Kenilworth Vacation Rentals

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Check prices for these dates

In two weeks
Jan 2 - Jan 4
In two months
Feb 13 - Feb 15
In three months
Mar 13 - Mar 15
In four months
Apr 10 - Apr 12

Our top choices for Kenilworth vacation rentals

Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1009)
"This place made a great landing spot for a holiday weekend w family. Clean, great location, loved the holiday decorations and indoor pool / outside hot tub. Will stay again! "
United States
Deidre
The price is ￥18,409
￥26,182 total
includes taxes & fees
Dec 21 - Dec 22
Sentral Michigan Avenue
Free WiFi, bed sheets
Chicago luxury home suites

Chicago luxury home suites

Chicago luxury home suites
2.0 star property
Downtown Chicago
7.4 out of 10, Good, (3)
"Do not book. This is a scam you will be asking to zelle a several hundred dollar security deposit after paying in full and before check in. You’ll receive sketchy FaceTime audio calls and messages from several different numbers requesting this. "
United States
Brooke
The price is ￥16,406
￥19,258 total
includes taxes & fees
Dec 17 - Dec 18
Chicago luxury home suites
Front of property - evening/night
Level Chicago – Old Town

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (401)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
Business center
Kasa River North Chicago

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Interior
Gold Coast Living: Modern Studio Unit

Gold Coast Living: Modern Studio Unit

Gold Coast Living: Modern Studio Unit
Downtown Chicago
10.0 out of 10, Exceptional, (5)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is ￥10,751
￥25,788 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Gold Coast Living: Modern Studio Unit
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space
Downtown Chicago
9.6 out of 10, Exceptional, (14)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is ￥12,309
￥31,508 total
includes taxes & fees
Dec 18 - Dec 19
Twice as Nice: Chic 2BR Stay with Style & Space
TV, offices
Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Amazing accommodation"
United States
Jiri N.
The price is ￥20,567
￥56,635 total
includes taxes & fees
Dec 22 - Dec 23
Modern West Loop Gem-City Views & Prime Location 4
Fridge, microwave, oven, stovetop
West Loop Living – Bright 1BR

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (4)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
The price is ￥9,816
￥26,251 total
includes taxes & fees
Jan 4 - Jan 5, 2026
West Loop Living – Bright 1BR
Fridge, microwave, oven, stovetop
Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is ￥9,816
￥26,251 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Sun-Drenched 1BR Apartment
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop

Stylish 1BR in West Loop

Stylish 1BR in West Loop
Downtown Chicago
10.0 out of 10, Exceptional, (10)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
United States
Jacob D.
The price is ￥9,816
￥26,251 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Stylish 1BR in West Loop
1 bedroom, WiFi, bed sheets
1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is ￥9,816
￥26,251 total
includes taxes & fees
Jan 1 - Jan 2, 2026
1BR Modern Luxe Apt with In-Unit Laundry
Interior
Your Chicago get Away

Your Chicago get Away

Your Chicago get Away
Downtown Chicago
8.4 out of 10, Very Good, (8)
"Clean, simple space close to the parks at the waterfront (Millennium, Grant, etc) and several spots for coffee. A bit of an odd building location (it's in a dorm tower with a laundry space next door! Not noisy tho) but easy to access at all hours, nice view as pictured."
United States
Pip M.
The price is ￥28,164
￥60,551 total
includes taxes & fees
Dec 18 - Dec 19
Your Chicago get Away
Fridge, microwave, oven, stovetop
The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home
Downtown Chicago
8.4 out of 10, Very Good, (5)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is ￥9,816
￥26,251 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The One: A 1BR Stay That Feels Like Home
Interior
Downtown Chicago Stay with Free In & Out Parking 3

Downtown Chicago Stay with Free In & Out Parking 3

Downtown Chicago Stay with Free In & Out Parking 3
2.0 star property
Downtown Chicago
The price is ￥18,697
￥53,943 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Downtown Chicago Stay with Free In & Out Parking 3
Fridge, microwave, oven, stovetop
River North Rooftop With In and Out Parking 1

River North Rooftop With In and Out Parking 1

River North Rooftop With In and Out Parking 1
Downtown Chicago
9.0 out of 10, Wonderful, (2)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
The price is ￥22,281
￥57,980 total
includes taxes & fees
Dec 27 - Dec 28
River North Rooftop With In and Out Parking 1
TV, offices
South Loop Rooftop With In & Out Parking 1

South Loop Rooftop With In & Out Parking 1

South Loop Rooftop With In & Out Parking 1
Downtown Chicago
9.0 out of 10, Wonderful, (2)
"We loved the property! It was well kept, clean, with a seamless check in and check out process! I wish the parking garage would have been closer but otherwise everything was great! Shout out to the host for his promptness with all my questions! I would recommend this place if they are looking for a place to stay! "
United States
Bridney K.
The price is ￥16,204
￥49,716 total
includes taxes & fees
Jan 8 - Jan 9, 2026
South Loop Rooftop With In & Out Parking 1
Business Apartment, City View | Private kitchen | Fridge, microwave, oven, stovetop
ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments
2.0 star property
Near North Side
10.0 out of 10, Exceptional, (8)
"We loved at our stay at this property. It was one of the best stays we have had on vacation."
United States
Javeria
The price is ￥133,462
￥189,409 total
includes taxes & fees
Dec 18 - Dec 19
ENVITAE Hotel 4 Bedroom Luxury Apartments
Fridge, microwave, oven, stovetop
Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveler
The price is ￥9,816
￥26,251 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Sleek 1BR Apt w/ Laundry
TV, offices
Complete 1BR Home Sum

Complete 1BR Home Sum

Complete 1BR Home Sum
Downtown Chicago
The price is ￥9,816
￥26,251 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Complete 1BR Home Sum
4 bedrooms, iron/ironing board, travel crib, WiFi
Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"The host communicated everything very well. The short videos sent giving info about all the things you'd need to know were super helpful!"
United States
Laurie A.
Modern West Loop Gem-City Views & Prime Location 3
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 Kenilworth Hotel Reviews

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

10/10 Excellent
"The staff was so friendly and helpful and the hotel was beautiful"
Julianne 2-night trip
Posted 4 hours ago
Palmer House a Hilton Hotel

Find out more about Kenilworth

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

  • View our selection of featured holiday rentals in Kenilworth
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  • Enter your travel dates to view the best deals on holiday rentals in Kenilworth while they last

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

Frequently asked questions

Can I find vacation rentals in Kenilworth?

Yes, there are vacation rentals near the most popular points of interest in Kenilworth, or you can choose a secluded option if you want a relaxing place to stay. Kenilworth is known for its lake views and shopping. Make sure you have time to check out the restaurants and sporting events during your trip.

What's the top vacation rental that Kenilworth has to offer?

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars: This vacation home rental near Kenilworth is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease 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. You can relax into your vacation with a private yard and a selection of games.

What’s there to see and do in Kenilworth?

Lake Michigan and Kenilworth Beach are a couple of lovely local spots to get outside and enjoy nature. Wrigley Field and Michigan Avenue are other popular places to visit in the area.

What’s a vacation rental in Kenilworth like?

A vacation rental is a private property where you can stay for several days or longer in Kenilworth. Vacation rentals offer extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you the enjoyment of 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 popular option for a small group gathering.