The 10 best cottages in Chicago, US | Booking.com
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Cottages in Chicago

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The best cottages in Chicago

Check out our selection of great cottages in Chicago

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Historic Home with Outdoor Hot Tub Near Downtown in Public Transportation Hub

Chicago

A recently renovated vacation home, Historic Home with Outdoor Hot Tub Near Downtown in Public Transportation Hub offers accommodations in Chicago.

A
Ashley
From
United States
This is truly a home away from home. We felt at ease the entire stay and even though we had a jam-packed trip, coming back to the house felt like coming home. The neighborhood is great for walking, and feels extremely safe. There are fantastic coffee shops and restaurants all throughout the neighborhood, and the street parking is plentiful, which makes staying in the city so much easier. I had exactly 30 minutes to myself during the trip, and while everyone else rested, I got in the hot tub and really recharged for the rest of our evening. It was cool outside and perfect in the tub. I cannot more highly recommend this home, and I can't thank Andrea enough. The house is historic and beautiful, and very clean. The beds are so comfortable, and having more than one bathroom is such a bonus. We ended up needing to use the dryer, and it's so nice to have laundry facilities when you accidentally end up with a wet shoe and socks! There's a fireplace and seating for hanging out inside when it's chilly, and it's super cozy. There's a Keurig for coffee and Andrea even offered to get us milk for coffee, but we opted to walk down to the local spots and soak in the neighborhood. I've said a lot but I still feel like I'm not capturing how great the property really is. If you've found this one, stop scrolling!
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 8 reviews
Price from
$450
1 night, 2 adults
Check availability

Designer Themed 4 Bedroom in Best Location with Patio and Fireplace

Near North Side, Chicago

Offering a garden, Designer Themed 4 Bedroom in Best Location with Patio and Fireplace offers accommodations in Chicago.

S
Strand
From
United States
This was our first attempt at a non-hotel location. I was surprised how much we appreciated the home's amenities away from home. Amenities like; multiple bathrooms, full kitchen, private off-street parking and a pleasant neighborhood.
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 29 reviews
Price from
$419
1 night, 2 adults
Check availability

4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome

Near North Side, Chicago

A 19-minute walk from Oak Street Beach in Chicago, 4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome provides accommodations with access to spa facilities and fitness room.

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 5 reviews
Price from
$499
1 night, 2 adults
Check availability

Lakefront Rooftop Parking

Chicago

Providing a garden, Lakefront Rooftop Parking features accommodations in Chicago. This beachfront property offers access to a balcony, free private parking, and free Wifi.

D
Demetris
From
United States
Very nice, the owner was very helpful and on time with my needs, felt like home❤️
Scored out of 10, guest rating 8.2
Very Good - What previous guests thought, 6 reviews
Price from
$319.50
1 night, 2 adults
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A Home Away from Home!

Chicago

A Home Away from Home! is located in Chicago, just 4.7 miles from Museum of Science and Industry - Chicago and 9.4 miles from Guaranteed Rate Field.

U
Usman
From
United States
5 stars Wonderful Stay! I had an amazing experience staying at this Airbnb! The home was exactly as described clean, cozy, and thoughtfully decorated. The host was incredibly responsive and made the check-in process super smooth. The neighborhood was quiet and safe, with great local restaurants and shops nearby. I especially appreciated the little touches, like fresh towels, snacks, and local recommendations
Scored out of 10, guest rating 7.3
Good - What previous guests thought, 7 reviews
Price from
$107.67
1 night, 2 adults
Check availability

The Avondale Guesthouse

Chicago

The Avondale Guesthouse is located in Chicago, just 2.8 miles from Wrigley Field and 3.6 miles from Lincoln Park Zoo.

K
Kam
From
United States
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!
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 135 reviews
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Chicago Treasure 4 Bed Getaway

West Town, Chicago

Chicago Treasure 4 Bed Getaway offers accommodations in Chicago, 1.9 miles from Water Tower Chicago and 2.1 miles from 360 Chicago. The air-conditioned accommodation is 1.7 miles from United Center.

Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 6 reviews
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The Logandale: HUGE Mid-Century Home, sleeps 15

Chicago

The Logandale: HUGE Mid-Century Home, sleeps 15 offers accommodations in Chicago, 4.8 miles from Lincoln Park Zoo and 6 miles from United Center.

L
Lisa
From
United States
Excellent location! The house was comfy and very clean, loved the coffee bar. Danny the host was awesome!
Scored out of 10, guest rating 10.0
Exceptional - What previous guests thought, 5 reviews
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Beautifully Renovated House 10 mins from Downtown

Bronzeville, Chicago

Beautifully Renovated House 10 mins from Downtown offers accommodations in Chicago, 1.5 miles from Oakwood Beach and 1.7 miles from Guaranteed Rate Field.

N
Nermin
From
United States
Excellent location, beautiful, clean and spacious house with all amenities needed. Fantastic communication and friendly service, would love to stay here again.
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 7 reviews
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Spacious Row Home next Transit near Downtown w Parking

Chicago

Spacious Row Home next Transit near Downtown w Parking offers accommodations in Chicago, 2.1 miles from United Center and 3.9 miles from Union Station.

D
Denisse
From
United States
Love this property, easy access, house was perfect for a Family of 10, was clean and have everything you need.
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 15 reviews
Check availability
All cottages in Chicago

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Cottages are perfect for travelers who enjoy feeling cozy and independent in the countryside. Usually small, traditionally built houses, cottages are spread across one or two floors – making them great for families or vacations with a little more privacy.

Most booked cottages in Chicago and surrounding area in the past month

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Enjoy breakfast in Chicago and nearby

  • Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 7 reviews

    Historic luxury Townhouse in Downtown Chicago is located in Chicago, just a 15-minute walk from Shops at Northbridge and 1.4 miles from Millennium Station.

  • Spacious 3-Bed West Loop Townhouse, 1 Car Garage townhouse is located in Chicago, just a 17-minute walk from Willis Tower and 1.4 miles from CIBC Theatre.

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 2 reviews

    Just a 13-minute walk from Water Tower Chicago and 0.6 miles from 360 Chicago, Gold coast villa with free parking garage sleeps 10 features accommodations in Chicago with a garden.

  • Scored out of 10, guest rating 8.8
    Excellent - What previous guests thought, 5 reviews

    Just a 13-minute walk from Water Tower Chicago and 0.6 miles from 360 Chicago, Luxurious Gold Coast 4BR 4-Story Villa with Parking Sleeps 12 Guests features accommodations in Chicago with a garden.

  • Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 5 reviews

    A 19-minute walk from Oak Street Beach in Chicago, 4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome provides accommodations with access to spa facilities and fitness room.

  • Located in Chicago, this holiday home is 0.7 mi from Lincoln Park Zoo and Downtown Chicago. Offering free private parking, the holiday home is 0.9 mi from 360 Chicago.

  • Scored out of 10, guest rating 9.0
    Wonderful - What previous guests thought, 1 review

    Old Town 3bd 3ba Coach House, Garage Parking Incl is located in Chicago, just 1.6 miles from Water Tower Chicago and 1.6 miles from 360 Chicago.

  • Just a 13-minute walk from North Avenue Beach and 0.7 miles from Lincoln Park Zoo, Top 1 Rated 4BR Lincoln Park House - King Bed features accommodations in Chicago, with a fitness center and a garden.

These cottages in Chicago and nearby have options with free cancellation

  • Scored out of 10, guest rating 1.0
    Bad - What previous guests thought, 1 review

    Large Condo with Outdoor Deck in Historic Chicago District home is located in Chicago, just 1.9 miles from Water Tower Chicago and 2 miles from 360 Chicago.

  • Charming & Bright Multilevel Townhome with Parking offers accommodations in Chicago, 1.1 miles from Lincoln Park Zoo and 2 miles from Water Tower Chicago.

  • Cute and Cozy Chicago Modern Condo

    Chicago
    Free cancellation options available

    Cute and Cozy Chicago Modern Condo is located in Chicago, just 2.4 miles from Water Tower Chicago and 2.5 miles from Union Station. The air-conditioned accommodation is 1.5 miles from United Center.

  • Wicker Park 6bd 4ba, Steps from CTA, Parking Incl home offers accommodations in Chicago, 2.3 miles from United Center and 2.6 miles from Water Tower Chicago.

  • Wicker Park 4bd 3ba, Steps from CTA, Parking Incl home offers accommodations in Chicago, 2.6 miles from Water Tower Chicago and 2.7 miles from Union Station.

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 2 reviews

    The Village Inn by Dakota Gal Digs is located in Chicago, just 1.8 miles from North Avenue Beach and 1.7 miles from Lincoln Park Zoo.

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 2 reviews

    Perfect Location Across from Park & Train Station is located in Chicago, just 2.9 miles from United Center and 4.6 miles from Union Station.

  • Spacious 5-BR House near Transit w Parking

    Chicago
    Free cancellation options available
    Scored out of 10, guest rating 9.3
    Wonderful - What previous guests thought, 14 reviews

    Offering a garden, Spacious 5-BR House near Transit w Parking offers accommodations in Chicago. This property offers access to a terrace, free private parking, and free Wifi.

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