Compare Vacation Rentals & Rent By Owner Homes in Old Town, Chicago, Illinois, USA
About Old Town Vacation Rentals
With more than 88 Old Town vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Old Town.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Old Town, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Old Town. Places to stay near Old Town are 1111.46 ft² on average, with prices averaging R8,890 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Old Town with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Other Places to Stay in Old Town, IL
Frequently Asked Questions About Old Town?
What are the top vacation rentals in Old Town?
- The Sono Chicago
- Large 4BR/3BA Safe Old Town Location Walk Everywhere
- Luxury House in the heart of Old Town with Parking
- Lovely 4 Bedroom Spot located in Charming Old Town
- THE COMPOUND Large Exquisite House Private Yard 'Best Location' Well Appointed
- GROUP LUX in Old Town/Gold Coast (+private roof)
- Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly
- Chicago’s BEST location… Lincoln Park, Lake Michigan, Wrigley Field, and more!
- MTM Fully Furnished Rental in Old Town - 2 beds
- A home away from home!
How many Rentbyowner vacation rentals are available in Old Town?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 88 in the Old Town area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Old Town.
Nearby Neighborhood (10)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Vacation Rentals in Chicago, Illinois | 1233 |
| Near North Side Vacation Rentals in Chicago, Illinois | 494 |
| River North Vacation Rentals in Chicago, Illinois | 280 |
| Lincoln Park Vacation Rentals in Chicago, Illinois | 120 |
| Rush and Division Vacation Rentals in Chicago, Illinois | 58 |
| Old Town Triangle Vacation Rentals in Chicago, Illinois | 46 |
| Gold Coast Vacation Rentals in Chicago, Illinois | 31 |
| Mid-North District Vacation Rentals in Chicago, Illinois | 3997 |
| Sheffield Neighbors Vacation Rentals in Chicago, Illinois | 4082 |
| Ranch Triangle Vacation Rentals in Chicago, Illinois | 4447 |
