Wheeling Vacation Rentals

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Vacation Rentals in Wheeling

Wrigley/Southport Corridor Garden Oasis +parking!

9.8 out of 10, Exceptional, (67)
"Very clean and comfortable place!"
Wrigley/Southport Corridor Garden Oasis +parking!

Stunning 3 BR in prime Chicago location

9.8 out of 10, Exceptional, (83)
"Very close to the train. Good location "
Stunning 3 BR in prime Chicago location

Stunning / Spacious 6BD Home + garage - Bucktown!

9.4 out of 10, Exceptional, (28)
"I invited 5 guest to join me in Chicago for a birthday trip. This home is perfectly located between MDW and ORD. We had no trouble getting to our activities, great restaurants, downtown, or quick stores (Target, CVS, etc). The layout of the home is perfect with rooms and bathrooms on each level. The homeowner is also a wonderful communicator, great at responding. We had no trouble getting a hold of them prior to the trip or during the trip. Highly recommend! "
Stunning / Spacious 6BD Home + garage - Bucktown!

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

9.4 out of 10, Exceptional, (38)
"I'd stay again, it was nice. Only issue was the upstairs neighbor must have been doing remodeling because the entire day was filled with hammers, drills, stomping etc. But all in all I enjoyed it."
Chic, Cozy home, by Blue Line Train Stop + Free parking

Luxury Home Away From Your Home

9.0 out of 10, Wonderful, (116)
"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!"
Luxury Home Away From Your Home

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (174)
"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."
Walking distance to restaurants, shops and Lake Michigan,

Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!

10.0 out of 10, Exceptional, (120)
"We had an amazing time, and this home was a large part of why we enjoyed Chicago so much! The hosts were great, and very responsive to all of our questions! The home was spacious and warm. The perfect location, so close to the train so we could travel back and forth to downtown. The kitchen has a great space for cooking, what a great stove. The ping pong/billiards table was a hit! We would definitely stay here again! "
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!

Stay in “STYLE” Apartment, close to CHI downtown

9.8 out of 10, Exceptional, (72)
"This is the 3rd time I’ve booked this Ukrainian Village apartment. It’s comfortable and has everything needed for visits into the city. "
Stay in “STYLE” Apartment, close to CHI downtown

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (152)
"We had a great stay, location was great, very clean, beautifully remodeled, the bathroom felt like a 5 star hotel with all the upgrades they've done. The first night the refrigerator stopped working, they immediately went over to try to fix it but were unsuccessful, they offered to purchase ice for us and by the next day they had purchased and installed a new refrigerator. Overall, we had a great experience and would definitely stay here again. "
NEW LUXURY CONDO WITH PATIO DECK

Hidden East Village Gem

9.6 out of 10, Exceptional, (29)
"Perfect spot for a family. Visiting for husband’s conference. Great neighborhood and easy to get to all tourist attractions. Highly recommend. All our needs were anticipated. "
Hidden East Village Gem

Quaint Bungalow, near Great Lakes Naval Base

10.0 out of 10, Exceptional, (56)
"Got to stay in this wonderful home while visiting my son and his family. I loved it!"
The price is CA $194
CA $451 total
includes taxes & fees
Dec 24 - Dec 25
Quaint Bungalow, near Great Lakes Naval Base

Walking distance to restaurants, shops and Lake Michigan,

9.8 out of 10, Exceptional, (194)
"The apartment is beautifully decorated and updated. Ross, the host gave us a welcome tour and everything was clearly explained. Beds are comfortable and rooms are spacious. We were relieved our rental minivan (just barely) fit in the garage! We did the kitchen wasn't as well equipped as we would have liked, but we were cooking a Thanksgiving meal which may have been a bit ambitious. The meal turned out well and we enjoyed our stay immensely!"
Walking distance to restaurants, shops and Lake Michigan,

PET FRIENDLY! Unique Converted Storefront Stay - Great Neighborhood! by AllSet Turnover

9.4 out of 10, Exceptional, (26)
"Nice open space with large bedrooms. Quiet and clean! Perfect location to walk to local restaurants and shops "
PET FRIENDLY! Unique Converted Storefront Stay - Great Neighborhood! by AllSet Turnover

Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

10.0 out of 10, Exceptional, (32)
"We had a great time staying here for a family trip. Plenty of space for games, cooking, sleeping, talking. We only used a fraction of what was available. When we had trouble figuring out heating system, host was very responsive. "
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

Historic Oak Park Residence

2.0 star property
9.4 out of 10, Exceptional, (6)
"This was quite a charming home. The access to public transportation was great. One mile walk or drive to parking garage. We ventured into the city every day but could have easily stayed in Oak Park."
The price is CA $193
CA $353 total
includes taxes & fees
Jan 7 - Jan 8, 2025
Historic Oak Park Residence

Walk to Wrigley Field/Monthly Discounts Available

9.6 out of 10, Exceptional, (128)
"Clean and great location "
Walk to Wrigley Field/Monthly Discounts Available

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

10.0 out of 10, Exceptional, (166)
"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...
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field

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

9.6 out of 10, Exceptional, (35)
"Had a great stay! Thank you!"
The price is CA $130
CA $286 total
includes taxes & fees
Jan 4 - Jan 5, 2025
Chic Suite/Mins to L Train /Laundry/Free Parking

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

10.0 out of 10, Exceptional, (38)
"So clean and welcoming with a terrific location just steps from a lovely beach! The property was very clean, comfortable and well-kept, and looked like the kitchen and bathrooms had been recently re-done (loved the tile and fixtures!). The shower in the master is a spa-like experience! Great communication with the owner, too. So happy with our stay, and we would absolutely look forward to saying here again!"
The Holiday Lake House - 2br 2bth - 50 steps from the beach!

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

9.4 out of 10, Exceptional, (30)
"The spacious, well-maintained home was perfect for our group. The bedrooms were roomy, and the living areas provided plenty of space to relax and enjoy time together. The fully equipped kitchen made meal prep easy. A highlight was the neighboring estate with horses. The children loved it! The outdoor spaces were ideal for relaxation, with patios for morning coffee. Overall, this rental was the perfect setting for a memorable getaway. "
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
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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Other types of properties in Wheeling you may be interested in

Hampton Inn Chicago-O'Hare International Airport

2.5 star property
9.2 out of 10, Wonderful, (1568)
"Great front desk staff, pleasant stay for what it is"
The price is CA $142
CA $162 total
includes taxes & fees
Dec 24 - Dec 25
Hampton Inn Chicago-O'Hare International Airport

Chicago Getaway Hostel

2.0 star property
8.8 out of 10, Excellent, (1007)
"Very easy and clean. Everyone was super nice. I felt very safe and comfortable. Great stay "
The price is CA $57
CA $76 total
includes taxes & fees
Jan 5 - Jan 6, 2025
Chicago Getaway Hostel

Marriott Chicago O'Hare

3.5 star property
8.4 out of 10, Very good, (1008)
"After a particular harrowing trip the staff here at the Marriott were warm and welcoming. I felt cared for and safe. The room was clean and pleasant and I was able to rest peacefully."
The price is CA $194
CA $228 total
includes taxes & fees
Dec 27 - Dec 28
Marriott Chicago 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.

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?

Stunning / Spacious 6BD Home + garage - Bucktown!: This vacation home rental outside of Wheeling offers a selection of games, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Wheeling?

Choose from 3 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 Randhurst Village.

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.