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Search for vacation rental homes in Chesapeake Bay

  1. Chesapeake Bay Vacation Rental, quiet, beachy, open, bay view — Property 119031

    Vacation House rental in Chesapeake Bay area
    • House
    • 4 bedrooms , sleeps 12
    • 2 bathrooms
    • 1 half bathroom
    • beach, near the ocean
    • balcony
    $500 Fall Weekend Getaway special!!!
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1200 - $1500 per property per week
  2. Osprey's Nest
    Spacious,Peaceful,Comfort. Bay View,Eagles,Osprey,Sunrises from deck,Beaches — Property 248526

    Vacation House rental in Chesapeake Bay area
    • House
    • 4 bedrooms , sleeps 8
    • 3 bathrooms
    • beach, rural
    • balcony
    Fall Getaway Special 40% off peak rates
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $2000 - $2500 per property per week
  3. Budget friendly cottage getaway, with rowboat included! — Property 7022552

    Vacation Cottage rental in St. Michaels area
    • Cottage
    • 4 bedrooms , sleeps 8
    • 2 bathrooms
    • dock boatslip
    • DVD
    Rates (shown in USD)
    $1315 - $1940 per cottage per week
  4. Beautifully appointed vacation home outside St. Michaels — Property 7022556

    Vacation House rental in St. Michaels area
    • House
    • 6 bedrooms , sleeps 12
    • 5 bathrooms
    • dock boatslip
    • DVD
    Rates (shown in USD)
    $3251 - $5307 per house per week
  5. Chesapeake Bay Waterfront Luxury Vacation Home Near Solomon's Island — Property 122821

    Vacation House rental in St. Leonard area
    • House
    • 3 bedrooms , sleeps 10
    • 3 bathrooms
    • beach, waterfront
    • pets considered
    Rates (shown in USD)
    $1550 per property per week
  6. 90 acre farm with wrap around views, 5 minutes to St. Michaels, pool, dock — Property 7004794

    Vacation House rental in St. Michaels area
    • House
    • 4 bedrooms , sleeps 8
    • 2 bathrooms
    • dock boatslip
    • DVD
    Rates (shown in USD)
    $1453 - $3325 per house per week
  7. Conveniently located home between Easton and St. Michaels, private with Tred Avon views! — Property 7015502

    Vacation Cottage rental in St. Michaels area
    • Cottage
    • 3 bedrooms , sleeps 6
    • 2 bathrooms
    • dock boatslip
    • DVD
    Rates (shown in USD)
    $1375 - $2275 per cottage per week
  8. Tilghman Island getaway with private dock, great views, and more! — Property 7007436

    Vacation Cottage rental in Tilghman Island area
    • Cottage
    • 3 bedrooms , sleeps 6
    • 2 bathrooms
    • dock boatslip
    • DVD
    Rates (shown in USD)
    $1570 per cottage per week
  9. Charming Tilghman Island getaway cottage — Property 7007441

    Vacation Cottage rental in Tilghman Island area
    • Cottage
    • 4 bedrooms , sleeps 8
    • 2 bathrooms
    • DVD
    • fireplace
    Rates (shown in USD)
    $1060 - $1310 per cottage per week
  10. Fun house outside St. Michaels, pool, dock, hot tub, ping pong — Property 7007440

    Vacation House rental in St. Michaels area
    • House
    • 4 bedrooms , sleeps 8
    • 3 bathrooms
    • dock boatslip
    • DVD
    Rates (shown in USD)
    $1473 - $3345 per house per week

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