The Properties

Shore Stay Rentals presents exclusive properties for short-term rentals on the upper Eastern Shore. Your perfect getaway awaits – come, stay a while.

Cliff Pines

  • Relax on the scenic Eastern Shore. Located just off the Chester River. Step away from the hustle and bustle to our cozy cottage appointed with modern amenities.

    The tranquil backyard offers a fire pit and picnic table for entertaining.

  • 6 Guests | 2 Bedrooms | 2 Beds | 1 Bath

    The main floor includes a spacious living room, dining room and kitchen.

    The second floor offers two spacious bedrooms with a loft that includes the bunk beds.

    Outside has a spacious deck with a picnic table and grill that overlooks a patio with a fire pit for guests to enjoy in the evenings.

    Additional entertainment amenities include (2) kayaks, (2) bikes, horse shoes, and fishing poles.

Sassafras Lodge

  • The Sassafras Lodge welcomes groups to a quaint country setting in the Sassafras River watershed.

    The lodge is situated overlooking beautiful farmland to help guests escape life's daily hustle and bustle while still having all of the amenities to be connected to the "real world."

  • 8 Guests | 4 Bedrooms | 6 Beds | 2 Baths

    The main floor includes a spacious living room, dining room, and kitchen. Two bedrooms, one king and one queen.

    The second floor offers two bedrooms with two twins in each.

The Anchorage

  • The Anchorage is the perfect property for groups, big or small, to escape the hustle and bustle and enjoy our serene setting with breathtaking views of endless farmland. Nestled between Georgetown, MD, Chesapeake City, MD & Middletown, DE there is plenty to offer in terms of food, entertainment and activities!

  • 16+ Guests | 10 Bedrooms | 10 Beds | 8.5 baths

    The main floor includes a spacious living room, dining room and kitchen.

    The second floor offers two spacious bedrooms with a loft that includes the bunk beds.

    Outside has a spacious deck with a picnic table and grill that overlooks a patio with a fire pit for guests to enjoy in the evenings.

    Additional entertainment amenities include (2) kayaks, (2) bikes, horse shoes, and fishing poles.