Wheeling Vacation Rentals from CA $165: Short-Term Rentals for 2025

Q: What are some of the best vacation rentals that Wheeling has to offer?

Luxury Home Away From Your Home : This vacation home rental outside of Wheeling is equipped with a barbecue grill, air-conditioning, and free WiFi to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

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Vacation Rentals in Wheeling

"A clean, spacious, affordable option in a perfect location in Lincoln Park. Plan to return in the future."

"Had a great time at Ms. Linnie’s place! She was incredibly responsive and helpful. The house was clean and comfortable, and I loved that there were 2 full bathrooms! I was a little nervous about the neighborhood as we were definitely looked at as outsiders, but no one bothered us and we walked to Maxwell Street Polish and back just fine (which is fantastic, btw). I did love the gated yard in back with two parking spots, so we had our own space. Would definitely stay again!"

"convienent location "

"We were very pleased with the property. Stayed there over the Thanksgiving holiday & weekend while visiting my older daughter. Nice neighborhood & easy location to get to other parts of the city. Everything was as depicted in the description and communication with management was excellent. Would stay here again."

"Fantastic location and an outstanding host! I had an amazing stay. The space was ideal for my needs, offering a comfortable and convenient setting to assist my daughter with her wedding preparations. It had everything I was looking for—well-equipped with great amenities and in a prime location. The property was spotless, peaceful, and provided everything needed for a smooth and enjoyable experience. Easy street parking was always available! I highly recommend this place to anyone looking for a...

"Great host, great location and great stay. Harry is a great host and was easy to work with on the stay. Thank you!"

"This property is in a great location that is quiet and convenient. The property was extremely clean and had essentials for our stay. This property was a great option for our family to stay together and there was plenty of room for all 6 of us adults. Fantastic place. Most definitely would stay again!!!"

"Everything was as advertised. Neighbors with dogs barking in the night and car honking/other outside elements can be disruptive if you're a light sleeper. Very quick and fast communication with host even at 2am. Would recommend."

"excellent, all on time and very communicative at the time that the place was very pleasant "

"Very clean, extremely nice home. "

CA $408 total

includes taxes & fees

Jan 23 - Jan 24

"The house was very clean and spacious. A lot of activities to do "

CA $1,550 total

includes taxes & fees

Jan 27 - Jan 28

"This was a great place to celebrate the holidays. Kitchen was well stocked with cookware and utensils to make Christmas dinner and we had plenty of room to gather for game night. Beds were comfy and all amenities were in good condition. The apartment looks brand new! Loved the shampoo/conditioner/soap dispensers in the shower! Will definitely be back next Christmas. Thanks for the hospitality!"

"Everything was nice and cleaned.Will stay again "

CA $392 total

includes taxes & fees

Jan 23 - Jan 24

"Just as described and fit our needs perfectly. Super clean"

"My family and I stayed with our dog for a few days to see some old friends before going to visit family for Christmas. The space was exactly how it was described and pictured. The setup was easy, attractive, comfy, and extremely well appointed. It was great to have parking and a comfortable place to visit with everyone. The location is very convenient to markets, restaurants, and shopping. The shower is amazing. Kitchen is top notch. We will definitely stay here again!"

"Great place to stay. Parking was great. Nice to have both places and the whole floor!"

"Wesley was super easy to work with. The area is great; the space is great; no complaints at all.Thanks again!"

"First of all, this property was sooooo easy to travel to. I dont mind city driving, but I do get nervous driving downtown. It was so SIMPLE, literally fool proof!! Conveniently located a few blocks from 41 made for a stress-free 15 minute drive to Shedd Aquarium.The house is absolutely beautiful and in a great neighborhood. The property was very secure, neighbors were friendly, and tons of great places within walking distance. Gorgeous original architecture, built ins and stained glass. The...

"The apartment was cozy, clean and comfortable. The owner was easy to reach out to and the location was fantastic. Few mins to bus stops and Blue Line. It was a breeze to check in and out and access it throughout the length of stay. I would return to the same apartment again. "

"Came to see my son graduate bootcamp"

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Other types of properties in Wheeling you may be interested in

"Very cool "

CA $145 total

includes taxes & fees

Jan 26 - Jan 27

"Very conveniently located within the airport, best if you need to transfer at O'Hare. The room is a bit small"

CA $401 total

includes taxes & fees

Jan 24 - Jan 25

"Rey was excellent. "

CA $267 total

includes taxes & fees

Feb 21 - Feb 22

Find out more about Wheeling

Everything you need to know about Wheeling vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Wheeling vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Wheeling vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wheeling vacation rentals we have selected for you start as low as CA $165 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 vacation 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 vacation.

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.

Wheeling Vacation Rental Travel Info

Popular accommodation	Wheeling private vacation homes
Known landmarks	Writers Theatre, Marriott Theatre and Kohl Children's Museum
International airports	Chicago, IL (ORD-O'Hare Intl.) and Chicago, IL (MDW-Midway Intl.)

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Frequently asked questions

Are there vacation rentals in Wheeling?

Yes, we offer vacation rentals close to popular attractions in Wheeling, or you can choose a 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 vacation rentals that Wheeling has to offer?

Luxury Home Away From Your Home: This vacation home rental outside of Wheeling is equipped with a barbecue grill, air-conditioning, and free WiFi to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals will I find in Wheeling?

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

What can I see and do in Wheeling?

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

What are vacation rentals like in Wheeling?

Vacation rentals are privately owned properties you can book for a few days or a quick weekend in Wheeling. Vacation rentals offer extras like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for a family getaway.

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Wheeling Vacation Rentals

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Vacation Rentals in Wheeling

Stunning 3 BR in prime Chicago location

Luxury Home Away From Your Home

Wrigley/Southport Corridor Garden Oasis +parking!

Walking distance to restaurants, shops and Lake Michigan,

Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field

Walk to Wrigley Field/Monthly Discounts Available

3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY

Experience Chicago living near United Center

New Your Home Away From Home! - Near Great Lakes Naval Base!!

Your Next Vacation Home

HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

The Holiday Lake House - 2br 2bth - 50 steps from the beach!

LUXE 3 BR, 2 BA + Hot Tub

Chic, Cozy home, by Blue Line Train Stop + Free parking

NEW LUXURY CONDO WITH PATIO DECK

2 New Construction Suites Same Place

Cozy modern unit w/ easy access to downtown Chi

Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

Hidden East Village Gem

Roxan Corner

Other types of properties in Wheeling you may be interested in

Hampton Inn Chicago-O'Hare International Airport

Hilton Chicago O'Hare Airport

Marriott Chicago O'Hare

Find out more about Wheeling

Wheeling Vacation Rental Travel Info

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Frequently asked questions