50+ Vacation Rentals & Holiday Homes in Kenwood |
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Kenwood Accommodations - Hotels & Rentals

About Kenwood Vacation Rentals

Discover More than 50 Incredible Getaway Rentals Available in Kenwood. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Kenwood.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Kenwood, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Kenwood. The Average Size of Places to Stay Near Kenwood is 733.5 ft², with Prices Averaging US $409 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Kenwood. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Kenwood

Type Count
Holiday Apartments 31
Vacation Homes 10

Use these Quick Filters to Find a Vacation Rental in Kenwood

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Kenwood with Online Reservations.

Weather in Kenwood, IL

View the weather forecast for Kenwood before booking your Kenwood Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Muddy Waters’ House 913 Properties
North Kenwood 660 Properties
Kam Isaiah Israel Congregation 565 Properties
Obama's House 565 Properties
KAM Synagogue 564 Properties
4944 S Woodlawn Ave 562 Properties
Hyde Park Art Center 561 Properties
Elijah Muhammad House 560 Properties
Indian Village 550 Properties
49th Street Beach 539 Properties

Frequently Asked Questions About Kenwood?

What are the top hotels, lake houses & vacation rentals in Kenwood?

We provide an array of great vacation destinations in Kenwood. If you are looking to stay in or around the Kenwood area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Kenwood:

Which hotel, lake house, or vacation rental in Kenwood is best for families?

Searching for a family-friendly getaway in Kenwood? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Kenwood?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 50 in the Kenwood area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Kenwood.

Nearby Neighborhood (3) 
Neighborhood Property Count
East Hyde Park Vacation Rentals in Chicago, Illinois 42
North Kenwood Vacation Rentals in Chicago, Illinois 660
Indian Village Vacation Rentals in Chicago, Illinois 550

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