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Chesapeake Bay Rentals, Sleeps 5-8

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

  • 3 BR/2 BA House (sleeps 8)
    $95 - $155/nt
    $600 - $895/wk
    per property, accept credit card, pets considered, Rural, Village, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

St. Michaels Sea Glass Cottage on the Bay! Location! Views! MAY bookings 3 + days discount

  • 3 BR/1 BA, 1 half bath Cottage (sleeps 6)
    $275 - $400/nt
    $1,800 - $2,700/wk
    $6,000/month
    per property, Beach, Near The Ocean, Village, Waterfront, Communal Pool, Lawn / Garden, terrace, Air Conditioning, Satellite / Cable, Television, DVD Player

St. Leonard New,Quiet, Fun, Beachy, Colorful,Comfortable, Views,Economical,accessible apt

  • 2 BR/1 BA Apartment (sleeps 6)
    $125 - $225/nt
    $700 - $900/wk
    per property, accept credit card, pets considered, wheelchair accessible, Beach, Rural, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable

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

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

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

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 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

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

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

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

St. Michaels Private cottage just one mile to St. Michaels. Great for kayaking and biking!

  • 3 BR/3 BA Cottage (sleeps 6)
    $502 - $721/nt
    $2,104 - $3,219/wk
    per property, pets considered, Waterfront, Communal Pool, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

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

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

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

Cambridge Cozy waterfront cottage with hot tub, large screened porch and scenic views

  • 3 BR/1 BA Cottage (sleeps 5)
    $190 - $250/nt
    $1,075/wk
    per property, Hot Tub, Rural, Waterfront, Jacuzzi, Lawn / Garden, Air Conditioning, Television, DVD Player, Parking

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

Crisfield Spectacular Corner Unit - Direct Waterfront Condo in Crisfield, Md

  • 3 BR/2 BA Condo (sleeps 6)
    $100 - $200/nt
    $600 - $1,200/wk
    per property, accept credit card, Village, Waterfront, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Tyaskin Waterfront Chesapeake Bay Retreat.

  • 3 BR/1 BA Cottage (sleeps 6)
    $150 - $193/nt
    $950 - $1,350/wk
    $3,000 - $4,800/month
    per property, accept credit card, Beach, Waterfront, Air Conditioning, Satellite / Cable, DVD Player, Fireplace

Port Republic Chesapeake Bayfront Cottage - Port Republic, Calvert County, MD

  • 2 BR/1 BA Cottage (sleeps 6)
    $214 - $248/nt
    $1,095 - $1,495/wk
    per property, Beach, Rural, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, barbecue

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

Crisfield Waterfront luxury, natural beauty, peace and tranquility

  • 3 BR/2 BA Condo (sleeps 6)
    $100 - $225/nt
    $1,300/wk
    per property, wheelchair accessible, Downtown, Waterfront, Private Pool, terrace, Balcony, Air Conditioning, Satellite / Cable, Television

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

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

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

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

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

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

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

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 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

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

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

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. 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

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

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

Crisfield Luxury Waterfront Condo With Private Boat Slip In Crisfield Maryland

  • 3 BR/2 BA Condo (sleeps 6) wheelchair accessible, Resort, Waterfront, Jacuzzi, Balcony, Air Conditioning, Satellite / Cable, Television, DVD Player
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