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Chesapeake Bay Accommodations Vacation Cottages

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Tilghman Island 1920's Restored Waterman's Cottage with Fantastic Views!

  • 2 BR/1 BA, 1 half bath Cottage (sleeps 4)
    $392 - $500/nt
    $1,590 - $2,189/wk
    $5,925/month
    per property, Near The Ocean, Waterfront, pets considered, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

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

  • 2 BR/1 BA Cottage (sleeps 6) Beach, Rural, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, barbecue

St. Michaels Sea Glass Cottage on the Bay - St Michaels MD Area

  • 3 BR/1 BA, 1 half bath Cottage (sleeps 6)
    $300 - $400/nt
    $2,000 - $2,700/wk
    per property, Beach, Near The Ocean, Village, Waterfront, Communal Pool, Lawn / Garden, terrace, Air Conditioning, 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) Rural, Waterfront, Jacuzzi, Lawn / Garden, Air Conditioning, Television, DVD Player, Parking

St. Michaels Private Cottage just outside St. Michaels with kayak and bikes included!

  • 3 BR/3 BA Cottage (sleeps 6)
    $473 - $610/nt
    $2,002 - $2,783/wk
    $7,545/month
    per property, Waterfront, pets considered, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Point Lookout Renovated cottage with Chesapeake Bay sandy beach direct access

  • 1 BR/1 BA Cottage (sleeps 3)
    $800 - $990/wk
    per property, accept credit card, Beach, Rural, pets considered, Air Conditioning, Internet, Satellite / Cable, DVD Player

Chestertown Chester River Water Front Retreat - Sunrise and Sunset Views

  • 3 BR Cottage (sleeps 8)
    $350 - $400/nt
    $2,100/wk
    $8,000/month
    per property, River, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

Tyaskin Waterfront Chesapeake Bay Retreat.

  • 3 BR/1 BA Cottage (sleeps 6)
    $950 - $1,350/wk
    $4,400/month
    per property, accept credit card, Beach, Waterfront, Air Conditioning, Satellite / Cable, DVD Player, Fireplace

Deale The True 'Bay Life'

  • 3 BR/1 BA Cottage (sleeps 6) Lawn / Garden, pets considered, Air Conditioning, Internet, 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
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St. Leonard Harbor Cottage at the Chesapeake Bay Vacation Rental

  • 2 BR/2 BA Cottage (sleeps 6)
    $780 - $1,110/wk
    per property, accept credit card, Beach, Waterfront, Lawn / Garden, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

St. Michaels Waterfront Country Cottage Close To St Michaels

  • 3 BR/3 BA Cottage (sleeps 6) Village, Waterfront, terrace, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

St. Michaels St. Michael's premier in town summer vacation cottage!

  • 2 BR/2 BA Cottage (sleeps 4) Beach, Downtown, Communal Pool, Lawn / Garden, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

Tilghman Island Tilghman Island Cottage for Six

  • 3 BR/2 BA Cottage (sleeps 6)
    $850/wk
    per property, limited accessibility, Near The Ocean, Rural, Town, Communal Pool, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

Deal Island Vintage Waterfront Cottage with Fishing Pier on the Chesapeake Bay.

  • 2 BR/1 BA Cottage (sleeps 5) Beach, Rural, pets considered, Internet, Satellite / Cable, Television, DVD Player

North Beach HERON'S REST GUEST COTTAGE - Your Slice of Paradise!!

  • 1 BR/1 BA Cottage (sleeps 4) accept credit card, Beach, Near The Ocean, Air Conditioning, Internet, Satellite / Cable, Television
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