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Your next vacation destination

Eastern Shore of Maryland

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The moment you arrive on the Eastern Shore, you're wrapped in a tangible warmth that immediately embraces you, extending a genuine welcome that goes beyond mere hospitality. It's a haven of kindness. From the first glance, you'll know – this is more than just a stay, it’s an invitation to immerse yourself in the authentic charm of what we call Chesapeake Country.

The Properties

A white two-story house with red shutters and a red roof, surrounded by green grass and trees, with a black door in the center and a flower bed in front.

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 white house with a brown roof and a chimney, surrounded by green trees and a gravel driveway in a spacious yard.

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.

A two-story beige brick house with orange window shutters and a green front door decorated with a holiday wreath. Small bushes flank the doorway, and there are cars parked on the street and driveway. The yard has patches of grass and dirt, with a small garden on the left and a drain pipe sticking out from the ground.

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 and beige residential building with multiple chimneys, a swimming pool, and a surrounding white fence in a green landscape with trees and a blue sky.

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.

A two-story house with beige siding, green shutters, and a wooden front door, surrounded by shrubbery and trees, with a lawn in the foreground and a partly cloudy sky above.

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.

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