Chesapeake Bay Villa Rentals & Resorts

Find villas near Chesapeake Bay - We found 284 exact matches

About Chesapeake Bay Villa on Casai.ca

Casai boasts more than 284 an exceptional array of private villas near Chesapeake Bay. These opulent rentals epitomize luxury living, offering exclusive amenities such as private swimming pools, Wi-Fi, spas, hot tubs, and more.

Discover a diverse selection of villa rentals near Chesapeake Bay with Casai, catering to families, friends, and couples seeking indulgence and seclusion. Whether you desire a unique architectural style or a specific size, our collection of luxury villas ensures that every preference is met.

Embark on an unforgettable retreat with Casai's exclusive rental villas, each meticulously curated to offer an unparalleled experience. From secluded beachfront escapes to majestic mountainside havens, our all-in-one travel platform matches you with the perfect private villa in Chesapeake Bay for your dream vacation. Revel in lavish amenities such as private pools, sumptuous bedrooms, and additional features like tennis courts, beach volleyball, spas, fitness clubs, and beyond.

Experience the epitome of luxury with Casai's private villas, available for last-minute bookings and often accompanied by special offers for Airbnb, VRBO, and Casai-style villas. Explore your last-minute getaway today with Casai in Chesapeake Bay, and prepare to bask in the utmost comfort and sophistication on your next holiday.

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Frequently Asked Questions About Chesapeake Bay Rental Villas

There are a lot of options in Chesapeake Bay. If you plan on staying in the Chesapeake Bay area, consider making a reservation for a few nights at one of these properties as these have been rated the top Villa Rentals in Chesapeake Bay:

At Casai.ca, the average rental fee for standard villas in Chesapeake Bay is $420 per night. Casai has a large database of quality villas near Chesapeake Bay that are suitable for families, a romantic getaway, or a solo trip with single or multiple bedrooms.
Yes, here are the top villas rentals in Chesapeake Bay that are pet friendly:See all pet-friendly vacation rentals in Chesapeake Bay on Casai.ca
Most of our listed villas are suitable for families. The number of rooms varies, and you can check out the complete list of villas in Chesapeake Bay to find what works for you.
Based on the 2025 data from our Casai.ca site, there are more than 284 private swimming pools or villas with indoor pools in or near Chesapeake Bay.
There are 284 villas in or near Chesapeake Bay that have hot tubs. The most popular places to stay with hot tubs include:See all holiday vacation rentals in Chesapeake Bay on Casai.ca
Most definitely! There are many luxury villas in Chesapeake Bay. Use our search filter to discover all of our luxury villas, and choose the one that matches your taste. Sorting by price is another way to find the most expensive villas in Chesapeake Bay.