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The best holiday rentals in Illinois

Check out our pick of great holiday rentals in Illinois

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Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
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Housed in a historic building, the recently renovated Riverboat Suites offers accommodation with a garden and free WiFi. The property has city views and is 25 km from Diamond Jo Casino and 400 metres from Belvedere Mansion. The bed and breakfast has a sun terrace and a hot tub. We had a wonderful stay at Nate's property. At arrival we felt right at home. Super easy check-in. Bed was very comfortable. Breakfast was great and Nate was so welcoming and helpful. We hope to be back!

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9.3
Superb
221 reviews
Price from
US$125.28
per night

Set in Galena, within 23 km of Diamond Jo Casino and 2.3 km of Galena-Jo Daviess County History Museum, Cloran Mansion Bed & Breakfast provides accommodation with a garden as well as free private parking for guests who drive. The property has garden views and is 3.2 km from Belvedere Mansion and 3.5 km from Galena Historic District. The accommodation offers a hot tub, free WiFi throughout the property and family rooms. Paul and his staff keep their property very clean and up to date. Our Tower Room that we stayed in was very comfortable and had a lot of fun and unique pieces to it. The food was also SPECTACULAR. I also told Paul that it was my wife and I’s 5th anniversary, and he had a cake and sparkling grape juice (also a baby-moon) ready for when we arrived!

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9.7
Exceptional
120 reviews
Price from
US$155
per night

Located in Galena, 21 km from Diamond Jo Casino, Belle Aire Mansion Guest House provides accommodation with free WiFi and free private parking. Housed in a building dating from 19th century, this bed and breakfast is 3.6 km from J Dubuque Monument and 4 km from Galena-Jo Daviess County History Museum. The bed and breakfast features family rooms. Comfortable and homey. Hosts were awesome! Everything was clean.

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9
Superb
182 reviews
Price from
US$110
per night

The spacious holiday home with a terrace and quiet street views features 3 bedrooms, a living room, a flat-screen TV, an equipped kitchen with an oven and a microwave, and 1 bathroom with a bath. Towels and bed linen are featured in the holiday home. The property has an outdoor dining area. Easy access to a nice property in a good location. The hosts were amazing and easy to communicate with. Noemi was so nice and decorated the house for the holiday- it was so cool! We had a blast!

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9.4
Superb
128 reviews
Price from
US$135
per night

The Sono Chicago is located in The Old Town neighborhood of Chicago. Lincoln Park Zoo is only 1.2 km away. Parking is free with permit provided by The Sono Chicago.

The rooms are fitted with a flat-screen TV with premium cable channels. Each room has an en suite bathroom with a large shower. Perfect way to see the life of the neighborhood from the inside. Staff, room, bed, breakfast - everything is great!

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9.3
Superb
322 reviews
Price from
US$130.80
per night

Ray's Bucktown Bed and Breakfast provides a sauna and free private parking, and is within 4.9 km of Lincoln Park Zoo and 5.1 km of Wrigley Field. Featuring a garden, the 3-star bed and breakfast has air-conditioned rooms with free WiFi, each with a private bathroom. The bed and breakfast features family rooms as well as facilities for disabled guests. Everything. The atmosphere, the staff, everything was incredible. I only wished I had stayed longer. Ashlee was very helpful and accommodating. I was upgraded to the room with a view and would highly recommend staying there.

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9.3
Superb
174 reviews
Price from
US$153.19
per night

Located in the heart of downtown Chicago, just 3 blocks away from the Magnificent Mile, this self-catering apartment features a balcony with iconic views of the city. Free WiFi access is available.

Floor-to-ceiling windows frame the fireplace in the 2-bedroom apartment at The Penthouse at Grand Plaza. Along with a fully-equipped kitchen and 3 full bathrooms, the apartment includes a dining area, laundry facilities and 3 separate balconies. The apartment was spacious, clean and comfortable. Walking distance to Navy pier, Millennium Park, shopping, donuts, and having Jewel O grocery store below was more than convenient. Many delicious restaurants close by Frontera Grill being a highlight. The instructions for arrival, parking, and departure were easy to understand and made for a smooth stay at this beautiful place with superb views. Definitely recommend parking at the Grand as parking around town is at a premium. We will absolutely stay here again on our next visit to the windy city💕🌆

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9.3
Superb
101 reviews
Price from
US$158.12
per night

The recently renovated A secluded bedroom with a private full bathroom is set in Chicago, near 57th Street Beach and Museum of Science and Industry - Chicago. Among the facilities at this property are full-day security and luggage storage space, along with free WiFi throughout the property. The property is non-smoking and is located 7.1 km from Guaranteed Rate Field. The welcome and the kindness of the host, the comfort.

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9.1
Superb
20 reviews

Set within 1.3 km of Union Station and 1.7 km of Willis Tower, Sage Modern Apartments Near Union Park in West Loop offers rooms with air conditioning and a private bathroom in Chicago. Guests staying at this apartment have access to a balcony. Private parking can be arranged at an extra charge. We walked in, and it was first class all the way. Clean and comfortable with everything I needed at my fingertips. Charlie was attentive and available for any request. The rooms were floor to ceiling amazing views. Bathrooms immaculate and showers had hot, high water pressure that felt soothing. Charlie stocked our fridge as a treat, with breakfast goodies for a kitchen that is fully equipped. The coffee maker was fantastic and made our mornings pleasurable. Can't wait to visit Chicago again, and when I do, it will be with Cloud9.

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9
Superb
28 reviews
Price from
US$190.65
per night

The spacious holiday home is located on the ground floor and is fitted with 6 bedrooms, a flat-screen TV with cable channels and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a toaster. A private entrance leads guests into the holiday home, where they can enjoy some wine or champagne and chocolates or cookies. There is also a seating area and a fireplace. Everything was fantastic! The spaces were well furnished, there was lots of natural light, and the bedrooms were super comfortable. The bathrooms and kitchen were top notch and we couldn't have had a more wonderful time staying there!

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9.8
Exceptional
9 reviews
Price from
US$647.19
per night

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