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 Northwest Side house rentals
House rentals with a pool
Home in Glen Ellyn
4.94 out of 5 average rating, 18 reviewsGlen Ellyn Home
Home in Plainfield
4.81 out of 5 average rating, 36 reviews30 mins to CHI*3 Kings*Fireplace*2 Desks*BBQ Grill
Home in Chicago
4.86 out of 5 average rating, 29 reviews2Bed+2Bath PentHouse in South Loop
Home in Bloomingdale
4.94 out of 5 average rating, 35 reviewsWhole House with a Hot Tub!
Home in Schaumburg
4.82 out of 5 average rating, 11 reviewsSchaumburg Oasis with a Pool and Hidden Garden
Home in Chicago
New place to stayCity Close, Country Calm
Home in Schaumburg
4.95 out of 5 average rating, 20 reviewsParadise 4BR w/ Pool & Games
Weekly house rentals
Home in Chicago
4.9 out of 5 average rating, 48 reviews3BD/2BA Chicago Avondale/Logan Square House
Home in Chicago
4.94 out of 5 average rating, 17 reviewsWrigley classic+trendy+2garage
Home in Chicago
5 out of 5 average rating, 65 reviewsNo Cleaning Fee Private Apt. Parking Near Airport
Home in Chicago
5 out of 5 average rating, 11 reviewsNEW! Large/Beautiful Home with 6BDS/4BTH + Garage!
Home in Skokie
4.88 out of 5 average rating, 84 reviewsLuxe-Haus of Love—The 1938 Cape Cod |Heated FLRS |
Home in Chicago
4.82 out of 5 average rating, 62 reviewsLogan Square Portrait Room
Home in Chicago
4.89 out of 5 average rating, 53 reviewsBrand New Spacious Duplex
Home in Chicago
4.93 out of 5 average rating, 86 reviewsHistoric 1920s bungalow near Logan Square !
Private house rentals
Home in Chicago
4.8 out of 5 average rating, 79 reviewsEntire 2 BR home w/ office, deck & no clean fee!
Home in Chicago
4.98 out of 5 average rating, 84 reviewsCasita Rosalinda - 3BR/2BA Chicago Home
Home in Skokie
4.88 out of 5 average rating, 90 reviewsA+amazing beauty, entire 2 BR Skokie historic stay
Home in Chicago
4.93 out of 5 average rating, 28 reviewsEntire Home in Historic Logan Square
Home in Skokie
4.96 out of 5 average rating, 46 reviewsCulinary DREAM - Pizza Oven/BBQ/Smoker
Home in Oak Park
4.97 out of 5 average rating, 79 reviewsModern Victorian Charm | A+ Location in OP
Home in Oak Park
5 out of 5 average rating, 33 reviewsOak Park - Wine House!
Home in Chicago
4.97 out of 5 average rating, 99 reviewsUltra Modern, 2800 SQ Ft, Outdoor Gazebo Sleeps 14
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- Saugatuck Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Bend Holiday rentals
- South Side Holiday rentals
- Schaumburg Holiday rentals
- Chicago Holiday rentals
- Lighthouse rentals United States
- Townhouse rentals United States
- Guesthouse rentals United States
- House rentals United States
- Earth house rentals United States
- Lakehouse rentals Chicago
- House rentals Chicago
- Townhouse rentals Chicago
- House rentals Downtown Chicago
- Townhouse rentals Downtown Chicago
- Lakehouse rentals Milwaukee
- House rentals Milwaukee
- Townhouse rentals Illinois
- Lakehouse rentals Illinois
- House rentals Illinois
- Guesthouse rentals Illinois
- Tiny house rentals Illinois
- Rentals with breakfast Northwest Side
- Pet-friendly rentals Northwest Side
- Rentals with outdoor seating Northwest Side
- Kid-friendly rentals Northwest Side
- Rentals with a hot tub Northwest Side
- Apartment rentals Northwest Side
- Rentals with a fireplace Northwest Side
- Rentals with a washing machine and dryer Northwest Side
- Condo rentals Northwest Side
- Fitness-friendly rentals Northwest Side
- Smoking-friendly rentals Northwest Side
- Private suite rentals Northwest Side
- Family-friendly rentals Northwest Side
- Rentals with a patio Northwest Side
- Rentals with a fire pit Northwest Side
- Monthly Rentals Northwest Side
- Hotel rentals Northwest Side
- Townhouse rentals Cook County
- Guesthouse rentals Cook County
- House rentals Cook County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
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- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
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- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom