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Chesapeake Bay Vacation Rentals for Golf Vacations

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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 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

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

  • 2 BR/1 BA Apartment (sleeps 6)
    $150/nt
    $700 - $800/wk
    per property, accept credit card, wheelchair accessible, Beach, Rural, Lawn / Garden, pets considered, Air Conditioning, Internet, Satellite / Cable

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

Port Republic Spacious beachfront getaway overlooking Chesapeake Bay

  • 3 BR/2 BA House (sleeps 10) Beach, Waterfront, pets considered, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

St. Leonard Hidden Cove Apartment resting on the Shores of Wells Cove

  • 1 BR/1 BA House (sleeps 2)
    $90 - $125/nt
    per property, Beach, Waterfront, pets considered, Air Conditioning, Internet, Television, Parking

Tyaskin Nanticoke Farmhouse - Luxury and Charm at the Chesapeake Bay

  • 3 BR/2 BA, 1 half bath House (sleeps 6) Beach, River, Lawn / Garden, pets considered, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

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

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

  • 3 BR/3 BA Cottage (sleeps 6)
    $490 - $760/nt
    $1,970 - $3,140/wk
    $7,545 - $8,745/month
    per property, Waterfront, pets considered, Air Conditioning, Internet, Fireplace

Crisfield Waterfront luxury, natural beauty, peace and tranquility

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

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 3 Free Kayaks To Explore the Bay Included

  • 4 BR/3 BA Cottage (sleeps 8)
    $458 - $562/nt
    $1,975 - $2,290/wk
    $7,225/month
    per property, Downtown, Rural, Waterfront, Air Conditioning, Internet, Fireplace

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

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

Deal Island Chesapeake Bay-Deal Island Vacation Bay views- fishing-crabbing -boating

  • 3 BR/2 BA House (sleeps 8)
    $110 - $150/nt
    $750 - $895/wk
    $2,800 - $3,500/month
    per property, Village, Waterfront, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

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 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 Europa on the Beach - Architectural contemporary home on the Chesapeake Bay

  • 3 BR/2 BA House (sleeps 6) Waterfront, Private Pool, Lawn / Garden, terrace, Balcony, Air Conditioning, Internet, Satellite / Cable

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
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Oxford Updated Historic Sprawling Waterfront Estate minutes to Oxford

  • 5 BR/3 BA House (sleeps 10)
    $595 - $942/nt
    $3,035 - $5,960/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 - $1,185/nt
    $4,985 - $6,635/wk
    per property, Beach, Village, Private Pool, Air Conditioning, Internet, Fireplace

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

  • 4 BR/2 BA House (sleeps 9)
    $1,950 - $2,450/wk
    per property, accept credit card, River, Waterfront, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

Port Republic Stone's Throw - Bayfront Log Cabin with 180 degree View in Exclusive Community

  • 2 BR/1 BA House (sleeps 5)
    $180 - $300/nt
    $1,100 - $1,500/wk
    per property, accept credit card, Beach, Resort, Rural, Waterfront, Communal Pool, Tennis Court, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable

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
    $1,700 - $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

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

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

Solomons Island Cedar Beach Lodge is a Modern Year-Round Retreat on the Chesapeake Bay

  • 3 BR/2 BA House (sleeps 8)
    $350/nt
    $1,850/wk
    per property, accept credit card, Beach, Rural, Waterfront, Lawn / Garden, pets considered, Air Conditioning, Internet, Satellite / Cable, Television
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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

Port Republic Private Beachfront Home with Beautiful Bay View

  • 4 BR/2 BA House (sleeps 12)
    $1,600 - $2,300/wk
    per property, accept credit card, Beach, Waterfront, Communal Pool, Tennis Court, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable

North Beach Relaxing House on Chesapeake Bay

  • 3 BR/2 BA, 1 half bath House (sleeps 8) Waterfront, Balcony, Air Conditioning, Satellite / Cable, Television, DVD Player, barbecue, Fireplace

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

St. Michaels New listing with rural country charm, pool, and a deep water dock

  • 3 BR/2 BA, 1 half bath Estate (sleeps 10) limited accessibility, Rural, Waterfront, Private Pool, Lawn / Garden, pets considered, Fitness Room / Equipment, Air Conditioning, Internet

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

St. Michaels Premier Waterfront Vacation Home/St. Michaels (August 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

North East Life On The Water

  • 3 BR/3 BA House (sleeps 8) limited accessibility, River, Waterfront, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

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

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
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North Beach Herrington Harbour - Beautiful Single Family Home - Rose Haven

  • 3 BR/2 BA House (sleeps 7)
    $275/nt
    $1,300/wk
    per property, accept credit card, Resort, Waterfront, Private Pool, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

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

Tilghman Island Charming and elegant with a water view of Knapps Narrows

  • 3 BR/2 BA House (sleeps 6)
    $300/nt
    $1,800/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 24) accept credit card, wheelchair accessible, Beach, Waterfront, Jacuzzi, Balcony, 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

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

Church Creek 6.5 Acre Waterfront Retreat!

  • 3 BR/2 BA House (sleeps 9) limited accessibility, Beach, River, Waterfront, Private Pool, Lawn / Garden, pets considered, Air Conditioning, Internet, Satellite / Cable

Oxford Oxford Apartment with B&B amenities including waterfront lawn and private beach.

  • 1 BR/1 BA Lodge (sleeps 2) accept credit card, Beach, River, Rural, Town, Village, Waterfront, Daily Maid Service, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television

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, Beach, Waterfront, Jacuzzi, Lawn / Garden, pets considered, Air Conditioning, Internet, Satellite / Cable

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
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