
House holiday rentals in Old Town
Find and book unique houses on Airbnb
Top-rated house rentals in Old Town
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 Old Town house rentals
House rentals with a pool

Comfortable 3BR Home-Prime Video, WiFi, Parking

Pool & Beach Haven-private pool, steps to beach!

Munster hide away

Now Open: Heated Pool with Entire House

Highwood Haven/Indoor Pool/Hot Tub/Arcade

Downtown 2BR: Unique Amenities, Ideal for Tourism

Schaumburg Oasis:Private Pool & Enchanted Garden

Luxury Loft with Private Pool and Movie Theater
Weekly house rentals

Gold Coast Home|Rooftop |PoolTable |Parking |Views

Old Town Retreat

Duplex Home RoscoeVillage/Wrigley Free St Parking

The Roscoe House near Wrigley Field

Spacious Five Bedroom Home in Trendy Chicago Neighborhood

Larimer Park Carriage House

Opulent 3bdr2bth Old Town Luxury + Parking prmts

Vintage Walk-up in Old Town
Private house rentals

The Boxcar

NEW! 3BR/2.5B Duplex in Noble Sq

Casa 22 | Luxury Modern House for 6 | 3 Bed,2 Bath

jane's house - a boutique flat in west town -2b/1b

Cheryl's on Sheffield! 3 bedroom in Lincoln Park.

WrigleyRoost <5 min to Cubs/train/lake!

Lakeview Condo

Wrigleyville Single Family
Quick stats about house rentals in Old Town
Total rentals
20 properties
Nightly prices starting at
$204 NZD before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Destinations to explore
- Family-friendly rentals Old Town
- Rentals with a fireplace Old Town
- Rentals with a washing machine and dryer Old Town
- Pet-friendly rentals Old Town
- Apartment rentals Old Town
- Rentals with a patio Old Town
- Rentals with outdoor seating Old Town
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Illinois Beach State Park
- Wicker Park
- Garfield Park Conservatory
- Washington Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Lincoln Park Zoo
- Willis Tower
- Raging Waves Waterpark
- The 606
- The Beverly Country Club