We offer services for vacation rental owners who need assistance managing the details of their rental business. From websites, marketing, housekeeping, and emergency services - we can help you rent with confidence and peace of mind. As a property owner, or potential property owner, you’ve obviously fallen in love with the beach, just as we have. Seaside Vacations was founded with the belief that there was a better way to provide outstanding service, implement market leading technology, and provide the very best Eastern Shore Vacation experience possible all while providing value to both our Partners and Guests.

Trees listen to the Breeze; and then rustle its voice so beautifully…. Looking for a getaway that makes you feel a million miles from the real world? Just imagine kicking back under the shade of tall Pine Trees - swaying in the breeze, while you listen to the Tree Frogs sing - pure bliss. Whispering Pines is not just a place to lay your head at night - it’s a feeling - a true Vacation Experience. Nestled on a quiet cul-de-sac in a great mid-Island location, you’ll be close to everywhere you want to be, including Assateague National Seashore, where our famous Wild Ponies roam free. And, Whispering Pines welcomes your well-trained dog with no additional fee - 2 max! Must be pre-approved and current on flea/tick preventative. Now, it’s truly a Vacation for the whole family! As you pull down the long lane to this beautiful Duplex, you’ll know you made the right choice. Even though it’s a Duplex, it offers so much privacy and space. You’ll enter through the fabulous Screened Porch that lines the front of the house - kick off your Flip Flops and let the fun begin! You’ll love kicking back in the spacious Living Area with Free WiFi and Flat Screen Smart TV. There’s even a cozy Seasonal Fireplace for those chilly Off-Season Stays. Whispering Pines is the perfect getaway for any season, and we absolutely adore our Little Island by the Sea in the quieter months, as well! Sink into the comfy furnishings after a day of fun in the sun, and just BE together - what a wonderful concept! We love the Open Layout of Whispering Pines - it’s perfect for spending time together without ever feeling crowded. The Living Area opens to the Kitchen and Dining Area. Well-Stocked with all the comforts of home, mealtime will be anything but a chore. With both a Keurig and Mr. Coffee type pot, everyone will enjoy their favorite morning brew. Dine in the comfort of Central AC, or wander out to the Screened Porch and dine Al-Fresco under the shade of the Pine Trees. Grab a quick bite ...