There’s nothing like sipping on sweet tea as you sunbathe at your own private pool. Did you immediately imagine yourself enjoying this relaxing experience? Well, luckily for you, it doesn’t have to remain a daydream. Our collection of properties includes a wide variety of Eastern Shore, MD, vacation rentals with pools. Don’t worry about driving, trying to obtain a pass, or dealing with the crowds at public pools during your next vacation. In your Maryland vacation rental with a private pool, simply step outside and dip your toes into the cool, soothing waters of your own pool!
You’re only a few clicks away from finding your ideal vacation rental in the St. Michaels area. Put the pause on simply picturing this dreamy scene and start planning it! Scroll down and explore our Maryland vacation rentals with a private pool. You won’t regret it!

View Our Eastern Shore, MD, Vacation Rentals With Pools