Photo by Marc Jacobs
Kenwood holiday rentals
We found 90 holiday rentals — enter your dates for availability
Discover a selection of 5 flats and other holiday rentals in Kenwood that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday homes have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a fireplace. You're sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.
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Find the best place to stay - Kenwood
Gorgeous N. Kenwood/Hyde Park
Sleeps 11 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Spacious 4 Bedroom (5 queen beds) 2 Bath in the kenwood neighborhood
Sleeps 10 · 4 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
41 reviews(41 reviews)
Charming 3BR Chicago Apt in Prime Location
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
10 reviews(10 reviews)
Penthouse Condo in Chicago featuring Zero Gravity Massage Chair
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
18 reviews(18 reviews)
1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier
Sleeps 6 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
54 reviews(54 reviews)
Modern & Spacious Stay in Historic Bronzeville
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of holiday home accommodation in Kenwood?
Based on our data, apartments are the most desirable type of holiday home in Kenwood. But naturally, everyone’s idea of the perfect stay is bound to be different. Stayz has holiday homes with every shape, size and budget in mind, and we’ll help you locate your perfect match.
How much does it cost to rent a holiday home in Kenwood?
Different things determine what you’ll pay for a holiday home in Kenwood, including the time of year, length of stay and property type. Still, all Stayz homes have something in common — exceptional value. Simply enter your travel dates to find your perfect fit.
How much does it cost to rent a beach house in Kenwood?
Prices for beach houses in Kenwood will vary depending on the size and style of the property and time of year you’re travelling. Simply enter your travel dates into Stayz and the number of guests to view your holiday home options and prices. From there you can use the filters to narrow down your search by amenities, nearby activities, ratings and more.
Are there pet-friendly holiday homes in Kenwood?
Pack up a suitcase for your puppy dog because Kenwood has 11 properties that throw out the welcome mat to pets. Let your four-legged buddy join in on the family trip at one of our pet-friendly holiday homes on Stayz. Simply enter your travel dates and destination, then check our “Pets allowed” filter box.
Can I rent a house with a pool in Kenwood?
Pack your swimwear and inflatable swan, because there are two houses with a private pool in Kenwood. Unwind at one of these sought-after holiday homes and make every day a pool day. Simply enter your travel dates into Stayz, then use the “pool” filter to find a place to make a splash!
What are popular home amenities in Kenwood?
When it comes to home amenities that guests look for in Kenwood, a firepit, a lake view and nearby museums rank the highest. With Stayz holiday homes, you’ll have options to fit your style and taste, whether you’re going away with your partner, your friends or even pets.
Are there large group holiday homes in Kenwood?
With two Kenwood properties that can accommodate a group of five or more people, you can invite a few extra pals or family members along. Whether you’re planning a casual gathering or a birthday party, we’ll help you book a comfortable space to match the occasion.
Are there holiday homes in Kenwood that welcome kids?
Kenwood has 11 family-friendly holiday homes to choose from. And securing a stay that welcomes youngsters is super easy with our “Properties good for families” filter. As well as having the whole place to yourselves, you’ll also enjoy access to amenities and perks like extra bedrooms, private pools and yards.
What are the top attractions for families in Kenwood?
There are tons of exciting things to do and see with the family in Kenwood, such as:
- Navy Pier
- Chicago Riverwalk
- Shedd Aquarium
Are there one-bedroom holiday homes in Kenwood?
Yes, Kenwood has two one-bedroom homes on offer. Often situated in popular areas thanks to their compact size, a one-bedroom property is perfect if you’re getting away with a pal or your partner. And with home comforts such as full kitchens and more privacy than a standard hotel, you’ll be able to kick back while exploring this awesome destination.
Can I find two-bedroom holiday homes in Kenwood?
Take your pick of four two-bedroom properties in Kenwood. Give your little ones the second room or maybe fill it with a couple of your besties. There’s ample space for whoever’s lucky enough to be coming along for the ride.
Are there holiday homes with WiFi in Kenwood?
Take your pick of nine holiday homes with WiFi in Kenwood. If you want to disconnect from daily life on your break, but still need to be connected to the web, these getaways are just what you need. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Kenwood?
Pick your travel dates and then use the filter tool to see holiday homes with air conditioning in Kenwood on Stayz. With 10 air-conditioned properties available, you can look forward to a comfy and cool stay.
How old do you have to be to rent a holiday home in Kenwood?
It’s advisable to check with the Kenwood holiday home you’d like on Stayz as age restrictions differ. However, generally it’s 16, 18 or 21.
How long can I rent a holiday home in Kenwood for?
The amount of time you can rent a Kenwood holiday home for depends on each property. Simply put in your dates of travel to see available options that offer extended stays. They have all you require to make your extended trip more comfortable like kitchens and yards. Some holiday homes may also offer weekly or monthly discounts, so you can stick around for longer for less.