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Compare 457 Vacation Homes in Kenilworth with updated reviews, rates, and availability.

Belmont House, Classy & Chic/walk to Wrigley Field

9.4 out of 10, Exceptional, (41)
"Perfect location. Home was very comfortable and inviting. Beds and mattresses were heavenly. We thoroughly enjoyed our stay. "
Belmont House, Classy & Chic/walk to Wrigley Field

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

9.4 out of 10, Exceptional, (85)
"We rented this house so that two families could stay for the weekend in Chicago to celebrate our kids engagement. The house is great, it's pet friendly, it's in a great location, the garage is very useful for parking cars, etc. However, you really, really need to read the owner's rules. If you read the listing's first part "great place for your friends and family gathering", "
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Eddy House, Roscoe Village Hideaway

10.0 out of 10, Exceptional, (5)
"Great house . "
Eddy House, Roscoe Village Hideaway

Your Next Vacation Home

9.8 out of 10, Exceptional, (30)
"Very clean, extremely nice home. "
The price is SAR 563
SAR 1,069 total
includes taxes & fees
28 Jan - 29 Jan
Your Next Vacation Home

Breathtaking home close to Schaumburg, Chicago

9.8 out of 10, Exceptional, (46)
"Fit our whole family nicely."
Breathtaking home close to Schaumburg, Chicago

Entire house 1 city block from Wrigley Field.

9.8 out of 10, Exceptional, (19)
"Very comfortable home close to Wrigley and to restaurants, coffee shop and shopping."
Entire house 1 city block from Wrigley Field.

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (44)
"Great location.Description was on point.Accommodations were a bet. "
The price is SAR 409
SAR 728 total
includes taxes & fees
14 Jan - 15 Jan
Master qtr close to nature & easy urban facilities

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

Roxan Corner

8.4 out of 10, Very Good, (30)
"Came to see my son graduate bootcamp"
Roxan Corner

Cheery 2+bedroom home with free parking on premises

9.8 out of 10, Exceptional, (33)
"Third time staying at this property. Great property and location. "
Cheery 2+bedroom home with free parking on premises

Riverfront Libertyville Retreat w/ Outdoor Kitchen

9.0 out of 10, Wonderful, (18)
"Great place! Plenty of room. It was convenient and a nice community. It was cold while we were there and were not able to use outdoor kitchen.Our son was graduating from Navy Bootcamp and it was a very short drive to graduation. Plenty of restaurants close by."
Riverfront Libertyville Retreat w/ Outdoor Kitchen

Stunning 4-bedroom 4-bath building in Wicker Park! + Parking

Stunning 4-bedroom 4-bath building in Wicker Park! + Parking

4 Bedroom, 2 Full Bath. Centrally Located. Near O'Hare Airport and attractions

9.4 out of 10, Exceptional, (8)
"We had a mini cousin reunion with family who drove in from different states. No one here has a house big enough to have all of us, so this was the perfect option. The house was lovely, neighborhood very nice, easy to get to, and the host was gracious making us feel like we were all at home. I’d give it 10/5 stars if I could!"
4 Bedroom, 2 Full Bath. Centrally Located. Near O'Hare Airport and attractions

Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

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

10.0 out of 10, Exceptional, (121)
"We had a nice stay. The property was clean and spacious. The kitchen was fully equipped with modern cooking accessories. It was convenient to Lincoln Park, Wrigleyville, and downtown. "
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

10.0 out of 10, Exceptional, (162)
"Beautiful home & location. Excellent and fast communication with the owner. Everything was as expected, if not better!"
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

10.0 out of 10, Exceptional, (35)
"Stayed for a bachelor party. Nice neighborhood, short walk to wrigley with bars along the way to stop at. Only annoying thing was parking. While there is 3 spots (2 car garage, plus 1 on the small apron in front of the garage) you can not park more than 1 bigger vehicle there so we had to use the parking garage nearby. Luckily it was only 25/day. "
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

Elegant 3BD Chalet! 🌲15min to ORD/Train 2 Dwntwn!

10.0 out of 10, Exceptional, (11)
"It was a great house with needed amenities and lots of space. Great location not far from downtown. Host was great to communicate with."
Elegant 3BD Chalet! 🌲15min to ORD/Train 2 Dwntwn!

Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym

10.0 out of 10, Exceptional, (3)
"Upscale tri level home, easy location to get to and Uber from. House is very well designed and set up for a larger family group. 4 nice bedrooms with really nice bathrooms and a small workout area. Living room and kitchen open up to a back deck area with lower level sitting spaces. Great place to stay for concerts or just an easy location to visit the pier or soldier field or Wrigley or white Sox. We enjoyed our week. "
Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym
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 property types in Kenilworth

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (654)
"Excellent property. Everything was top notch. "
The price is SAR 412
SAR 593 total
includes taxes & fees
14 Jan - 15 Jan
Sentral Michigan Avenue

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (416)
"Beautiful Hotel with lots of amenities and entertainment in a walking distance "
The price is SAR 422
SAR 495 total
includes taxes & fees
30 Jan - 31 Jan
Sonder South Wabash

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (240)
"Wonderful experience. Easy in and out access. Very comfortable "
The price is SAR 189
SAR 222 total
includes taxes & fees
21 Jan - 22 Jan
Sonder Market Hall
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.