Our vacation rentals are strategically located to offer breathtaking views and proximity to local attractions. Whether you prefer a secluded woodland setting or a waterfront oasis, Chesapeake Stays provides the ideal backdrop for your vacation.

From private pools and hot tubs to gourmet kitchens and spacious living areas, our rentals are equipped with everything you need for a luxurious and comfortable experience.

Whether you require grocery delivery, in-house chefs, or recommendations for local activities, our dedicated team is here to ensure your stay is seamless and stress-free.

Our vacation rental properties offer a safe and secure environment where you can unwind and enjoy quality time with loved ones.

Chesapeake Stays prides itself on spacious interiors and elegant furnishings. Our rentals feature multiple bedrooms, expansive living areas, and high-quality amenities that guarantee a comfortable and luxurious stay.

Each of our properties boasts unique architectural designs that blend modern luxury with local charm. From contemporary beachfront villas to historic estates, our rentals offer a one-of-a-kind experience that reflects the beauty of the Chesapeake Bay region.

Cook up a storm in our gourmet kitchens equipped with state-of-the-art appliances. Alternatively, indulge in the services of a private chef who can prepare custom menus tailored to your preferences, ensuring a memorable dining experience.

Chesapeake Stays is perfect for families with children, offering amenities such as game rooms, outdoor play areas, and kid-friendly accommodations. We provide everything you need to ensure your little ones are comfortable and entertained throughout your stay.

Stay connected with high-speed internet, smart TVs, and entertainment systems available in all of our rentals. Enjoy the convenience of modern technology while experiencing the beauty of nature.