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Chesapeake Bay Vacation Rental Lodging - Page 2 of 3

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North East Cozy Cottage with Vaulted Ceiling, minutes from Main St cafes and shops

  • 1 BR/1 BA Cottage (sleeps 4)
    $109 - $129/nt
    $779 - $799/wk
    $2,799 - $2,999/month
    per property, pets considered, Village, Lawn / Garden, Air Conditioning, Satellite / Cable, Television, Parking

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

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

Deal Island Relaxing Sunset and Water View Cottage

  • 2 BR/1 BA Cottage (sleeps 5)
    $100 - $150/nt
    $600 - $850/wk
    per property, pets considered, Beach, Waterfront, Air Conditioning, Satellite / Cable, Television, DVD Player, Parking, barbecue

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

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

St. Leonard Harbor Cottage at the Chesapeake Bay Vacation Rental

  • 2 BR/2 BA Cottage (sleeps 6)
    $260/nt
    $1,120/wk
    per property, accept credit card, pets considered, Beach, Waterfront, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television

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

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 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

North Beach Reserve Your Long Overdue Vacation On the Chesapeake Today With a Sandy Beach !

  • 2 BR Cottage (sleeps 4)
    $350/nt
    per property, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television, Parking

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 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

Solomons Island Extended Stay for Solomons Island, Pax River NAS and Calvert Cliffs NPP

  • 2 BR/2 BA Condo (sleeps 4)
    $2,790 - $4,650/month
    per property, wheelchair accessible, Communal Pool, Balcony, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable, Television

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

Deale The True 'Bay Life'

  • 3 BR/1 BA Cottage (sleeps 5)
    $225/nt
    $1,000/wk
    per property, pets considered, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

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

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

  • 7 BR/6 BA House (sleeps 20)
    $700 - $1,000/nt
    $4,900/wk
    per property, Waterfront, Air Conditioning, Internet, Satellite / Cable, Television, barbecue, Fireplace

Cambridge Chesapeake Bay Nature-Oriented Recreation & Repose

  • 3 BR/2 BA House (sleeps 6) accept credit card, pets considered, River, Jacuzzi, terrace, Air Conditioning, Satellite / Cable, Television

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

St. Michaels Large Elegant Ralph Lauren Waterfront Cottage Nr St Michaels with Georgous views

  • 3 BR/2 BA Cottage (sleeps 6) accept credit card, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television, Parking, barbecue

Cambridge Heron's View Vacation Rental in the Heart of Chesapeake Country!

  • 3 BR/2 BA House (sleeps 6) pets considered, Hot Tub, Town, Waterfront, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Cambridge Luxury Waterfront Condo on Chesapeake Hyatt Property

  • 2 BR/2 BA Condo (sleeps 6) accept credit card, wheelchair accessible, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable

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

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

Tilghman Island Tilghman Island Dreamin. A Beautiful Home Overlooking Dogwood Harbor

  • 4 BR/2 BA, 1 half bath Villa (sleeps 10) pets considered, Waterfront, Jacuzzi, Balcony, Air Conditioning, Satellite / Cable, Television, DVD Player

Crisfield Chesapeake Waterfront with Private Dock in Crisfield, Maryland

  • 2 BR/1 BA House (sleeps 6) accept credit card, Town, Waterfront, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

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

  • 6 BR/2 BA House (sleeps 8) pets considered, Beach, Town, Television, DVD Player, Parking, Fireplace

Elkton Elk River Vacation Rental (Quiet, Open, Relaxing River Front)

  • 3 BR/1 BA, 1 half bath Cabin (sleeps 8) accept credit card, pets considered, River, Waterfront, Air Conditioning, 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) pets considered, Rural, Private Pool, Lawn / Garden, 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) pets considered, Rural, Waterfront, Communal Pool, Air Conditioning, Satellite / Cable, Television, Parking, barbecue

St. Leonard Chesapeake Bay fossil hunting from your own front yard! 50 min. D.C

  • 3 BR/1 BA Cottage (sleeps 6) Beach, Waterfront, Air Conditioning, Internet, Satellite / Cable, Television, 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

St. Leonard Chesapeake Bay Cottage

  • 2 BR/1 BA House (sleeps 8)
    $90 - $150/nt
    $540 - $900/wk
    $2,160 - $3,600/month
    per property, Lawn / Garden, Internet, Satellite / Cable, Television, DVD Player, Parking

Deal Island Elegant, waterview, villa by the Chesapeake Bay

  • 4 BR/3 BA House (sleeps 10)
    $214 - $250/nt
    $1,250 - $1,500/wk
    per property, accept credit card, pets considered, Beach, Rural, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

Betterton Comfortable, very clean and well-equipped home near Chesapeake Bay.

  • 3 BR/2 BA House (sleeps 6)
    $125 - $205/nt
    $615 - $1,230/wk
    per property, pets considered, Beach, Town, Air Conditioning, Television, DVD Player, Parking

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

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

Deal Island Water Water Everywhere!

  • 3 BR/2 BA House (sleeps 8)
    $1,400/wk
    $4,500/month
    per property, pets considered, Beach, Downtown, Lake, Near The Ocean, River, Rural, Waterfront, Lawn / Garden, Balcony, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable

Tilghman Island 'Knapp Shack'-Waterfront townhome overlooking the Bay

  • 3 BR/2 BA, 1 half bath House (sleeps 6)
    $250 - $300/nt
    $1,505 - $1,855/wk
    per property, accept credit card, pets considered, Waterfront, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

St. Michaels Waterfront Country Cottage Close To St Michaels

  • 3 BR/3 BA Cottage (sleeps 6)
    $280 - $495/nt
    $1,908 - $2,520/wk
    per property, Village, Waterfront, terrace, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking
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