Chicago Luxury Vacation Rentals

Searching for a luxury rental in or near Chicago? We have more than 7309 luxury homes, villas, cottages, and condos that you can rent in Chicago.

Holiday In The Hamptons has a variety of luxury rentals, including vacation homes, apartments, chalets, luxury penthouses, lake homes, beachfront resorts, villas, and many luxury lifestyle options, many in Chicago. Whether you are traveling with families or groups, hosting a get-together, or a cocktail party, we have the perfect place for your travel plans. Our rental properties in Chicago are located in the top places and they come with luxury features throughout the living areas, kitchens, and bedrooms, including private pools, hot tubs, home theatres, amazing views, and plenty of space to relax.