Chicago Vacation Rentals - HolidayHomes base64Hash Chicago Vacation Rentals - HolidayHomes

Chicago Vacation Rentals

Browse 5,575 available vacation homes and compared across 10 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 Fulton Market
The Publishing House B&B
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Bed and breakfast Fulton Market
The Publishing House B&B
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Bed and breakfast Fulton Market
The Publishing House B&B
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Bed and breakfast Fulton Market
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 & DePaul
Villa D' Citta
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Bed and breakfast Sheffield & DePaul
Villa D' Citta
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Bed and breakfast Sheffield & DePaul
Villa D' Citta
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Bed and breakfast Sheffield & DePaul
Villa D' Citta
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Bed and breakfast Magnolia Glen
House 5863 - Chicago Bed and Breakfast
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Bed and breakfast Magnolia Glen
House 5863 - Chicago Bed and Breakfast
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Bed and breakfast Magnolia Glen
House 5863 - Chicago Bed and Breakfast
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Bed and breakfast Magnolia Glen
House 5863 - Chicago Bed and Breakfast
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Bed and breakfast Old Town
The Sono Chicago
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Bed and breakfast Old Town
The Sono Chicago
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Top 15 most Recommended Vacation Rentals in Chicago

Discover your ideal Chicago vacation rental with real-time comparisons of 5,575 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Bed and breakfast Boystown
Bed and breakfast ∙ 12 guests ∙ 5 bedrooms

B&B with 5 rooms for 12 persons

Boystown, Chicago, Illinois, United States
Charming bed and breakfast rental in Boystown accommodates 12 guests and features a kitchen for your convenience.
from $867
per night
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Bed and breakfast West Ridge
Bed and breakfast ∙ 3 guests ∙ 2 bedrooms

B&B with 2 rooms for 3 persons

West Ridge, Chicago, Illinois, United States
This charming bed and breakfast rental in West Ridge accommodates 3 guests and features a fully equipped kitchen for your convenience.
from $71
per night
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Bed and breakfast Bucktown
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Family-oriented wonderful bed and breakfast with terrace & garden | Suitable for remote work | Pets are welcome

Bucktown, Chicago, Illinois, United States
Charming bed and breakfast rental in Bucktown with a capacity for 2 featuring a cozy kitchen and free breakfast.
from $208
per night
(349)
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Bed and breakfast Fulton Market
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast for 2 persons

Fulton Market, Chicago, Illinois, United States
Cozy bed and breakfast rental in West Loop accommodating 2 guests with complimentary breakfast for a delightful stay.
from $319
per night
(171)
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Bed and breakfast East Village
Bed and breakfast ∙ 16 guests ∙ 8 bedrooms

B&B with garden | Perfect for remote work

East Village, Chicago, Illinois, United States
Charming bed and breakfast rental in East Village accommodates 16 guests and features a relaxing spa for ultimate comfort.
from $4,033
per night
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Bed and breakfast Sheffield & DePaul
Bed and breakfast ∙ 5 guests ∙ 1 bedroom

Bed and breakfast with terrace, barbecue & yard

Sheffield & DePaul, Chicago, Illinois, United States
This cozy bed and breakfast rental in Sheffield Neighbors accommodates 5 guests and features a charming fireplace for a warm ambiance.
from $438
per night
(100)
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Motel Washington Heights
Motel ∙ 2 guests ∙ 1 bedroom

Pleasant motel for 2 persons

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 $89
per night
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Bed and breakfast Old Town
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast with patio

Old Town, Chicago, Illinois, United States
This charming bed and breakfast rental in Old Town accommodates 2 guests and features a cozy fireplace for a warm atmosphere.
from $205
per night
(452)
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Motel River North
Motel ∙ 4 guests ∙ 1 bedroom

Motel | Near Magnificent Mile

River North, Chicago, Illinois, United States
This River North motel accommodates 4 guests and offers free breakfast for a convenient stay.
from $257
per night
(1001)
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