Holiday houses in Near North Side, Chicago
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Top-rated holiday rentals in Near North Side, Chicago
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Near North Side, Chicago holiday rentals
Other great holiday rentals in Near North Side, Chicago
Guest favourite
Guest suite in Lincoln Square
4.94 out of 5 average rating, 180 reviewsLincoln Square In-laws Suite: Private Entrance
Guest favourite
Guest suite in Lincoln Square
4.91 out of 5 average rating, 425 reviewsCozy, Quiet, Garden Getaway!
Superhost
Apartment in Lincoln Park
4.79 out of 5 average rating, 178 reviewsPerfect 1br In Lincoln Park - Steps to Depaul!
Guest favourite
Guest suite in Lincoln Square
4.92 out of 5 average rating, 405 reviewsPrivate Lincoln Square Garden Apt
Guest favourite
Guesthouse in Edgewater
4.95 out of 5 average rating, 373 reviewsCozy Coach House
Guest favourite
Guest suite in West Town
4.96 out of 5 average rating, 311 reviewsAugusta's Garden | Noble Square | Wicker Park
Guest favourite
Loft in Lake View
4.96 out of 5 average rating, 425 reviewsLakeview Loft-Vintage Chicago, Modern Amenities
Guest favourite
Apartment in West Town
4.96 out of 5 average rating, 266 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Quick stats about holiday rentals in Near North Side, Chicago
Total rentals
1.5K properties
Rentals with dedicated workspaces
980 properties have a dedicated workspace
Rentals with a pool
720 properties have a pool
Pet-friendly rentals
750 properties allow pets
Family-friendly rentals
480 properties are a good fit for families
Total number of reviews
52K reviews
Destinations to explore
- Rentals with a patio Near North Side
- Boutique hotel rentals Near North Side
- House rentals Near North Side
- Loft rentals Near North Side
- Rentals with a sauna Near North Side
- Rentals with pools Near North Side
- Townhouse rentals Near North Side
- Family-friendly rentals Near North Side
- Rentals with a fire pit Near North Side
- Hotel rentals Near North Side
- Rentals with a fireplace Near North Side
- Condo rentals Near North Side
- Pet-friendly rentals Near North Side
- Rentals with a hot tub Near North Side
- Kid-friendly rentals Near North Side
- Rentals with beach access Near North Side
- Rentals with outdoor seating Near North Side
- Rentals with a washing machine and dryer Near North Side
- Rentals with breakfast Near North Side
- Rentals with a home theatre Near North Side
- Monthly Rentals Near North Side
- Apartment rentals Near North Side
- Rentals with lake access Near North Side
- Waterfront rentals Near North Side
- Fitness-friendly rentals Near North Side
- Rentals with an EV charger Near North Side
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