I would stay here again."
The price is AU$353
includes taxes & fees
5 Nov - 6 Nov
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Relaxing Chicago Studio
10.0 out of 10, Exceptional, (23)
"Had a great stay. Great location. "
The price is AU$268
includes taxes & fees
4 Nov - 5 Nov
Relaxing Chicago Studio
A quiet stay while you are away
9.8 out of 10, Exceptional, (32)
"We stayed a few nights and everything was nice and clean. Thank you!"
The price is AU$300
includes taxes & fees
29 Oct - 30 Oct
A quiet stay while you are away
Historic Oak Park Residence
2.0 star property
9.6 out of 10, Exceptional, (12)
"Absolutely awesome "
The price is AU$415
includes taxes & fees
3 Nov - 4 Nov
Historic Oak Park Residence
Special Skevanston Space 2mi to Northwestern University & beach
9.0 out of 10, Wonderful, (21)
"Me, my friends, and girlfriend all stayed here together for the weekend. We attended collect-a-con over in Rosemont and then also did a little day trip to downtown Chicago for mine and my friends birthday! It was really nice staying here, super cozy and cute. Very nice neighborhood and neighbors were friendly :)"
The price is AU$349
includes taxes & fees
21 Oct - 22 Oct
Special Skevanston Space 2mi to Northwestern University & beach
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
10.0 out of 10, Exceptional, (45)
"Clean and quiet, perfect for nights to rest after exploring the city"
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Historic Oak Park Home
2.0 star property
10.0 out of 10, Exceptional, (5)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
The price is AU$415
includes taxes & fees
2 Nov - 3 Nov
Historic Oak Park Home
Chic Suite/Mins to L Train /Laundry/Free Parking
9.6 out of 10, Exceptional, (56)
"Good location. "
The price is AU$304
includes taxes & fees
21 Oct - 22 Oct
Chic Suite/Mins to L Train /Laundry/Free Parking
2BR Apt Beautifully Furnished
10.0 out of 10, Exceptional, (7)
"The property was as advertised and conveniently located near Wrigley Field! The property was clean. Instructions for check-in were clear and easy to follow. Parking could be an issue but after using the suggested SpotHero app, we were able to park less a block away. Thanks for hosting!"
The price is AU$330
includes taxes & fees
19 Oct - 20 Oct
2BR Apt Beautifully Furnished
Chic Urban Retreat Near Wrigley Field w/Parking
10.0 out of 10, Exceptional, (40)
"The property was amazing, clean and well organized. Parking was a breeze and check in was easy. Would recommend this place to anyone looking to stay in the area."
The price is AU$697
includes taxes & fees
20 Oct - 21 Oct
Chic Urban Retreat Near Wrigley Field w/Parking
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
10.0 out of 10, Exceptional, (40)
"We really enjoyed or stay at the apartment. Very quiet and nice location in a neighborhood."
The price is AU$342
includes taxes & fees
21 Oct - 22 Oct
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
Chic Studio - In Downtown Highland Park, by Metra
8.4 out of 10, Very good, (15)
"I enjoyed my stay at this property. It is in a great location, very unique and super clean! The host is really kind and helpful. "
The price is AU$223
includes taxes & fees
3 Nov - 4 Nov
Chic Studio - In Downtown Highland Park, by Metra
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Wheeling Hotel Reviews

Find out more about Wheeling

Everything you need to know about Wheeling holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Wheeling holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wheeling holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Wheeling holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wheeling. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wheeling holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wheeling holiday rentals we have selected for you start as low as AU$240 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Wheeling rentals

At Expedia, we put the best Wheeling holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Wheeling rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wheeling holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wheeling. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Wheeling?

Yes, there are holiday rentals close to the most popular sights in Wheeling, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Wheeling. Make sure you have time to check out the riverfront and ecotours during your trip.

What are some of the best holiday rentals that Wheeling has to offer?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: This holiday home rental outside of Wheeling offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

How many holiday rentals will I find in Wheeling?

Choose from 4 Expedia holiday rentals in Wheeling for a memorable holiday.

What can I see and do in Wheeling?

Explore the area and family-friendly sights such as Six Flags Great America, or get out into nature at a spot like Heritage Park. In the wider area, you’ll find Naval Base Great Lakes and Chevy Chase Country Club.

What are holiday rentals like in Wheeling?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Wheeling. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for family gatherings.