Ocean Pines Escape

A quaint, newly renovated beach house in Ocean Pines, with three bedrooms and two baths. Full size kitchen with dining table for 6. It has a screened in deck out back with a grill. Use of parking pass for the Ocean Pines Beach Club in Ocean City, with acess to bar and concessions. Enough parking for 4-5 vehicles. Basketball hoop in driveway which is big enough for pickle ball. Games and PacMan video arcade for indoor fun. Non- smoking on property. No high school senior week guests.

19th Century Coastal Cottage with Modern Amenities

Built from “clinker bricks” in 1941 to house poultry feed, this Airbnb is a dreamy place to slow down. Exposed wood beams and interior brick walls as well as all the luxuries required for a rural escape. This charming cottage near the beach & is surrounded by enchanted gardens. You will swoon over the carved marble bathtub and gorgeous living areas. Perfect for a romantic getaway, Hobbs and Rose Cottage is waiting to create a memorable experience for you! NEW for 2025, our mediation room!

Newly built bright and airy guest suite!!!!

Welcome to our new 2nd floor private suite with parking, patio/firepit, and self check-in private entry. We are located just minutes from the Ocean City beaches, quaint small town of Berlin, Ocean Downs Casino, Assateague, Windmill Creek Winery, restaurants, and outlets. Enjoy neighborhood amenities such as a breathtaking waterfront Yacht Club with restaurant and live music (seasonal), Robert Trent Jones Sr. golf, farm market, playgrounds, 5 pools/fee (4 seasonal), and racquet club.

Serene OP cottage perfect for your next getaway!

Welcome to our Peaceful Pines Retreat located in the amenity rich community of Ocean Pines! Whether you are looking for a little R&R or seeking some outdoor adventure, you can enjoy it all just minutes from our cozy, inviting and updated coastal cottage. Our home is located just 8 miles from Ocean City, 7 miles from Berlin (voted America’s Coolest Small Town) 13 miles to Assateague State Park and 2.6 miles to Ocean Downs Casino among many other attractions. Rental Lic # 4033

Ocean Pines Hideaway

This 3-bed, 2-bath home in Ocean Pines sleeps 8 and is ideal for a beach getaway. The spacious interior includes a fully-equipped kitchen, a cozy living area, and a master suite with an en-suite bath. Outdoors, enjoy a large yard with a grill and seating for relaxing or dining. Just a short drive to Ocean City’s beaches, boardwalk, outlet shops, amusement parks, and restaurants, this home offers the perfect blend of comfort and convenience for your next vacation.

Ocean Pines MD Shady Rest Getaway

We Welcome you to Shady Rest Ocean Pines! My name is HC and I will be hosting you here at Shady Rest Ocean Pines along with my son Elijah. This property was our first family home and turning it into an Airbnb has allowed us to keep it in the family while sharing the tranquility that Ocean Pines has to offer to others. We hope you can create some memories here as we have as a family. Please enjoy your little Shady Rest Gateway! -From The Whaleys'