
Holiday houses in Northwest Side
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Northwest Side
Guests agree: these stays are highly rated for location, cleanliness and more.
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Popular amenities for Northwest Side holiday rentals
Other great holiday rentals in Northwest Side
Superhost

Home in Chicago
4.93 out of 5 average rating, 40 reviewsFamily Friendly Duplex/9 min from MDW/Free Parking
JoannaRating, 5 stars2 weeks ago
Came for c2e2 with my friends and it was perfect for all of us! Would recommend 💗💗
Superhost

Guest suite in Plainfield
4.86 out of 5 average rating, 78 reviewsRelaxing Suite with Independent Entrance
CindyRating, 5 stars2 weeks ago
Maria’s place was great! Easy access to the Airbnb & the yard was a bonus for our two dogs. Lots of little touches that made the stay pleasant; coffee, water, snacks were all appreciated. The bed was very comfortable too! I would definitely stay again when in the area.
Superhost

Apartment in Chicago
4.86 out of 5 average rating, 42 reviewsElegant 4Bedroom with Free Parking in Albany Park
MatthewRating, 5 stars2 months ago
Wonderful stay as always, thank you so much!
Superhost

Apartment in Chicago
4.63 out of 5 average rating, 24 reviewsCity Gem: Stylish 3BR for Urban Explorers
AnnikaRating, 5 stars1 month ago
Peaceful, felt like home, very spacious and comfortable
Superhost

Home in Aurora
5 out of 5 average rating, 24 reviewsEvergreen Retreat
AlyssaRating, 5 stars2 days ago
The location was great for a family reunion. So many small details were thought of to make the stay so smooth. Will definitely stay again.
Superhost

Home in Lombard
5 out of 5 average rating, 25 reviewsSpacious Home in Chicago Suburbs
JenniferRating, 5 stars3 weeks ago
It was great! The house was lovely and looked newly renovated. It was much roomier than I expected. The beds were very comfortable.
Superhost

Home in Chicago
5 out of 5 average rating, 21 reviewsComfy Home Away From Home
ZakiRating, 5 stars2 weeks ago
This home completely transformed our view of Chicago. We arrived a little nervous, but the moment we walked in, we were greeted by a space that was warm, welcoming, and absolutely stunning. Every detail was thoughtfully curated, from the sleek kitchen to the plush pillows on the sectional. The kitchen is modern and fully stocked, perfect for cooking and gathering. The living room is beautifully styled and cozy, and the bedrooms felt like luxurious retreats with spa-like linens and calming decor. The basement lounge was a standout with its oversized sectional and elegant bar area, so perfect for relaxing after a long day. We especially loved the little reading nook with the blue chairs. Every corner of this home radiates peace and intentionality. It truly felt like a sanctuary. We left feeling inspired, rested, and already planning our return.
Superhost

Apartment in Chicago
5 out of 5 average rating, 5 reviewsArcade, Free Parking, TYLER The Creator Inspired
AnnaRating, 5 stars2 weeks ago
We had a group of 6 adults stay very comfortably here! The parking space was a great perk since we walked/ubered most places. Loved the space — decor was fun and the place was super clean. Kitchen and bathrooms well-stocked. Hosts are kind, responsive and accommodating! Definitely recommend
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- South Bend Holiday rentals
- Lake Michigan Beach Holiday rentals
- South Side Holiday rentals
- South Haven Holiday rentals
- Evanston Holiday rentals
- Saugatuck Holiday rentals
- Chicago Holiday rentals
- Hotel rentals Northwest Side
- Apartment rentals Northwest Side
- Rentals with a hot tub Northwest Side
- Rentals with breakfast Northwest Side
- Pet-friendly rentals Northwest Side
- Kid-friendly rentals Northwest Side
- Rentals with a fireplace Northwest Side
- Rentals with a patio Northwest Side
- Rentals with outdoor seating Northwest Side
- Condo rentals Northwest Side
- Fitness-friendly rentals Northwest Side
- Smoking-friendly rentals Northwest Side
- Private suite rentals Northwest Side
- Rentals with a washing machine and dryer Northwest Side
- House rentals Northwest Side
- Rentals with a fire pit Northwest Side
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Oak Street Beach
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- 875 North Michigan Avenue
- Six Flags Great America
- Wilmot Mountain Ski Resort
- The Field Museum
- Lincoln Park
- Wicker Park
- Lincoln Park Zoo
- Museum of Science and Industry
- Willis Tower
- Chicago History Museum
- Flossmoor Golf Club
- Brookfield Zoo
- Illinois Beach State Park
- Skokie Country Club
- Garfield Park Conservatory