Wheeling Holiday Rentals

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Wheeling holiday rentals

Smart TV, books

Chic Suite/Mins to L Train /Laundry/Free Parking

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.6 out of 10, Exceptional, (63 reviews)
"Comfortable bed, spacious rooms and clean."
United States
Michael W.
The price is HK$719
HK$1,809 total
includes taxes & fees
19 May - 20 May
Chic Suite/Mins to L Train /Laundry/Free Parking
Exterior

Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
The price is HK$1,104
HK$3,449 total
includes taxes & fees
27 May - 28 May
Modern 3BR Apartment Near North Ave Shops
1 bedroom, iron/ironing board, travel cot, WiFi

Charming Sunlit 1BR Apartment

Charming Sunlit 1BR Apartment
Irving Park
9.0 out of 10, Wonderful, (15 reviews)
"Host was very attentive and answered all of our questions. It was very cozy and exactly as pictured."
United States
Brandon M.
Charming Sunlit 1BR Apartment
Smart TV

F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
Barrington
9.8 out of 10, Exceptional, (9 reviews)
"Very nice little spot... Host was absolutely wonderful!!! Definitely stay here again!"
United States
Adam B.
The price is HK$745
HK$1,342 total
includes taxes & fees
14 May - 15 May
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
Exterior detail

Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (80 reviews)
"Had a lovely stay in a beautiful home! The setting is very secluded and quiet."
United States
Kyle M.
The price is HK$768
HK$1,519 total
includes taxes & fees
14 May - 15 May
Master qtr close to nature & easy urban facilities
TV, offices

Homey 1BR Space Apartment

Homey 1BR Space Apartment
Lincoln Square
9.4 out of 10, Exceptional, (18 reviews)
"Love the location right in Lincoln Square. "
United States
Ticia B.
Homey 1BR Space Apartment
Fridge, microwave, oven, stovetop

Navy Family home -Near Lake 4BR Hot Tub

Navy Family home -Near Lake 4BR Hot Tub
Gages Lake
9.6 out of 10, Exceptional, (13 reviews)
"Nice location for our family attending our daughter's graduation from Navy Basic at Great Lakes. "
United States
Judson S.
The price is HK$1,816
HK$5,336 total
includes taxes & fees
13 May - 14 May
Navy Family home -Near Lake 4BR Hot Tub
Interior

Tiny Home Retreat with hot tub

Tiny Home Retreat with hot tub
Lake Villa
9.0 out of 10, Wonderful, (4 reviews)
"Amazing stay, great host! "
United States
Aaron L.
The price is HK$1,058
HK$2,432 total
includes taxes & fees
13 May - 14 May
Tiny Home Retreat with hot tub
TV, offices

Great Layout – Spacious 2BR Apt

Great Layout – Spacious 2BR Apt
Rogers Park
9.2 out of 10, Wonderful, (11 reviews)
"Clean, comfortable, and would definitely stay again!"
United States
KM W.
Great Layout – Spacious 2BR Apt
1 bedroom, iron/ironing board, WiFi, bed sheets

1BR Unit w/ 2 Comfy Beds

1BR Unit w/ 2 Comfy Beds
Lakeview
9.8 out of 10, Exceptional, (6 reviews)
"Property was great. Stayed for 2 nights and you have everything you need within walking distance. Great communication and easy to navigate. "
United States
Ethan S.
1BR Unit w/ 2 Comfy Beds
Exterior detail

Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
9.8 out of 10, Exceptional, (72 reviews)
"We had a great stay! The area was peaceful and felt safe. "
United States
Yoselin V.
The price is HK$1,057
HK$2,572 total
includes taxes & fees
13 May - 14 May
Quaint Bungalow, near Great Lakes Naval Base
Iron/ironing board, travel cot, WiFi, bed sheets

Sunlit Studio with City Charm

Sunlit Studio with City Charm
Rogers Park
8.0 out of 10, Very good, (11 reviews)
"Host was extremely welcoming and accommodating. They went out of their way to assure me that they were but a call away if there was anything we needed."
United States
Renee W.
The price is HK$665
HK$1,442 total
includes taxes & fees
13 May - 14 May
Sunlit Studio with City Charm
TV, offices

Vibrant 1BR Apartment

Vibrant 1BR Apartment
Lakeview
9.8 out of 10, Exceptional, (7 reviews)
"Great place. Host was very informative. "
United States
Cheryl S.
The price is HK$783
HK$1,678 total
includes taxes & fees
13 May - 14 May
Vibrant 1BR Apartment
Interior

Comfortable 2BR Chicago Apt

Comfortable 2BR Chicago Apt
Albany Park
9.6 out of 10, Exceptional, (7 reviews)
"Perfect location for our trip. Very functional and comfortable. "
United States
Michael
The price is HK$979
HK$2,044 total
includes taxes & fees
13 May - 14 May
Comfortable 2BR Chicago Apt
Dining

Lovely 1BR Apartment in Lakeview

Lovely 1BR Apartment in Lakeview
Lakeview
8.6 out of 10, Excellent, (9 reviews)
"Great apartment, great location, and excellent host."
United States
Benjamin N.
Lovely 1BR Apartment in Lakeview
Exterior

Cozy Train Vibes + Rare Parking x3

Cozy Train Vibes + Rare Parking x3
North Center
10.0 out of 10, Exceptional, (18 reviews)
"It was a great spot to be, we loved it! The hosts were super responsive and helped resolve all our questions. Would absolutely stay there again if needed :) "
United States
Jenna P.
The price is HK$1,516
HK$3,558 total
includes taxes & fees
13 May - 14 May
Cozy Train Vibes + Rare Parking x3
Smart TV, fireplace, offices

PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard

PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
Arlington Heights
9.0 out of 10, Wonderful, (6 reviews)
"Host was very responsive. Location was perfect for what we needed.Really liked having a garage for the car."
United States
Katie C.
The price is HK$1,866
HK$3,998 total
includes taxes & fees
18 May - 19 May
PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
Smart TV

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
8.0 out of 10, Very good, (26 reviews)
"Was a very nice stay and the host was very helpful and got very quick responses "
United States
Eduardo
The price is HK$1,163
HK$2,341 total
includes taxes & fees
13 May - 14 May
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
2 bedrooms, iron/ironing board, free WiFi, bed sheets

Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (74 reviews)
"Nice, clean, safe house."
United States
Adrienne P.
The price is HK$1,127
HK$2,698 total
includes taxes & fees
20 May - 21 May
Cozy, Comfortable and Convenient apartment. Close to everything!
TV, offices

Cozy & Furnished 2BR Unit

Cozy & Furnished 2BR Unit
Lincoln Square
9.2 out of 10, Wonderful, (20 reviews)
"Very cozy, amenities in great condition."
United States
Kaitlin T.
Cozy & Furnished 2BR Unit
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

Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

6/10 Okay
"Property is maintained well. Room was fine, nothing s I ecial but comfortable. I don't know the relationship with the restaurant, but that seems lacking. I had breakfast, I had to ask for cream and sugar for my coffee, not offered; had to ask for salt and pepper. Not offered, no refill on coffee, had to ask... wondering if Management is being cheap or trying to control waste. Disservice to the wait staff, although not trained properly.. for was ok, not outstanding."
Sonja 1-night trip
Posted 2 hours ago
Holiday Inn Chicago O'Hare – Rosemont by IHG

Find out more about Wheeling

Search for holiday rentals in Wheeling on Expedia! You can easily find your home rentals, villas, holiday apartments in Wheeling using one of the methods below:

  • View our selection of featured holiday rentals in Wheeling
  • Use the map to find apartments and other holiday homes in the Wheeling neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Wheeling while they last

Look no further and take a look at our great range of rental properties in Wheeling!

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 of 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.