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Latest Vacation Rentals in Shady Side MD (12)

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4 Br Private Vacation Home Vacation Rental In Shady Side, Maryland

Expansive views of the Cheasapeake Bay, located on the West River this home is private, peaceful and immaculate. Home includes private dock with boat lift, 1 car garage and a large open floor plan....

Created Apr 14, 2024

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3 Br Private Vacation Home Vacation Rental In Shady Side, Maryland

Gorgeous view, expansive covered back porch with fans & cascading stairs down to paver patio, fire pit and a dock where you catch an abundance of crabs! Large master suite with huge bath offering...

Created Apr 14, 2024

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6 Br Private Vacation Home Vacation Rental In Shady Side, Maryland

Welcome to our waterfront oasis on Parishs Creek just off of the Chesapeake Bay! Our spacious house is the perfect retreat for fishing enthusiasts, nature lovers, and those seeking a serene...

Created Apr 14, 2024

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3 Br Private Vacation Home Vacation Rental In Shady Side, Maryland

A beautifully furnished quiet oasis to kick back and relax or if you are fast paced, you can visit many of the attractions and bars in the areaMarina located right across the street for anyone who...

Created Apr 14, 2024

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3 Br Cabin Vacation Rental In Shady Side, Maryland

Relax with the whole family at this peaceful Cabin off the Chesapeake.This 3bd 1 bath can accommodate 9-12 people.Enjoy the sunshine with some peace of mind relaxing on the screen in porch away...

Created Apr 14, 2024

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3 Br Private Vacation Home Vacation Rental In Shady Side, Maryland

Tucked between the Chesapeake Bay and 500 acres of state park, this round house sits on a peninsula with panoramic views to indulge the senses. Listen to and photograph eagles, ospreys, and...

Created Apr 14, 2024

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2 Br Cottage Vacation Rental In Shady Side, Maryland

About this spaceEscape to our peaceful, riverside cottage. Enjoy sweeping views of the West River with 390 feet of private waterfront. Spectacular sunsets, blue heron and birds galore. Cottage is...

Created Apr 14, 2024

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3 Br Private Vacation Home Vacation Rental In Shady Side, Maryland

A quiet, seaside escape awaits at this Shady Side vacation rental, hosting 3 bedrooms, 2 baths, at-home comforts and access to the neighborhoods amenities - including a boat launch, pier, and more!...

Created Apr 14, 2024

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3 Br Private Vacation Home Vacation Rental In Shady Side, Maryland

Calloway Drive RetreatOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Steps from the bay, curate all of your...

Created Apr 14, 2024

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6 Br Private Vacation Home Vacation Rental In Shady Side, Maryland

Pier Relaxation with the whole family at this peaceful place to stay on the Chesapeake Bay! Fishing or crabbing from the community pier. Less than an hour to DC or 30 minutes to Annapolis. Pet...

Created Apr 14, 2024

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3 Br Private Vacation Home Vacation Rental In Shady Side, Maryland

Updated 3 bedroom, 2 bathroom private cottage is situated in a water community on the beautiful Chesapeake Bay. Take advantage of all the Chesapeake Bay has to offer during your stay. We have...

Created Apr 14, 2024

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4 Br Private Vacation Home Vacation Rental In Shady Side, Maryland

5-years-young STUNNING home with OPEN concept, soaring ceilings, hardwoods, gas fireplace, separate laundry room, backyard patio & gorgeous finishes! Enjoy all that the Chesapeake Bay area has to...

Created Apr 7, 2024

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