Compare Vacation Rentals & Rent By Owner Homes in Chester Highlands, Chicago, Illinois, USA
About Chester Highlands Vacation Rentals
With more than 149 Chester Highlands 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 Chester Highlands.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Chester Highlands, 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 Chester Highlands. Places to stay near Chester Highlands are 730.03 ft² on average, with prices averaging US $304 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Chester Highlands with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Frequently Asked Questions About Chester Highlands?
What are the top vacation rentals in Chester Highlands?
- Home Away From Home
- Maison Blanc Noir - Victorian Estate with Two King Beds
- The Woodlawn Oasis is an absolutely beautiful newly rehabbed apartment!
- Charming house in amazing Chicago with WiFi and AC. Close to many restaurants.
- Newly remodeled 3 bedroom apt, a hidden gem 20 min to almost anyplace in Chicago
- Charming 3-bed, 3-bath house in amazing Chicago, 10 min from Midway Airport.
- Newly renovated modern retreat just blocks from I-94
- Gorgeous 5 Bedroom Gem Sleeps 18 with Pool, Ping Pong, Pac Man, Tons of Games!
- Charming 4-bedroom house with WiFi and AC in amazing Chicago
- Stylish 4BR South Loop Home State 23-202
How many Rentbyowner vacation rentals are available in Chester Highlands?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 149 in the Chester Highlands 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 Chester Highlands.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Chatham Vacation Rentals in Chicago, Illinois | 192 |
