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Holiday houses in Cook County

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Holiday rentals for every style

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Popular amenities for Cook County holiday rentals

Kitchen
Wi-Fi
Pool
Free parking on premises
Air conditioning

Other great holiday rentals in Cook County

Superhost
Private room in Chicago
4.82 out of 5 average rating, 34 reviews

HydeParkB, UC, Chinatown, NavyPier, freeparking

ChloéRating, 5 stars5 days ago
Vraiment super, ambiance hôtel. Le logement était d’une propreté impeccable, toutes commodités: sèche cheveux, climatisation, ventilateur, cotons tiges, serviettes, bouteilles d’eau… franchement je n’ai rien n’a redire. Le calme dépend évidemment des voyageurs présents dans le Airbnb, nous n’avons rencontré aucun soucis. Merci pour ce séjour parfait!
Private room in Chicago
4.86 out of 5 average rating, 43 reviews

23rd Pl 2D

Jack G.Rating, 5 stars4 days ago
I came to Chicago for a demanding conference. I was not interested in spending as much as $200 a night for a room I would only spend 6 to 8 hours in a day. By contrast, Ming’s Guest House on W 23rd Place was perfect. It was clean, quiet and uncongested; it offered peace & tranquility. Ming was the ideal hostess. She was amazingly responsive to inquiries sent by text. All questions were answered in a super reliable and professional manner. The Guest House surpassed my expectations. The bathroom was clean and accommodating. The same goes for my room. Would I come again? I would. Ming gets a 10 out of 10.
Private room in Chicago
4.73 out of 5 average rating, 40 reviews

Bees Knees - Room 3

BernardoRating, 5 stars2 weeks ago
I really enjoyed my stay at this place and would definitely recommend it, especially for the value. It’s conveniently located near bus stops and small markets, which made getting around and grabbing essentials very easy. The host was always very responsive and helpful, which made the whole experience smoother. The apartment is well-equipped with many utensils—there were plates, glasses, a cooking area that worked well for meals, and even an iron and ironing board. It’s also relatively quiet, which was great for resting. There are a few minor details that could be improved, like a couple of broken light bulbs, some marks on the bathroom walls, and a creaky, uneven floor. I also missed having a few hooks in the bedroom. However, none of these were major issues or detracted from the overall quality of the stay. I would not recommend it for people with mobility issues due to the steep staircase, but all in all, a great place with excellent value and a very helpful host. Would stay again.
Guest favourite
Private room in Chicago
4.88 out of 5 average rating, 48 reviews

Yellow Room - South Shore Bungalow

GavinRating, 5 stars2 weeks ago
What a lovely place to stay. Lady Delia showed us her turtles and had a beautiful cat. She was very friendly and talkative. She drove us to get bus passes when we didn’t know where to get them. Jeffrey jump was a convenient bus to get from her place to the city very quickly. The bathroom had the window creaked open which made it smell like the coast in the mornings. The house is a historic bungalow which gave it a very different look and feel from what I’m used to. Spent some beautiful morning strolls along the neighborhood and got to see the beautiful architecture in the city; overall was worth what we paid.
Guest favourite
Private room in Oak Park
5 out of 5 average rating, 9 reviews

DT Oak Park LUXE Private BR C | Queen Bed Sleeps 2

YanitRating, 5 stars3 weeks ago
I had a great stay at this place! The location was absolutely perfect—close to grocery stores and everything I needed was easily accessible. The bedroom was definitely my favorite part: super comfy bed and a spacious closet that fit all my luggage with ease. Everything was clean and well-maintained, which made the stay even more enjoyable. Parking is on the street and not included, but there was plenty of space and could park right in front whenever I needed which was a huge plus. Would definitely stay here again!
Private room in Chicago
4.74 out of 5 average rating, 143 reviews

Hyde Park/UC Newly Renovated Private Room #3

AssainaRating, 5 stars2 weeks ago
Andy is an excellent host. He is very professional, attentive, and communicative. He made sure that my stay went smoothly. The apartment was very clean, organized, and ideally located. I really enjoyed my stay and highly recommend staying at his apartment when you visit Chicago.
Guest favourite
Private room in Berwyn
4.94 out of 5 average rating, 62 reviews

Nice cozy room

AlexRating, 5 stars2 weeks ago
La atención y el lugar son muy acogedores, una amplia recámara en los suburbios de Chicago, definitivamente lo que mejoró la experiencia es la comunicación, Dolores se esforzó en todo momento por cubrir las necesidades durante la estancia!
Guest favourite
Private room in Chicago
4.95 out of 5 average rating, 63 reviews

near festivals & united center

LindseyRating, 5 stars1 week ago
Danielle was an excellent host and the place was exactly as expected. The perfect landing spot for a weekend in Chicago!
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