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Chesapeake Bay Rentals

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Oxford Updated Historic Sprawling Waterfront Estate minutes to Oxford

  • 5 BR/3 BA House (sleeps 10)
    $595 - $865/nt
    $3,035 - $5,235/wk
    per property, Near The Ocean, Rural, Village, Private Pool, pets considered, Air Conditioning, Internet, Fireplace

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

  • 5 BR/4 BA House (sleeps 10)
    $1,020 - $1,776/nt
    $4,985 - $6,635/wk
    per property, Beach, Village, Private Pool, Air Conditioning, Internet, Fireplace

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

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

  • 4 BR/2 BA, 1 half bath House (sleeps 8)
    $400 - $700/nt
    $1,950 - $3,150/wk
    per property, accept credit card, wheelchair accessible, River, Waterfront, Communal Pool, Lawn / Garden, Balcony, pets considered, Air Conditioning

Port Republic Treasure the Chesapeake Bay w/Beachfront Home

  • 3 BR/2 BA House (sleeps 6)
    $1,950/wk
    per property, Beach, Waterfront, Communal Pool, Tennis Court, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

St. Michaels 2 Weeks Still Open in June - $2000 Off $6300/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

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

  • 3 BR/3 BA Cottage (sleeps 6)
    $590 - $760/nt
    $2,270 - $2,934/wk
    $8,745/month
    per property, Waterfront, pets considered, Air Conditioning, Internet, Fireplace

St. Michaels Luxury Waterfront Home, Sunsets, Pool, 2 miles from Town Center!

  • 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

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

  • 2 BR/1 BA, 1 half bath Cottage (sleeps 4)
    $392 - $450/nt
    $1,590 - $2,150/wk
    $5,925/month
    per property, Near The Ocean, Waterfront, pets considered, Air Conditioning, Internet, Fireplace

St. Michaels Endless Waterfront Sunsets on Eastern Bay!!

  • 3 BR/3 BA, 1 half bath House (sleeps 8)
    $300 - $550/nt
    $1,900 - $3,000/wk
    per property, accept credit card, River, Rural, Village, Waterfront, Communal Pool, Jacuzzi, Lawn / Garden, Balcony, Air Conditioning, Internet
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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

Port Republic Magical Bayfront Home

  • 3 BR/2 BA House (sleeps 8) accept credit card, limited accessibility, wheelchair accessible, Beach, Waterfront, pets considered, Air Conditioning, Internet, Satellite / Cable

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

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 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 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

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

Cambridge Fishing Cove Private Waterfront Retreat with Pool and Pier

  • 8 BR/6 BA House (sleeps 22) accept credit card, limited accessibility, wheelchair accessible, Waterfront, Private Pool, Jacuzzi, Balcony, pets considered
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