Chicago Vacation Rentals - HolidayHomes base64Hash Chicago Vacation Rentals - HolidayHomes

Chicago Vacation Rentals

Browse 5,330 available vacation homes and compared across 9 trusted partners

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Top-Rated Vacation rentals in Chicago

Book the highest-rated Chicago vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

Bed and breakfast Old Town
The Sono Chicago
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Bed and breakfast Bucktown
Ray's Bucktown B&B
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Bed and breakfast Bucktown
Ray's Bucktown B&B
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Bed and breakfast Bucktown
Ray's Bucktown B&B
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Bed and breakfast Wicker Park
Wicker Park Inn
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Bed and breakfast Wicker Park
Wicker Park Inn
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Bed and breakfast Wicker Park
Wicker Park Inn
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Bed and breakfast Wicker Park
Wicker Park Inn
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Bed and breakfast Roscoe Village
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
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Bed and breakfast West Loop
The Publishing House B&B
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Bed and breakfast West Loop
The Publishing House B&B
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Bed and breakfast West Loop
The Publishing House B&B
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Bed and breakfast Roscoe Village
Unique Chicago Penthouse Loft - Amazing Deal & Location
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Bed and breakfast Sheffield Neighbors
Villa D' Citta
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Bed and breakfast Sheffield Neighbors
Villa D' Citta
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Top 15 most Recommended Vacation Rentals in Chicago

Discover your ideal Chicago vacation rental with real-time comparisons of 5,330 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Resort Archer Heights
Resort ∙ 4 guests ∙ 1 bedroom

27 m² Resort

Archer Heights, Chicago, Illinois, United States
This resort in Archer Heights accommodates 127 guests and offers free breakfast for a delightful stay.
from $104
per night
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Bed and breakfast Sheffield & DePaul
Bed and breakfast ∙ 6 guests ∙ 2 bedrooms

Villa D' Citta

Sheffield & DePaul, Chicago, Illinois, United States
This charming bed and breakfast rental in Sheffield & DePaul accommodates 6 guests and features a relaxing hot tub.
from $248
per night
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Bed and breakfast Sheffield Neighbors
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Euro Room

Sheffield Neighbors, Chicago, Illinois, United States
This cozy bed and breakfast rental in Sheffield Neighbors accommodates 2 guests and features a charming fireplace for a warm ambiance.
from $239
per night
(99)
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Bed and breakfast West Loop
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 King Bed (Carmen)

West Loop, Chicago, Illinois, United States
Charming bed and breakfast rental in West Loop accommodates 2 guests and offers a delightful free breakfast for a cozy stay.
from $282
per night
(166)
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Motel Edgewater
Motel ∙ 4 guests ∙ 1 bedroom

Heart O' Chicago Motel

Edgewater, Chicago, Illinois, United States
This Motel in Edgewater accommodates 4 guests and offers convenient parking for a hassle-free stay.
from $101
per night
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Bed and breakfast Boystown
Bed and breakfast ∙ 12 guests ∙ 5 bedrooms

Five bedroom - 3 bath - Sleeps 12

Boystown, Chicago, Illinois, United States
Charming bed and breakfast rental in Boystown accommodates 12 guests and features a kitchen for your convenience.
from $927
per night
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Bed and breakfast Sheffield Neighbors
Bed and breakfast ∙ 6 guests ∙ 1 bedroom

Grand Tuscan Suite

Sheffield Neighbors, Chicago, Illinois, United States
Cozy bed and breakfast rental in Sheffield Neighbors accommodating 6 guests with a charming fireplace for a warm atmosphere.
from $334
per night
(99)
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Motel Washington Heights
2 guests ∙ 1 bedroom

Motel

Washington Heights, Chicago, Illinois, United States
This motel in Washington Heights offers cozy accommodations for 2 guests and features convenient parking for all visitors.
from $87
per night
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Bed and breakfast Sheffield Neighbors
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Caesar's Lair

Sheffield Neighbors, Chicago, Illinois, United States
This charming bed and breakfast rental in Sheffield Neighbors accommodates 2 guests and features a cozy fireplace for a warm atmosphere.
from $241
per night
(99)
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