Compare Vacation Rentals & Rent By Owner Homes in Chesapeake, Virginia, USA
About Chesapeake Vacation Rentals
With more than 179 Chesapeake 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 Chesapeake.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Chesapeake, 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 Chesapeake. Places to stay near Chesapeake are 465.29 ft² on average, with prices averaging US $223 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Chesapeake 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 Chesapeake, VA
Frequently Asked Questions About Chesapeake?
What are the top vacation rentals in Chesapeake?
- Fully renovated and Modernized home in Chesapeake
- Beautiful home in Chesapeake
- Looking for 30 days or more contact me via VRBO for special pricing. Hot Tub
- The Sparks Home! Relaxing Space + Lux Kitchen
- The Full House
- NEWLY REMODELED 2 BEDROOM DUPLEX
- Perfect Getaway in Chesapeake
- Fenced Yard & Patio! 2,400-Sq-Ft Chesapeake Home
- King Guest Suite - A TOGAR Vacation Rental
- Oasis at the Creek
How many Rentbyowner vacation rentals are available in Chesapeake?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 179 in the Chesapeake 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 Chesapeake.
Nearby Neighborhood (7)
| Neighborhood | Property Count |
|---|---|
| Greenbrier East Vacation Rentals in Chesapeake, Virginia | 185 |
| Western Branch North Vacation Rentals in Chesapeake, Virginia | 71 |
| Greenbrier West Vacation Rentals in Chesapeake, Virginia | 66 |
| Deep Creek South Vacation Rentals in Chesapeake, Virginia | 149 |
| Great Bridge Vacation Rentals in Chesapeake, Virginia | 106 |
| Churchland Vacation Rentals in Chesapeake, Virginia | 66 |
| Great Bridge East Vacation Rentals in Chesapeake, Virginia | 27 |
