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The best holiday rentals in Illinois

Check out our pick of great holiday rentals in Illinois

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Review score

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. Location was great-could walk to everything! Perfect girl’s weekend atmosphere with private garden near patios for chatting with food/beverages. Rooms cozy and comfortable. Nate, hotel manager, super nice and full of good recommendations

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9.2
Superb
227 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. Amazing host, wonderful house and delicious breakfast!

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9.7
Exceptional
121 reviews
Price from
US$139
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
186 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. The location was perfect, it was also very clean and the owner was really very attentive, I would recommend it

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9.4
Superb
130 reviews
Price from
US$157.50
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. It’s located in a residential neighborhood so it’s very peaceful and perfect to walk around during this time of the year. Everything thing is clean and very well decorated. I came with my sister for one night and wished we could have stayed longer. Highly recommended!

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9.3
Superb
318 reviews
Price from
US$132
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. location was amazing, breakfast was great.

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9.3
Superb
177 reviews
Price from
US$171.19
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
102 reviews
Price from
US$162.84
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. Easy check in, really comfortable place, and overall great surroundings for a walk, be it through the University's campus grounds or to the lake. Getting to downtown is fairly easy.

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9.1
Superb
20 reviews

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$793.80
per night

The spacious holiday home is equipped with 6 bedrooms, 5 bathrooms, bed linen, towels, a flat-screen TV with streaming services, a fully equipped kitchen, and a terrace with garden views. The property has an outdoor dining area. Excellent location, beautiful, clean and spacious house with all amenities needed. Fantastic communication and friendly service, would love to stay here again.

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9.2
Superb
7 reviews
Price from
US$405
per night

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