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Chesapeake Bay Home Rentals by Owner

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Port Republic Spacious beachfront getaway overlooking Chesapeake Bay

  • 3 BR/2 BA House (sleeps 10)
    $300/nt
    $1,750/wk
    per property, pets considered, Beach, Waterfront, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

North Beach Waterfront, Water All Around, Peaceful Family Getaway

  • 3 BR/1 BA House (sleeps 6)
    $229 - $350/nt
    $1,400 - $1,600/wk
    per property, Beach, Waterfront, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

St. Leonard Chesapeake Bay retreat on Flag Harbor Marina. Fantastic!

  • 4 BR/2 BA House (sleeps 10)
    $250 - $300/nt
    $1,470/wk
    per property, accept credit card, pets considered, Beach, Waterfront, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Cambridge Welcome Home to Sunset Bay

  • 5 BR/3 BA, 1 half bath House (sleeps 13)
    $750/nt
    $4,900 - $5,250/wk
    $21,000 - $21,000/month
    per property, Waterfront, Private Pool, Balcony, Air Conditioning, Satellite / Cable, Television, DVD Player, Parking

Solomons Island Cedar Beach Lodge is a Modern Year-Round Retreat on the Chesapeake Bay

  • 3 BR/2 BA House (sleeps 8)
    $300 - $350/nt
    $1,750 - $1,925/wk
    $3,750/month
    per property, accept credit card, pets considered, Beach, Rural, Waterfront, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television

North Beach Breath-taking waterfront house on Chesapeake Bay-North Beach, MD!

  • 2 BR/2 BA, 1 half bath House (sleeps 6)
    $349/nt
    $1,995/wk
    $4,296/month
    per property, accept credit card, Beach, Waterfront, Jacuzzi, Lawn / Garden, terrace, Air Conditioning, Internet, Television

Deale Million Dollar View on the Chesapeake Bay

  • 4 BR/3 BA House (sleeps 10)
    $250 - $300/nt
    $1,650 - $1,925/wk
    per property, Waterfront, Jacuzzi, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Port Republic Stone's Throw - Bayfront Log Cabin with 180 degree View in Exclusive Community

  • 2 BR/1 BA House (sleeps 5)
    $150 - $260/nt
    $1,150 - $1,750/wk
    per property, accept credit card, Beach, Resort, Rural, Waterfront, Communal Pool, Tennis Court, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable

Cobb Island Enjoy the Water? Fishing, Crabbing, Boating? Here it is!

  • 4 BR/2 BA, 1 half bath House (sleeps 9)
    $2,030/wk
    $6,750/month
    per property, accept credit card, pets considered, River, Rural, Waterfront, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

Deal Island Lovely Custom Built Chesapeake Bay Cottage with beautiful water views!

  • 3 BR/2 BA House (sleeps 8)
    $95 - $150/nt
    $600 - $895/wk
    per property, accept credit card, pets considered, Rural, Village, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

St. Leonard Osprey's Nest, Spacious, Peaceful, Bay Views, Sunrises, Relaxing

  • 4 BR/3 BA House (sleeps 10)
    $357 - $400/nt
    $2,000 - $2,500/wk
    per property, accept credit card, pets considered, wheelchair accessible, Beach, Rural, Balcony, Air Conditioning, Internet, Satellite / Cable

Port Republic Magical Bayfront Home

  • 3 BR/2 BA House (sleeps 8)
    $350 - $425/nt
    $2,000 - $2,800/wk
    per property, accept credit card, pets considered, limited accessibility, wheelchair accessible, Beach, Waterfront, Air Conditioning, Internet, Satellite / Cable

North East Life On The Water

  • 3 BR/3 BA House (sleeps 8)
    $375/nt
    $2,100/wk
    per property, limited accessibility, River, Waterfront, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Kent Island Peaceful, Waterfront Cottage w/Pier (close to St. Michaels & Annapolis)

  • 4 BR/2 BA House (sleeps 8)
    $280 - $375/nt
    $1,960/wk
    per property, limited accessibility, Rural, Waterfront, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

St. Michaels ***15% off 3 nights or more in MAY*** Holiday weekends excluded

  • 3 BR/3 BA, 1 half bath House (sleeps 8)
    $275 - $450/nt
    $1,600 - $3,000/wk
    $6,000/month
    per property, accept credit card, River, Rural, Village, Waterfront, Communal Pool, Jacuzzi, Lawn / Garden, Balcony, Air Conditioning, Internet

St. Leonard Chesa. Bay Vacation Rental, quiet, beachy, open, bay view, LAST MIN. SPECIALS!

  • 4 BR/2 BA, 1 half bath House (sleeps 12)
    $350 - $400/nt
    $1,700 - $2,000/wk
    per property, accept credit card, pets considered, Beach, Near The Ocean, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

St. Michaels 'Sandy Pines' 4 BR on Harris Creek w/Pool, Dock, Paddle boards, Kayaks, Sunfish

  • 4 BR/3 BA House (sleeps 10)
    $375 - $657/nt
    $2,600 - $4,600/wk
    per property, River, Waterfront, Private Pool, Lawn / Garden, terrace, Air Conditioning, Internet, Satellite / Cable, Television

St. Michaels Historic Waterfront Home in St. Michaels, w/Wi-Fi, Dock & Pet Friendly

  • 4 BR/2 BA, 1 half bath House (sleeps 8)
    $500 - $750/nt
    $2,000 - $3,300/wk
    per property, accept credit card, pets considered, River, Waterfront, Communal Pool, Lawn / Garden, Balcony, Air Conditioning, Internet

North Beach Relaxing House on Chesapeake Bay

  • 3 BR/2 BA, 1 half bath House (sleeps 8)
    $1,351/wk
    per property, Waterfront, Balcony, Air Conditioning, Satellite / Cable, Television, DVD Player, barbecue, Fireplace

Point Lookout Chesapeake Charm - Fishing, Crabbing, Boating & Chillin'

  • 3 BR/2 BA, 1 half bath House (sleeps 9)
    $200 - $300/nt
    $1,400 - $1,750/wk
    per property, pets considered, Rural, Lawn / Garden, Air Conditioning, Satellite / Cable, Television, DVD Player, Parking

North East Lovely waterfront home with pier. Wonderful quiet getaway!

  • 2 BR/2 BA House (sleeps 6)
    $200 - $236/nt
    $1,575 - $1,650/wk
    per property, pets considered, River, Waterfront, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

St. Michaels MisBayhaven...Luxury Large Waterfront Home, Sunsets, Pool, 2 miles from town

  • 5 BR/4 BA House (sleeps 10)
    $525 - $957/nt
    $6,700/wk
    per property, Hot Tub, Town, Waterfront, Private Pool, Lawn / Garden, terrace, Air Conditioning, Internet, Satellite / Cable

Tilghman Island Summer Fun at a Huge Waterfront Home - Perfect for Families or Groups

  • 6 BR/5 BA, 1 half bath House (sleeps 15)
    $786 - $1,000/nt
    $5,250 - $5,500/wk
    $18,000/month
    per property, pets considered, Private Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, Parking

North East Top of the Chesapeake - Minutes from Historic Charlestown

  • 5 BR/2 BA House (sleeps 15)
    $359 - $429/nt
    $2,499 - $2,699/wk
    per property, accept credit card, pets considered, limited accessibility, River, Waterfront, Balcony, Air Conditioning, Internet, Satellite / Cable

Port Republic Private Beachfront Home with Beautiful Bay View

  • 4 BR/2 BA House (sleeps 12)
    $1,900 - $2,900/wk
    per property, accept credit card, Beach, Waterfront, Communal Pool, Tennis Court, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable

St. Michaels Magnificent 6500 sq ft estate vacation home 'The Tred Avon Manor'

  • 7 BR/5 BA House (sleeps 12)
    $1,143 - $1,200/nt
    $7,000 - $8,000/wk
    per property, pets considered, River, Rural, Waterfront, Private Pool, Lawn / Garden, terrace, Balcony, Air Conditioning, Internet

St. Michaels Europa on the Beach - Architectural contemporary home on the Chesapeake Bay

  • 3 BR/2 BA House (sleeps 6)
    $643 - $650/nt
    $4,500/wk
    per property, Hot Tub, Waterfront, Private Pool, Lawn / Garden, terrace, Balcony, Air Conditioning, Internet

Elkton Stunning 7-Acre Chesapeake Bay Estate

  • 7 BR/5 BA, 1 half bath House (sleeps 18)
    $745 - $1,095/nt
    $6,585 - $7,665/wk
    $18,750/month
    per property, pets considered, Hot Tub, Private Pool, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television

North Beach Herrington Harbour - Beautiful Single Family Home - Rose Haven

  • 3 BR/2 BA House (sleeps 7)
    $300/nt
    $1,400/wk
    per property, accept credit card, Resort, Waterfront, Private Pool, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

St. Michaels Sunrises AND Sunsets, Panoramic Views with Pool and Deepwater Dock, Sleeps 10

  • 4 BR/5 BA House (sleeps 10)
    $600 - $850/nt
    $4,200 - $5,700/wk
    per property, accept credit card, pets considered, River, Rural, Village, Waterfront, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet

Chestertown Fantastic 360 Farm With Grand 5 Bedroom Manor Home

  • 5 BR/2 BA, 1 half bath House (sleeps 10)
    $929 - $1,000/nt
    $6,500/wk
    $20,000/month
    per property, Rural

Cobb Island Cobb Island / Potomac Waterfront - Private Beach & Dock- Fish, Swim, Crab, Kayak

  • 4 BR/2 BA House (sleeps 9)
    $200 - $565/nt
    $1,800 - $2,500/wk
    per property, accept credit card, River, Waterfront, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

Cambridge Renovated Historic Waterfront Home with Pool, Dock, 200 acres

  • 7 BR/3 BA, 1 half bath House (sleeps 18)
    $600 - $686/nt
    $3,800 - $4,800/wk
    per property, pets considered, wheelchair accessible, River, Rural, Waterfront, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television

St. Michaels Summer 2014 Specials! Vineyard at Thornton - magnificent

  • 5 BR/3 BA, 1 half bath House (sleeps 10)
    $900/nt
    $5,600/wk
    $16,800/month
    per property, pets considered, Rural, Waterfront, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

St. Michaels Incredible Waterfront Home 'Wye Provence' ' With Pool And Dock

  • 5 BR/3 BA, 1 half bath House (sleeps 10)
    $850/nt
    $5,250/wk
    per property, pets considered, River, Rural, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Satellite / Cable, Television

St. Michaels St Michaels Extraordinary Waterfront home on 54 acres with pool, dock, beach...

  • 5 BR/5 BA, 1 half bath House (sleeps 10)
    $1,500/nt
    $8,000/wk
    per property, pets considered, River, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

St. Michaels Brand new waterfront estate....luxury and privacy on ten acres!

  • 4 BR/3 BA, 1 half bath House (sleeps 9)
    $475 - $725/nt
    $2,995 - $4,200/wk
    $5,500/month
    per property, accept credit card, pets considered, Rural, Waterfront, Private Pool, Jacuzzi, Balcony, Air Conditioning, Satellite / Cable

Tilghman Island Charming 2 story dutch colonial on the Chesapeake Bay

  • 3 BR/2 BA House (sleeps 6)
    $350/nt
    $1,800 - $2,000/wk
    per property, pets considered, Downtown, Village, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

Tilghman Island Charming and elegant with a water view of Knapps Narrows

  • 3 BR/2 BA House (sleeps 6)
    $275 - $300/nt
    $1,932/wk
    per property, Village, Waterfront, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Cambridge Fishing Cove Private Waterfront Retreat with Pool and Pier

  • 8 BR/6 BA House (sleeps 22)
    $430 - $800/nt
    $2,200 - $5,200/wk
    per property, accept credit card, pets considered, wheelchair accessible, Waterfront, Private Pool, Jacuzzi, Balcony, Air Conditioning

North East Unique Lighthouse home & tenant houses with waterfront, dock, ramp, beach

  • 4 BR/4 BA House (sleeps 8)
    $575/nt
    $3,100/wk
    per property, accept credit card, Hot Tub, wheelchair accessible, Beach, Waterfront, Jacuzzi, Balcony, Air Conditioning, Satellite / Cable

North East Waterfront home with dock, ramp, beach overlooking sandy beach

  • 4 BR/3 BA House (sleeps 8)
    $465/nt
    $2,500/wk
    per property, Lawn / Garden, Balcony, Air Conditioning, Satellite / Cable, Television, Parking, Fireplace

North East Affordable, unique, completely remodeled waterfront home. dock, ramp, beach

  • 4 BR/1 BA House (sleeps 8)
    $335/nt
    $1,800/wk
    per property, Air Conditioning, Satellite / Cable, Television, Parking, Fireplace

Port Republic Treasure the Chesapeake Bay w/Beachfront Home

  • 3 BR/2 BA House (sleeps 6)
    $300 - $307/nt
    $1,600 - $2,150/wk
    per property, Beach, Waterfront, Communal Pool, Tennis Court, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

St. Michaels Reserve Now for Waterfowl Festival! Luxury Waterfront, 13 Acre Estate

  • 4 BR/3 BA, 1 half bath House (sleeps 8)
    $500 - $900/nt
    $3,000 - $5,000/wk
    per property, pets considered, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

St. Leonard Charming home with bay views just short walk to the beach.

  • 3 BR/3 BA, 1 half bath House (sleeps 8)
    $200/nt
    $1,100/wk
    per property, Beach, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

North East Water front home with 200 ft. Dock and boat slip

  • 4 BR/2 BA, 1 half bath House (sleeps 10)
    $350/nt
    River, Air Conditioning, Internet, Satellite / Cable, DVD Player

Church Creek 6.5 Acre Waterfront Retreat!

  • 3 BR/2 BA House (sleeps 9)
    $621 - $650/nt
    $4,350/wk
    per property, pets considered, limited accessibility, Beach, River, Waterfront, Private Pool, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable

Deal Island New renovation of home w/garden, on water w/great Chesapeake Bay views

  • 2 BR/1 BA House (sleeps 5)
    $850/wk
    per property, accept credit card, pets considered, Hot Tub, Beach, Waterfront, Jacuzzi, Lawn / Garden, Air Conditioning, Internet

Cambridge Almost new, private waterfront - dock, beach, private pool & more

  • 6 BR/5 BA House (sleeps 16)
    $449 - $741/nt
    $2,990 - $5,190/wk
    per property, accept credit card, pets considered, Beach, Near The Ocean, River, Town, Waterfront, Private Pool, Jacuzzi, Lawn / Garden, terrace, Balcony
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