Compare Vacation Rentals & Rent By Owner Homes in Chesapeake Bay, USA
About Chesapeake Bay Vacation Rentals
With more than 26544 Chesapeake Bay 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 Bay.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Chesapeake Bay, 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 Bay. Places to stay near Chesapeake Bay are 741.72 ft² on average, with prices averaging US $335 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Chesapeake Bay 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 Bay, US
Chesapeake Bay Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Chesapeake Bay?
- Stay in the HEART of Saint Michaels!
- Cottage on a Private Island in the York River
- Cozy, Dog-friendly Duplex At The North End Short Walk To The Beach!
- Adorable Cottage In The Heart Of The Old Beach Area, Close To The Boardwalk.
- The Holidays are over in Irvington. Just plop and do absolutely nothing!
- Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
- Captivating Chesapeake experience
- Historic Cottage on Ware River Estate
- Fantastic home in the heart of the VB Resort Area Walk to Beach, Boardwalk.
- Private Apt. in Historic Home: Walk to Monuments, Museums & Convention Center.
How many Rentbyowner vacation rentals are available in Chesapeake Bay?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 26544 in the Chesapeake Bay 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 Bay.
Nearby Neighborhood (16)
| Neighborhood | Property Count |
|---|---|
| Northwest Vacation Rentals in Chesapeake Bay, US | 2037 |
| Northeast Virginia Beach Vacation Rentals in Chesapeake Bay, US | 1159 |
| Northeast Vacation Rentals in Chesapeake Bay, US | 792 |
| Capitol Hill Vacation Rentals in Chesapeake Bay, US | 661 |
| Downtown Washington D.C. Vacation Rentals in Chesapeake Bay, US | 659 |
| Downtown Baltimore Vacation Rentals in Chesapeake Bay, US | 567 |
| Crystal City Vacation Rentals in Chesapeake Bay, US | 253 |
| Dupont Circle Vacation Rentals in Chesapeake Bay, US | 213 |
| Rosslyn Vacation Rentals in Chesapeake Bay, US | 194 |
| Downtown Vacation Rentals in Chesapeake Bay, US | 141 |
| Old Town Alexandria Vacation Rentals in Chesapeake Bay, US | 134 |
| Fells Point Vacation Rentals in Chesapeake Bay, US | 65 |
| Georgetown Vacation Rentals in Chesapeake Bay, US | 56 |
| Foggy Bottom Vacation Rentals in Chesapeake Bay, US | 49 |
| Pentagon City Vacation Rentals in Chesapeake Bay, US | 39 |
| Chic's Beach Vacation Rentals in Chesapeake Bay, US | 38 |
