House holiday rentals in Northwest Side
Find and book unique houses on Airbnb
Top-rated house rentals in Northwest Side
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Northwest Side
House rentals with a pool
Home in Highland Park
4.91 out of 5 average rating, 140 reviews2-Acre Highland Park Retreat with Heated Pool ~ 5*
Home in Munster
5 out of 5 average rating, 8 reviewsMunster hide away
Home
4.86 out of 5 average rating, 29 reviews2Bed+2Bath PentHouse in South Loop
Home
4.94 out of 5 average rating, 34 reviewsGiant Swimming Pool with Whole House!
Home in Bensenville
5 out of 5 average rating, 14 reviewsNew! Arcade+Sauna+Slots+Karaoke+more by O’Hare
Home
4.82 out of 5 average rating, 11 reviewsSchaumburg Oasis with a Pool and Hidden Garden
Home
4.93 out of 5 average rating, 74 reviewsBeautiful Spanish style Home (w/inground pool)
Home
New place to stayOceanFront Resort Studio at Garza Blanca Cancun MX
Weekly house rentals
Home in Chicago
4.89 out of 5 average rating, 47 reviews3BD/2BA Chicago Avondale/Logan Square House
Home in Chicago
5 out of 5 average rating, 63 reviewsNo Cleaning Fee Private Apt. Parking Near Airport
Home
4.88 out of 5 average rating, 90 reviewsA+amazing beauty, entire 2 BR Skokie historic stay
Home
4.82 out of 5 average rating, 62 reviewsLogan Square Portrait Room
Home in Chicago
4.88 out of 5 average rating, 52 reviewsBrand New Spacious Duplex
Home in Oak Park
5 out of 5 average rating, 33 reviewsOak Park - Wine House!
Home in Oak Park
4.95 out of 5 average rating, 19 reviewsVintage Urban Retreat | Oak Park
Home
4.93 out of 5 average rating, 86 reviewsHistoric 1920s bungalow near Logan Square !
Private house rentals
Home in Skokie
4.96 out of 5 average rating, 51 reviewsLuxe Limewash Getaway w/Sun Deck
Home in Chicago
4.98 out of 5 average rating, 91 reviewsEntire first floor in Lincoln Square!
Home in Chicago
4.93 out of 5 average rating, 27 reviewsEntire Home in Historic Logan Square
Home
4.88 out of 5 average rating, 24 reviewsBelmont Heights SFH Oasis
Home in Skokie
4.88 out of 5 average rating, 82 reviewsLuxe-Haus of Love—The 1938 Cape Cod |Heated FLRS |
Home
4.98 out of 5 average rating, 49 reviewsLuxury Home - Pool Tbl/Bar/Patio
Home in Skokie
4.94 out of 5 average rating, 96 reviewsCozy 2 bedroom house/w garage in Skokie
Home in Evanston
4.92 out of 5 average rating, 78 reviews“North Shore Nest” by NU & downtown Chicago
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
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- Family-friendly rentals Northwest Side
- Flat rentals Northwest Side
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- Apartment rentals Northwest Side
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- Monthly Rentals Northwest Side
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