Holiday lettings & accommodation in Chicago - HolidayHomes base64Hash Holiday lettings & accommodation in Chicago - HolidayHomes

Holiday lettings & accommodation in Chicago

Find 5,575 available offers from 10 partners

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Top-Rated Lettings and Properties in Chicago

Book Holiday Letting Offers with the Highest User Rating

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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Bed and breakfast Old Town
The Sono Chicago
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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 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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Top 15 Recommended holiday lettings in Chicago

Find your perfect vacation rental in Chicago from just £53 per night!

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
A charming bed and breakfast rental in West Ridge with capacity for three guests and a well-equipped kitchen for your convenience.
from £54
per night
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Bed and breakfast Boystown
Bed and breakfast ∙ 12 guests ∙ 5 bedrooms

B&B with 5 rooms for 12 persons

Boystown, Chicago, Illinois, United States
This charming bed and breakfast rental in Boystown accommodates 12 guests and features a lovely balcony for relaxation.
from £652
per night
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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
This charming bed and breakfast rental in East Village accommodates up to 16 guests and features a lovely garden for relaxation.
from £3,031
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
This charming Bed and Breakfast rental in Bucktown accommodates 2 guests and features a lovely garden for relaxation.
from £157
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
This charming Bed and breakfast rental in West Loop accommodates 2 guests and offers a delightful free breakfast each morning.
from £240
per night
(171)
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Bed and breakfast Humboldt Park
Bed and breakfast ∙ 7 guests ∙ 3 bedrooms

Bed and breakfast | Perfect for remote work

Humboldt Park, Chicago, Illinois, United States
This charming bed and breakfast rental in Humboldt Park accommodates 7 guests and features convenient on-site parking.
from £374
per night
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Bed and breakfast Sheffield & DePaul
Bed and breakfast ∙ 5 guests ∙ 1 bedroom

Bed and breakfast with garden, terrace & barbecue

Sheffield & DePaul, Chicago, Illinois, United States
This charming bed and breakfast rental in Sheffield Neighbors accommodates 5 guests and features a lovely garden for relaxation.
from £330
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 cosy motel in Washington Heights offers comfortable accommodation for 2 guests with convenient parking available on-site.
from £67
per night
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Bed and breakfast Old Town
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast with terrace

Old Town, Chicago, Illinois, United States
This charming bed and breakfast rental in Old Town accommodates 2 guests and features a cosy fireplace for added comfort.
from £154
per night
(452)
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