House holiday rentals in Chicago
Find and book unique houses on Airbnb
Top-rated house rentals in Chicago
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 Chicago house rentals
House rentals with a pool
Home in Highland Park
4.91 out of 5 average rating, 129 reviews2-Acre Highland Park Retreat with Heated Pool ~ 5*
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Schaumburg
4.86 out of 5 average rating, 7 reviewsParadise 4BR w/ Pool & Games
Home in Lincoln Park
4.87 out of 5 average rating, 39 reviewsLuxury Cabin in Lakeview
Home in Glen Ellyn
4.94 out of 5 average rating, 18 reviewsGlen Ellyn Home
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
Home in New Lenox
4.76 out of 5 average rating, 37 reviewsCheerful home. Heated pool, Hot tub!
Home in Plainfield
4.9 out of 5 average rating, 29 reviewsPool* 3 King beds* Grill & Patio* 30mi to Chicago
Weekly house rentals
Home in Whiting
4.8 out of 5 average rating, 231 reviewsWhiting Getaway
Home in West Loop
4.89 out of 5 average rating, 377 reviewsPro Cleaned & Isolated West Loop Coach House
Home in Des Plaines
4.78 out of 5 average rating, 315 reviewsUrban Farmhouse near O'Hare
Home in Chicago
4.9 out of 5 average rating, 94 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Home in Berwyn
4.99 out of 5 average rating, 85 reviewsRetro Modern Bungalow | fire pit | pet friendly
Home in Jefferson Park
4.86 out of 5 average rating, 74 reviewsChicago getaway for two!
Home in Lake View
4.98 out of 5 average rating, 63 reviews2BD/1 BA with summer patio in quiet Roscoe Village
Home in Lake View
4.97 out of 5 average rating, 31 reviewsLakeview Condo
Private house rentals
Home in Garfield Ridge
5 out of 5 average rating, 21 reviewsChicago Home by Midway near Downtown Attractions
Home in Wrigleyville
4.99 out of 5 average rating, 77 reviewsWhole apartment! 2 Bed/2 bath steps from Wrigley!!
Home in Bridgeport
5 out of 5 average rating, 56 reviewsCozy, Quiet, Riverwalk Sanctuary
Home in Lincoln Park
5 out of 5 average rating, 57 reviewsCharming 3-BED in Lincoln Park/ Old Town & Parking
Home in Highland Park
4.97 out of 5 average rating, 69 reviewsCharming Ranch-Style Cottage
Home in Logan Square
4.97 out of 5 average rating, 35 reviewsLight and bright 3BD duplex in Avondale, Chicago
Home in Munster
4.95 out of 5 average rating, 42 reviewsEntire home: Private, Cozy Oasis in Quiet Locale
Home in Lombard
5 out of 5 average rating, 69 reviewsModern Boho house in Lombard 7 min to Metra
Quick stats about house rentals in Chicago
Total rentals
1.8K properties
Rentals with dedicated workspaces
1.2K properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
470 properties allow pets
Family-friendly rentals
950 properties are a good fit for families
Total number of reviews
69K reviews
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- Schaumburg Holiday rentals
- Townhouse rentals United States
- Earth house rentals United States
- House rentals United States
- Guesthouse rentals United States
- Lighthouse rentals United States
- Rentals with an accessible height bed Chicago
- Rentals with breakfast Chicago
- Rentals with a fire pit Chicago
- Rentals with a home theatre Chicago
- Rentals with outdoor seating Chicago
- Kid-friendly rentals Chicago
- Bed and breakfasts Chicago
- Smoking-friendly rentals Chicago
- Rentals with a patio Chicago
- Private suite rentals Chicago
- Beachfront rentals Chicago
- Apartment rentals Chicago
- Townhouse rentals Chicago
- Loft rentals Chicago
- Family-friendly rentals Chicago
- Rentals with a balcony Chicago
- Rentals with a sauna Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- Monthly Rentals Chicago
- Rentals with lake access Chicago
- Rentals with an EV charger Chicago
- Lakehouse rentals Chicago
- Rentals with a washing machine and dryer Chicago
- Fitness-friendly rentals Chicago
- Mansion rentals Chicago
- Boutique hotel rentals Chicago
- Rentals with beach access Chicago
- Condo rentals Chicago
- Rentals with a hot tub Chicago
- Waterfront rentals Chicago
- Rentals with pools Chicago
- Rentals with a fireplace Chicago
- House rentals Downtown Chicago
- Townhouse rentals Downtown Chicago
- House rentals Milwaukee
- Lakehouse rentals Milwaukee
- House rentals Lake Geneva
- Lakehouse rentals Lake Geneva
- Tree house rentals Illinois
- Townhouse rentals Illinois
- Lakehouse rentals Illinois
- House rentals Illinois
- Tiny house rentals Illinois
- Guesthouse rentals Illinois
- 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
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom