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Chesapeake Bay Estate Homes for Rent

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St. Michaels Exceptional Waterfront Estate

  • 5 BR/6 BA, 2 half baths Estate (sleeps 10)
    $5,500/wk
    per property, pets considered, Hot Tub, Beach, Downtown, Resort, River, Rural, Town, Village, Waterfront, Private Pool, Jacuzzi, Lawn / Garden, terrace, Balcony

St. Michaels *****10% off stays of 3 nights or more for April and May******

  • 3 BR/2 BA, 1 half bath Estate (sleeps 9)
    $350 - $600/nt
    $2,400 - $3,750/wk
    $9,600 - $16,020/month
    per property, pets considered, Hot Tub, limited accessibility, Rural, Waterfront, Private Pool, Lawn / Garden, Fitness Room / Equipment, Air Conditioning

Oxford Historic Oxford Waterfront Estate welcoming 1-2 couples OR up to 12 guests

  • 6 BR/5 BA, 1 half bath Estate (sleeps 12)
    $350 - $750/nt
    $2,450 - $4,900/wk
    per property, Private Pool, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

St. Michaels Luxurious and Extremely Private Waterfront Estate

  • 8 BR/7 BA, 2 half baths Estate (sleeps 20)
    $1,200/nt
    $7,450 - $11,500/wk
    per property, pets considered, Rural, Waterfront, Private Pool, Tennis Court, Lawn / Garden, terrace, Balcony, Air Conditioning

St. Michaels Bay Cottage, St. Michaels, Md Waterfront Vacation Retreat: Pool, Dock,Farm, Bike

  • 6 BR/5 BA, 1 half bath Estate (sleeps 12)
    $759 - $1,419/nt
    $4,050 - $6,350/wk
    $12,150 - $19,050/month
    per property, Resort, Rural, Village, Private Pool, Lawn / Garden, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable, Television

St. Michaels Magnificent Vacation Rental home - 'Compass Rose' with pool and dock

  • 5 BR/2 BA, 1 half bath Estate (sleeps 8)
    $5,502/wk
    per property, wheelchair accessible, Downtown, River, Town, Waterfront, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

Easton Genteel, 30 Acre Waterfront Estate, Private, Close to Easton, Shops, and Dining

  • 6 BR/6 BA Estate (sleeps 12)
    $700 - $900/nt
    $5,000 - $6,000/wk
    per property, Private Pool, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

St. Michaels Luxury home with pool and deep water dock.

  • 4 BR/4 BA Estate (sleeps 8)
    $5,500/wk
    per property, Rural, Private Pool, Jacuzzi, Lawn / Garden, terrace, Balcony, Air Conditioning, Internet

St. Michaels Willows on the Miles - Private, waterfront farmhouse estate- Miles River

  • 5 BR/3 BA Estate (sleeps 12) pets considered, Waterfront, Private Pool, Satellite / Cable, Television, DVD Player, Fireplace

St. Michaels Waterfront vacation on a private, historic estate

  • 5 BR/3 BA, 1 half bath Estate (sleeps 12) accept credit card, pets considered, Waterfront, Private Pool, Air Conditioning, Internet, Satellite / Cable, Television

St. Michaels Longview -- Waterfront Estate w/ Pool & 3+ Acres

  • 5 BR/3 BA Estate (sleeps 10) Waterfront, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking, Fireplace

Oxford Eastern Shore Waterfront Estate, Private Beach, Deep Water

  • 8 BR/6 BA, 1 half bath Estate (sleeps 15) wheelchair accessible, Rural, Waterfront, Private Pool, Air Conditioning, Television, DVD Player, Parking, barbecue
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