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Chesapeake Bay 4+ BR Rentals

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Oxford Updated Historic Sprawling Waterfront Estate minutes to Oxford

  • 5 BR/3 BA House (sleeps 10)
    $717 - $993/nt
    $3,416 - $4,900/wk
    per property, Near The Ocean, Rural, Village, Private Pool, pets considered, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

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

  • 5 BR/3 BA, 1 half bath House (sleeps 10) River, Rural, Private Pool, Lawn / Garden, Balcony, pets considered, Air Conditioning, 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) wheelchair accessible, Downtown, River, Town, Waterfront, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

St. Michaels St Michaels Premier Waterfront home with pool and dock

  • 5 BR/4 BA House (sleeps 10) River, Private Pool, Lawn / Garden, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

St. Michaels Exquisite 360 acre farm with 5 bedroom Manor, pool and vineyard

  • 5 BR/3 BA, 1 half bath House (sleeps 10) Rural, Waterfront, Lawn / Garden, Balcony, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

St. Michaels 'Chez Bonheur' magnificent 5 bedroom home on 1000 acre estate with pool and dock

  • 6 BR/2 BA, 2 half baths House (sleeps 6)
    $7,000/wk
    per property, River, Rural, Waterfront, Private Pool, terrace, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

North East Unique Waterfront Home with Breathtaking Views

  • 6 BR/3 BA, 1 half bath House (sleeps 11)
    $440/nt
    $2,950/wk
    per property, Beach, River, Rural, Waterfront, Lawn / Garden, pets considered, DVD Player

St. Michaels Luxury St. Michaels Waterfront 6 Bedrooms/6 Baths $4900/Week

  • 6 BR/6 BA, 2 half baths House (sleeps 12)
    $4,900/wk
    per property, accept credit card, Beach, Downtown, Resort, River, Rural, Town, Village, Waterfront, Private Pool, Jacuzzi, Lawn / Garden, terrace, Balcony, Air Conditioning

Betterton Charming home in beach community in Upper Eastern Shore on Chesapeake Bay

  • 6 BR/2 BA House (sleeps 8)
    $200/nt
    $1,200/wk
    per property, Beach, Town, pets considered, Television, DVD Player, Parking, Fireplace

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

  • 4 BR/2 BA, 1 half bath House (sleeps 8)
    $650 - $700/nt
    $2,950 - $3,150/wk
    per property, accept credit card, wheelchair accessible, River, Waterfront, Communal Pool, Lawn / Garden, Balcony, pets considered, Air Conditioning
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Deale Million Dollar View on the Chesapeake Bay

  • 4 BR/3 BA House (sleeps 10)
    $250 - $300/nt
    $1,500 - $1,900/wk
    per property, Waterfront, Jacuzzi, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

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

  • 7 BR/3 BA, 1 half bath House (sleeps 18) wheelchair accessible, River, Rural, Waterfront, Lawn / Garden, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

St. Michaels Premier Waterfront Vacation Home/St. Michaels (Sept./Oct. Availability)

  • 4 BR/4 BA House (sleeps 8)
    $2,200/wk
    per property, accept credit card, limited accessibility, Rural, Waterfront, Communal Pool, Jacuzzi, Sauna, Lawn / Garden, Air Conditioning

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

  • 4 BR/2 BA, 1 half bath House (sleeps 9)
    $2,200/wk
    per property, accept credit card, River, Rural, Waterfront, Lawn / Garden, Balcony, pets considered, Air Conditioning, Internet, Satellite / Cable

St. Michaels Luxury Waterfront Home....ONE SUMMER WEEK LEFT 6/23-6/30

  • 5 BR/4 BA House (sleeps 10)
    $650 - $800/nt
    $3,500 - $6,500/wk
    per property, Town, Waterfront, Private Pool, Lawn / Garden, terrace, Air Conditioning, Internet, Satellite / Cable, Television

Point Lookout Luxury Chesapeake Bay Waterfront House - Enjoy Miles of Sandy Beach

  • 5 BR/5 BA House (sleeps 12)
    $2,900/wk
    per property, accept credit card, Beach, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Tilghman Island Privacy And Family Quality Time

  • 6 BR/5 BA, 1 half bath House (sleeps 15) Private Pool, pets considered, Air Conditioning, Internet, Satellite / Cable, Television, Parking, Fireplace

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

  • 4 BR/2 BA House (sleeps 8)
    $180 - $375/nt
    $1,260 - $1,960/wk
    per property, limited accessibility, Rural, Waterfront, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

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

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

St. Michaels Ultimate family vacation home! Pool, dock, games barn, hot tub and more!

  • 5 BR/4 BA House (sleeps 10)
    $1,118 - $1,185/nt
    $4,985 - $7,240/wk
    per property, Beach, Village, Private Pool, Air Conditioning, Internet, Fireplace
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St. Leonard Chesa. Bay Vacation Rental, quiet, beachy, open, bay view, LAST MIN. SPECIALS!

  • 4 BR/2 BA, 1 half bath House (sleeps 12)
    $300 - $450/nt
    $1,800 - $2,000/wk
    per property, accept credit card, Beach, Near The Ocean, Balcony, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

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

  • 4 BR/3 BA House (sleeps 10)
    $300 - $450/nt
    $2,000 - $2,500/wk
    per property, accept credit card, wheelchair accessible, Beach, Rural, Balcony, pets considered, Air Conditioning, Internet, Satellite / Cable

St. Michaels Luxurious and Extremely Private Waterfront Estate

  • 9 BR/7 BA, 2 half baths Estate (sleeps 20)
    $11,500/wk
    $39,500/month
    per property, Rural, Waterfront, Private Pool, Daily Maid Service, Tennis Court, Lawn / Garden, terrace, Balcony, pets considered

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

  • 4 BR/5 BA House (sleeps 10)
    $4,500 - $6,500/wk
    per property, accept credit card, River, Rural, Village, Waterfront, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

Cambridge Welcome Home to Sunset Bay

  • 5 BR/3 BA, 1 half bath House (sleeps 13) Waterfront, Private Pool, Jacuzzi, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

North East Top of the Chesapeake - Minutes from Historic Charlestown

  • 5 BR/2 BA House (sleeps 11)
    $359 - $429/nt
    $2,499 - $2,699/wk
    per property, accept credit card, River, Waterfront, Balcony, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

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

  • 4 BR/2 BA House (sleeps 9)
    $285/nt
    $2,000 - $2,350/wk
    per property, accept credit card, River, Waterfront, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

Port Republic Private Beachfront Home with Beautiful Bay View

  • 4 BR/2 BA House (sleeps 12)
    $2,300/wk
    per property, accept credit card, Beach, Waterfront, Communal Pool, Tennis Court, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable

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

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

Tilghman Island In the Heart of Chesapeake Bay on Maryland’s Scenic Eastern Shore

  • 7 BR/7 BA, 1 half bath House (sleeps 14)
    $2,000 - $2,500/wk
    per property, Beach, Downtown, Near The Ocean, Resort, Town, Village, Waterfront, Lawn / Garden, pets considered, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player
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Chesapeake Beach Chesapeake Beach House -- 30 Miles from DC or Annapolis Md

  • 6 BR/5 BA, 1 half bath House (sleeps 13)
    $850 - $875/nt
    $5,000 - $5,500/wk
    per property, accept credit card, Beach, Town, Waterfront, Jacuzzi, terrace, Balcony, pets considered, Air Conditioning, Internet

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

  • 6 BR/5 BA House (sleeps 16) accept credit card, Beach, Near The Ocean, River, Town, Waterfront, Private Pool, Jacuzzi, Lawn / Garden, terrace, Balcony, pets considered

St. Michaels Relaxing Waterfront Estate - 7 Bedrooms/Indoor Pool

  • 7 BR/6 BA House (sleeps 20) Waterfront, Air Conditioning, Internet, Satellite / Cable, Television, barbecue, Fireplace

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

  • 4 BR/2 BA House (sleeps 10) accept credit card, Beach, Waterfront, pets considered, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Cambridge Sprawling Multi-Family Home with all the best amenities--pool, hot tub, dock, kayaks and more!

  • 6 BR House (sleeps 23) Town, Waterfront, Air Conditioning

St. Michaels Chesapeak Bay oriented waterfront home with private pool and deep water dock

  • 4 BR/3 BA, 1 half bath House (sleeps 8) accept credit card, Balcony, Internet, Satellite / Cable, Television, DVD Player, barbecue, Fireplace

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

  • 4 BR/4 BA Estate (sleeps 8) Rural, Waterfront, Private Pool, Jacuzzi, Lawn / Garden, terrace, Balcony, Air Conditioning, Internet

Chestertown Historic House, Steps to Shopping, Dining and Chester River

  • 4 BR/2 BA, 1 half bath House (sleeps 8) Downtown, River, Balcony, Air Conditioning, Internet, 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, Waterfront, Private Pool, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

St. Michaels Large Waterfront Estate Located on Miles River

  • 6 BR/4 BA House (sleeps 12) accept credit card, Waterfront, Satellite / Cable, Television, DVD Player, barbecue
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St. Michaels Willows on the Miles - Private, waterfront farmhouse estate- Miles River

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

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

St. Leonard Chesapeake Bay Luxury Vacation/Rental Home

  • 6 BR/3 BA House (sleeps 12) Beach, Resort, Communal Pool, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

Betterton Beautiful Estate + Organic Farm + Pool on 20 acres

  • 4 BR/2 BA, 1 half bath Farmhouse (sleeps 16) Rural, Private Pool, Lawn / Garden, pets considered, Air Conditioning, Internet, Television, DVD Player

Church Creek Warm, Welcoming Waterfront, Relaxing and Close to Everything

  • 5 BR/2 BA, 1 half bath Farmhouse (sleeps 18) Rural, Waterfront, Communal Pool, pets considered, Air Conditioning, Satellite / Cable, Television, Parking, barbecue

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

  • 4 BR/4 BA House (sleeps 8) accept credit card, wheelchair accessible, Beach, Waterfront, Jacuzzi, Balcony, Air Conditioning, Satellite / Cable, Television

Cambridge Serenity Acres - Waterfront, 23 Private Acres, Dock W/Slips & Pool

  • 4 BR/3 BA, 1 half bath House (sleeps 17)
    $600/nt
    $3,700/wk
    per property, River, Waterfront, Private Pool, Lawn / Garden, Air Conditioning, Satellite / Cable, Television, DVD Player, Parking

Deal Island Elegant, waterview, brand new villa by the Chesapeake Bay

  • 4 BR/3 BA House (sleeps 10)
    $250/nt
    $1,100 - $1,500/wk
    per property, accept credit card, Beach, Rural, Lawn / Garden, Balcony, pets considered, Air Conditioning, Internet, Satellite / Cable

Cambridge Bayberry Cove Private 11 Acre Chesapeake Waterfront 5 Bedroom w/Pool & Hot Tub

  • 5 BR/4 BA House (sleeps 15)
    $500/nt
    $3,100 - $3,950/wk
    per property, accept credit card, River, Rural, Private Pool, Jacuzzi, pets considered, Air Conditioning, Internet, Satellite / Cable

St. Michaels St. Michaels Premier Waterfront estate close to town, golfcourse, Harbor,Museum

  • 6 BR/5 BA, 1 half bath Estate (sleeps 12) accept credit card, Resort, Waterfront, Private Pool, Jacuzzi, Lawn / Garden, Balcony, Air Conditioning, Internet
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