Wheeling Holiday Rentals

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Our top choices for Wheeling holiday rentals

9.8 out of 10, Exceptional, (69 reviews)
"Really amazing place. Adorable house, plenty of space, conveniently located. Great linens on the beds & amenities in the bathroom. Owner was incredibly flexible and responsive and great to work here. Had three visitors from Europe and they absolutely loved the place and had a great time. Would 100% stay here again the next time we're in the area. "
United States
Erika H.
The price is NZ$549
includes taxes & fees
22 Mar - 23 Mar
Quaint Bungalow, near Great Lakes Naval Base

Apartment in Lincoln Square

Nice 1BR Spot, Unwind & Relax
9.8 out of 10, Exceptional, (28 reviews)
"Very clean & cozy! Conveniently located by great shopping & restaurants!"
United States
SHERI C.
The price is NZ$299
includes taxes & fees
22 Mar - 23 Mar
Nice 1BR Spot, Unwind & Relax

Holiday Home in Gages Lake

Navy Family home -Near Lake 4BR Hot Tub
10.0 out of 10, Exceptional, (4 reviews)
"Nice location for our family attending our daughter's graduation from Navy Basic at Great Lakes. "
United States
Judson S.
The price is NZ$1,258
includes taxes & fees
29 Mar - 30 Mar
Navy Family home -Near Lake 4BR Hot Tub
9.6 out of 10, Exceptional, (64 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is NZ$553
includes taxes & fees
22 Mar - 23 Mar
2-bedroom apartment just 2 minutes drive to Wrigley Field

Apartment in Near West Side

Your Perfect 2BR Home
8.4 out of 10, Very good, (15 reviews)
"Great location! "
United States
Kourtney K.
The price is NZ$393
includes taxes & fees
23 Mar - 24 Mar
Your Perfect 2BR Home
10.0 out of 10, Exceptional, (7 reviews)
"Had a great experience here, and also close to the airport!"
United States
Yafeat D.
The price is NZ$210
includes taxes & fees
22 Mar - 23 Mar
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

Apartment in Uptown

Uptown Studio Gem Sum
7.4 out of 10, Good, (6 reviews)
"The neighborhood was perfect for me. I’d like to book the same property again because of the location.The only problem was checking in. The address was wrong and if I wasn’t raised in that part of Chicago I would have been very confused.Plus I checked in late at night. It wasn’t an easy process. Next time it will be diffeeent."
United States
Darryl C.
The price is NZ$332
includes taxes & fees
22 Mar - 23 Mar
Uptown Studio Gem Sum

Holiday Home in Oak Park

A quiet stay while you are away
9.8 out of 10, Exceptional, (35 reviews)
"Everything was very comfortable and Jay did a great job of showing the house. I would definitely come back again"
United States
Fred D.
The price is NZ$428
includes taxes & fees
20 Apr - 21 Apr
A quiet stay while you are away
10.0 out of 10, Exceptional, (17 reviews)
"Host and amenities were great!"
United States
Jeff P.
The price is NZ$375
includes taxes & fees
23 Mar - 24 Mar
Little Fox Cottage - A Cozy Riverview Getaway
9.0 out of 10, Wonderful, (4 reviews)
"Amazing stay, great host! "
United States
Aaron L.
The price is NZ$581
includes taxes & fees
16 Apr - 17 Apr
Tiny Home Retreat with hot tub

Apartment in North Center

1BR Apartment in Chicago
9.0 out of 10, Wonderful, (17 reviews)
"Very clean and the host was easy to work with. "
United States
Scott S.
The price is NZ$331
includes taxes & fees
6 Apr - 7 Apr
1BR Apartment in Chicago
10.0 out of 10, Exceptional, (59 reviews)
"This is a cozy little home close to all the things we love about visiting Wheaton. "
United States
Nancy F.
The price is NZ$520
includes taxes & fees
23 Mar - 24 Mar
✽ Charming Cottage ✽ close to College/Town/Station
9.6 out of 10, Exceptional, (20 reviews)
"Very nice place and neighborhood."
United States
Charles R.
The price is NZ$609
includes taxes & fees
22 Mar - 23 Mar
Spacious, lovely 2bed 1bath with free parking
10.0 out of 10, Exceptional, (8 reviews)
"Everything was as described. I would stay here again."
United States
Brent S.
The price is NZ$420
includes taxes & fees
22 Mar - 23 Mar
Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola
8.2 out of 10, Very good, (22 reviews)
"Easy to access, big place, great for a group that needs to have several rooms and beds. Would definitely stay again"
United States
JOSE S.
The price is NZ$515
includes taxes & fees
23 Mar - 24 Mar
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
9.6 out of 10, Exceptional, (98 reviews)
"Cozy place, host was very helpful and responded quickly to all my concerns. I would definitely stay there again. "
United States
Deborah R.
The price is NZ$441
includes taxes & fees
24 Mar - 25 Mar
Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Apartment in Oak Park

The Oak Park Loft
2.0 star property
10.0 out of 10, Exceptional, (5 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is NZ$442
includes taxes & fees
30 Mar - 31 Mar
The Oak Park Loft

Apartment in Oak Park

Oak Park Queen
8.2 out of 10, Very good, (33 reviews)
"The property was very clean and comfortable. Good location. The owner was responsive."
United States
Susan S.
The price is NZ$382
includes taxes & fees
22 Mar - 23 Mar
Oak Park Queen
9.8 out of 10, Exceptional, (73 reviews)
"Apartment is as advertised. Nicely stocked, large, clean, comfortable, nice natural light, quiet, great location, full size appliances, easy access. "
United States
Susan G.
The price is NZ$505
includes taxes & fees
25 Mar - 26 Mar
Cozy, Comfortable and Convenient apartment. Close to everything!

Apartment in Rogers Park

Great Layout – Spacious 2BR Apt
10.0 out of 10, Exceptional, (5 reviews)
"Clean, comfortable, and would definitely stay again!"
United States
KM W.
The price is NZ$371
includes taxes & fees
23 Mar - 24 Mar
Great Layout – Spacious 2BR Apt
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 favorite 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 depends 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 NZ$210 per night. Entering your travel dates in the search wizard you might find 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?

ENVITAE Hotel / 4BR Luxury Modern Apartments: This holiday home rental outside Wheeling is located in the city centre, and offers a BBQ, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in Wheeling?

Choose from 3 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.