Wheeling Holiday Rentals

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Holiday Rentals in Wheeling

WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, 188 reviews
"ITS A VERY NICE AND UPBEAT ESTABLISHMENT.......I ENJOYED THE STAY ONLY THING I DIDNT LIKE WAS THERE HOUSE KEEPING SCHEDULE BUT OTHER THAN THAT ITS A NICE QUIET LOCATION WITH NICE PEOPLE"
The price is NZ$154
includes taxes & fees
5 Jun - 6 Jun
WoodSpring Suites Chicago Addison
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, 106 reviews
"The host communicated well. The area was busy but felt safe. I felt it was expensive for the location. Very clean."
Luxury Home Away From Your Home
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, 157 reviews
"Great property and Ross is a wonderful host. Even recommended dinner spots Hope to stay here again"
Walking distance to restaurants, shops and Lake Michigan,
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Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.2 out of 10, Wonderful, 9 reviews
"Great location with two master suites with king beds. Breakfast buffet was good. Next time I will request first floor as there is no elevator."
The price is NZ$337
includes taxes & fees
5 Jun - 6 Jun
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, 39 reviews
"Well renovated, nice bathroom."
Wrigley/Southport Corridor Garden Oasis +parking!
4-Bedroom Penthouse w/ 2 Large Balconies & Rooftop
10.0 out of 10, Exceptional, 22 reviews
"We were in town for our son’s wedding and this was the perfect location for our group. Apartment was as advertised and the host was very responsive and helpful. The rooftop provided a perfect place for some pre-wedding groom/best man photos as well."
4-Bedroom Penthouse w/ 2 Large Balconies & Rooftop
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
9.6 out of 10, Exceptional, 8 reviews
"Great unit! Spacious and clean. We were able to have the best family mini vacay sharing tons of laughs and memories. I believe it is family owned, which is a bonus for us. We even crossed paths with the grandmother who was very kind and accommodating. The only downside was that the neighborhood looked a bit rough in the harsh light of day. However, we only encountered polite neighbors and an adorable doggo next door."
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
Chic Suite/Mins to L Train /Laundry/Free Parking
9.4 out of 10, Exceptional, 18 reviews
"The manager had unbelievable communication. He has his phone with him constantly and responds immediately. It's a good walking neighborhood lots of sidewalks and pleasant surroundings. The condo itself is exceptionally clean. For the price in that neighborhood it is a very good value."
Chic Suite/Mins to L Train /Laundry/Free Parking
national historic home near downtown airports no parties no events
9.4 out of 10, Exceptional, 20 reviews
"It was an amazing property so quiet and calm area lovely host super great with communication and answering any questions I had"
The price is NZ$558
includes taxes & fees
5 Jun - 6 Jun
national historic home near downtown airports no parties no events
Cozy modern unit w/ easy access to downtown Chi
9.6 out of 10, Exceptional, 18 reviews
"It’s really confortable clean and accesible easy"
Cozy modern unit w/ easy access to downtown Chi
Stay in “STYLE” Apartment, close to CHI downtown
9.8 out of 10, Exceptional, 62 reviews
"Really fun neighborhood with unexpected street fair & very cute apartment."
Stay in “STYLE” Apartment, close to CHI downtown
NEW LUXURY CONDO WITH PATIO DECK
10.0 out of 10, Exceptional, 126 reviews
"It will be interesting to see how the balcony in the living room will be incorporated into the final apartment…."
NEW LUXURY CONDO WITH PATIO DECK
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
9.8 out of 10, Exceptional, 25 reviews
"Such a great house and the owner was very responsive. Thank you!"
The price is NZ$2,327
includes taxes & fees
5 Jun - 6 Jun
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
LUXE 3 BR, 2 BA + Hot Tub
8.8 out of 10, Excellent, 10 reviews
"Our team had a one day conference in Chicago. Although it was near the highway it wasn't very loud. Decent neighborhood and the good part is that it was near the highway. Lower level bed is uncomfortable, no other way to say that. I still give it 5-stars as it is as advertised. Communication with owner was timely."
The price is NZ$641
includes taxes & fees
5 Jun - 6 Jun
LUXE 3 BR, 2 BA + Hot Tub
3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY
10.0 out of 10, Exceptional, 57 reviews
"Thank you so much for the lovely stay. Although I was unable to attend, my husband, son, daughter, and son-in-law were able to stay. They all made mention of how clean everything was, how everything was comfortable and well appointed. It was easy to check in and check out. I think beds could have been a little bit softer (all four commented on that), but your place is beautiful! Would also recommend ceiling fans or floor fans in each room to cut out noise and for better temperature. Would...
3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY
Hidden East Village Gem
9.6 out of 10, Exceptional, 21 reviews
"Property was clean and spacious which was perfect for our family of 4. The neighbor was cute and we felt safe being there. Free street parking, though spaces were some times limited. Overall, we were happy with our stay."
Hidden East Village Gem
Stunning 3 BR in prime Chicago location
9.8 out of 10, Exceptional, 45 reviews
"This place is in a great location in Chicago! Plenty of space and a fun main area, brought me back to when i lived in Chicago - would definitely book this place again!!"
Stunning 3 BR in prime Chicago location
Bright Garden Studio
9.0 out of 10, Wonderful, 4 reviews
"I'm a seminary student, and I came into town for an intensive class. So, I was really only in the space in the evenings, but it was comfy. The location is amazing!!! The studio apartment was decently clean. The projector is VERY cool. There were a few details I could not find instructions for, like where to take the garbage out when I was on my way out. But I left a message for the owner and they were good about it. I would stay again. Recommend."
Bright Garden Studio
Game room/King Bed /Wi-Fi/Deck + Fire Pit
10.0 out of 10, Exceptional, 14 reviews
"Host was amazing with communication, check in was seemless house was clean and a great experience for me and my family would high recommend"
The price is NZ$795
includes taxes & fees
23 Jun - 24 Jun
Game room/King Bed /Wi-Fi/Deck + Fire Pit
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
10.0 out of 10, Exceptional, 147 reviews
"We had a wonderful time!!"
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
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See all available properties in Wheeling
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.

Other types of properties in Wheeling you may be interested in

Marriott Chicago O'Hare
3.5 star property
8.2 out of 10, Very good, 1,012 reviews
"The stay was nice. Beautiful pool side view. The only downside was that I couldn’t connect to the internet because I didn’t book directly through the hotel. Bummer. "
The price is NZ$302
includes taxes & fees
1 Jul - 2 Jul
Marriott Chicago O'Hare
SureStay Plus Hotel by Best Western Chicago Lombard
2.5 star property
8.8 out of 10, Excellent, 1,556 reviews
"Have to remember that it's not a best Western. Breakfast was mediocre and the beds were hard. Pillows were quite small. Although that furniture showed where the room was clean and comfortable."
The price is NZ$145
includes taxes & fees
5 Jun - 6 Jun
SureStay Plus Hotel by Best Western Chicago Lombard
Best Western At O'Hare
2.5 star property
7.4 out of 10, Good, 1,875 reviews
"The transportation was quite efficient "
The price is NZ$218
includes taxes & fees
1 Jul - 2 Jul
Best Western At O'Hare
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Wheeling holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Wheeling. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Wheeling. Seeing all the best attractions is bound to make you fall in love with Wheeling. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Wheeling short-term rentals, that won’t be hard to do.

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?

Luxury Home Away From Your Home: This holiday home rental outside of Wheeling has air conditioning and cable TV to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals will I find in Wheeling?

Choose from 5 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.

Recent reviews of Wheeling properties
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