Find Vacation Rentals in Near North Side

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Popular Near North Side Vacation Rentals

Find the perfect Near North Side vacation rental

Bed and breakfast Near North Side
from $312 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Caesar's Lair

4.6
Excellent(99 ratings)
Near North Side, Chicago, Illinois, United States
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Details
Bed and breakfast Near North Side
from $340 per night
Bed and breakfast ∙ 5 guests ∙ 1 bedroom

Florencia Suite

4.6
Excellent(99 ratings)
Near North Side, Chicago, Illinois, United States
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Bed and breakfast Near North Side
from $308 per night
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

Capone's Cantina

4.6
Excellent(99 ratings)
Near North Side, Chicago, Illinois, United States
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Bed and breakfast Near North Side
from $327 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Venetian Suite

4.6
Excellent(99 ratings)
Near North Side, Chicago, Illinois, United States
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Bed and breakfast Near North Side
from $408 per night
Bed and breakfast ∙ 6 guests ∙ 1 bedroom

Grand Tuscan Suite

4.6
Excellent(99 ratings)
Near North Side, Chicago, Illinois, United States
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Details
Bed and breakfast Near North Side
from $353 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Suite, 1 King Bed (Sinclair)

4.9
Outstanding(166 ratings)
Near North Side, Chicago, Illinois, United States
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Details
Bed and breakfast Near North Side
from $353 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Suite, 1 King Bed (Everleigh)

4.9
Outstanding(166 ratings)
Near North Side, Chicago, Illinois, United States
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Details
Bed and breakfast Near North Side
from $380 per night
Bed and breakfast ∙ 5 guests ∙ 1 bedroom

Milan Suite

4.6
Excellent(99 ratings)
Near North Side, Chicago, Illinois, United States
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Details
Bed and breakfast Near North Side
from $251 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Euro Room

4.6
Excellent(99 ratings)
Near North Side, Chicago, Illinois, United States
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Pet-Friendly Homes and Apartments

Bed and breakfast  Near North Side
from $273 per night
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

East Room (Lower Level)

4.9
Outstanding(340 ratings)
Near North Side, Chicago, Illinois, United States
Pet-friendly
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Details
Bed and breakfast  Near North Side
from $260 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Cuckoo Room (Second Floor)

4.9
Outstanding(340 ratings)
Near North Side, Chicago, Illinois, United States
Pet-friendly
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Details
Bed and breakfast  Near North Side
from $260 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Woodpecker (Second Floor)

4.9
Outstanding(340 ratings)
Near North Side, Chicago, Illinois, United States
Pet-friendly
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Vacation rentals with a balcony

Motel  Near North Side
from $177 per night
Motel ∙ 4 guests ∙ 1 bedroom

30 m² Motel

4.4
Very good(928 ratings)
Near North Side, Chicago, Illinois, United States
Balcony
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Details
Motel  Near North Side
from $158 per night
Motel ∙ 2 guests ∙ 1 bedroom

14 m² Motel

4.4
Very good(928 ratings)
Near North Side, Chicago, Illinois, United States
Balcony
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Details
Bed and breakfast  Near North Side
from $242 per night
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

Deluxe Suite, 2 Queen Beds

4.9
Outstanding(443 ratings)
Near North Side, Chicago, Illinois, United States
Balcony
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Vacation homes and rentals with a yard

Bed and breakfast  Near North Side
from $231 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 King Bed (Schiller)

4.4
Very good(238 ratings)
Near North Side, Chicago, Illinois, United States
Yard
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Details
Bed and breakfast  Near North Side
from $266 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 King Bed (Hoyne)

4.4
Very good(238 ratings)
Near North Side, Chicago, Illinois, United States
Yard
HomeToGo
Details
Bed and breakfast  Near North Side
from $280 per night
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

Exclusive Apartment, 1 Queen Bed with Sofa bed (Garden)

4.4
Very good(238 ratings)
Near North Side, Chicago, Illinois, United States
Yard
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Frequently Asked Questions

How much does a night in a vacation rental cost in Near North Side on average?

Accommodation in Near North Side cost from $130 per night.

Can I see all vacation rentals that are available in Near North Side?

On tripping.com, you will find 4,600 available vacation rental offers in Near North Side.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Near North Side

Looking for the perfect vacation rental for your Near North Side getaway? Tripping.com’s got you covered. Whether you’re seeking a vacation home, cabin rental or cottage, Near North Side offers 487 affordable vacation home rentals to choose from, with far more amenities, space and comforts than the average hotel room. Select from 380 properties with high-speed WiFi Internet, 145 full with jacuzzi and pool, and homes complete with outdoor patio, great for entertaining with guests. Whatever your needs, find the perfect home rental that best matches your accommodation style and budget. For travelers planning for an extended stay, long-term lodging and corporate rentals only cost an average of $25 a month. Save hundreds with affordable vacation rentals on Tripping.com and, in many cases, book directly online so you’re all set to go. Near North Side has 487 gorgeous homes with 150 pet-friendly rentals to choose from, perfect for your dog or cat. Check out our vacation rental listings now to get the latest deals, and book the right vacation home rental for you and the whole family. Feel at home wherever you are and experience an unforgettable vacation with Tripping.com. Search properties from 5 vacation rental sites in Near North Side where the top providers in that area are HomeAway, HRS Holidays, and Expedia. There are 137 HomeAway rentals, 129 HRS Holidays short term rentals and 86 Expedia vacation rentals.

Popular Day Trips Near Near North Side

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