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Search for vacation rental homes in Chesapeake Bay

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  1. Eastern Shore Paradise — Property 241115

    Vacation Condo rental in Chesapeake Bay area
    • Condo
    • 3 bedrooms , sleeps 8
    • 2 bathrooms
    • waterfront
    • pool
    Rates (shown in USD)
    $950 per property per week

  2. Dawnwood Organic Farm and Estate -w/20 Acres and a Pool, Free Vegetables. — Property 160678

    Vacation Farmhouse rental in Betterton area
    • Farmhouse
    • 5 bedrooms , sleeps 9
    • 2 bathrooms
    • 1 half bathroom
    • beach, rural
    • pool
    Rates (shown in USD)

  3. The Beach House - Fantastic, Fun, Family Vacation Home — Property 234151

    Vacation House rental in St. Michaels area
    • House
    • 4 bedrooms , sleeps 8
    • 1 bathroom
    • beach, waterfront
    • garden
    Rates (shown in USD)

  4. Matoaka Beach Cabins
    Rustic Beach Cabins on Chesapeake Bay — Property 233836

    Vacation Cabin rental in St. Leonard area
    • Cabin
    • 2 bedrooms , sleeps 6
    • beach, waterfront
    • parking
    Rates (shown in USD)

  5. St Michaels Premier Waterfront home with pool and dock — Property 138986

    Vacation House rental in St. Michaels area
    • House
    • 5 bedrooms , sleeps 10
    • 4 bathrooms
    • river
    • pool
    Rates (shown in USD)

  6. The Nourse Farm at St. Michaels — Property 124533

    Vacation House rental in St. Michaels area
    • House
    • 7 bedrooms , sleeps 20
    • 6 bathrooms
    • waterfront
    • air-conditioning
    Rates (shown in USD)

  7. St. Michaels Premier- Waterfront! — Property 113980

    Vacation Estate rental in St. Michaels area
    • Estate
    • 5 bedrooms , sleeps 11
    • 5 bathrooms
    • 1 half bathroom
    • garden
    • air-conditioning
    Rates (shown in USD)

  8. Longview - Waterfront Estate w/ Pool & 3+ Acres — Property 109333

    Vacation Estate rental in St. Michaels area
    • Estate
    • 5 bedrooms , sleeps 10
    • 3 bathrooms
    • waterfront
    • air-conditioning
    Rates (shown in USD)

  9. Tilghman Island Dreamin. A Beautiful Home Overlooking Dogwood Harbor — Property 151591

    Vacation Villa rental in Tilghman Island area
    • Villa
    • 4 bedrooms , sleeps 10
    • 2 bathrooms
    • 1 half bathroom
    • waterfront
    • jacuzzi
    Rates (shown in USD)

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