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.

A white two-story house with red shutters and a red metal roof, surrounded by a well-maintained lawn and trees.

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.

A house with a gravel driveway surrounded by trees and a well-maintained lawn.

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 | 7 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 bedroom one with four twin beds and the second with a queen bed.

Front view of a two-story brick house with a green front door, brown shutters, and small front yard with a sidewalk and some plants.

Rover’s Retreat

  • Step into history with this beautifully preserved 1907 home, perfectly located in the heart of Chestertown’s historic district. Just a block from Washington College and four blocks from Fountain Square, you’ll be surrounded by boutique shops, unique dining, and the vibrant Arts & Entertainment District along the Chester River. Experience the best of Maryland’s Eastern Shore right at your doorstep!

  • 6 Guests | 3 Bedrooms | 5 Beds | 2.5 Bath

    First floor - Double with en suite bath

    Second floor - 2 bedrooms: one with a queen bed, one with 3 twins, and there is a sitting room with a double futon; the house easily sleeps 7

A large brick house with a swimming pool in the backyard, surrounded by a white fence and lush greenery.

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!

  • 22 Guests | 11 Bedrooms | 11 Beds | 8.5 baths

    The main floor includes a siting room, family room, enclose sun room, dining room, gourmet kitchen, laundry room and one bedroom with a king bed.

    The second floor offers seven bedrooms with three queen beds and four king beds.

    The third floor offers two bedrooms, one king and one queen.

    An additional private entry bedroom with a private bath is available for an additional nightly fee.

Front view of a beige house with green shutters and a brown front door, surrounded by bushes and trees, with a partly cloudy sky overhead.

Hunter’s Retreat

  • 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.

Book a Stay