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Chesapeake Bay Vacation Rentals for Golf Vacations

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SPECIAL OFFER! Spring Discount: $200 Off Regular Rates April 22 - May 21

St. Michaels *****10% off stays of 3 nights or more for April and May******

  • 3 BR/2 BA, 1 half bath Estate (sleeps 9)
    $350 - $600/nt
    $2,400 - $3,750/wk
    $9,600 - $16,020/month
    per property, pets considered, Hot Tub, limited accessibility, Rural, Waterfront, Private Pool, Lawn / Garden, Fitness Room / Equipment, Air Conditioning

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

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

St. Michaels Bay Cottage, St. Michaels, Md Waterfront Vacation Retreat: Pool, Dock,Farm, Bike

  • 6 BR/5 BA, 1 half bath Estate (sleeps 12)
    $759 - $1,419/nt
    $4,050 - $6,350/wk
    $12,150 - $19,050/month
    per property, Resort, Rural, Village, Private Pool, Lawn / Garden, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable, Television

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 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

Tilghman Island Cozy winter hideaway with wide water views and new kitchen

  • 2 BR/1 BA, 1 half bath Cottage (sleeps 4)
    $425 - $581/nt
    $1,670 - $2,537/wk
    per property, pets considered, Near The Ocean, Waterfront, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Fireplace

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. Leonard Chesapeake Bay retreat on Flag Harbor Marina. Fantastic!

  • 4 BR/2 BA House (sleeps 10)
    $250 - $300/nt
    $1,470/wk
    per property, accept credit card, pets considered, Beach, Waterfront, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

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 St Michaels Extraordinary Waterfront home on 54 acres with pool, dock, beach...

  • 5 BR/5 BA, 1 half bath House (sleeps 10)
    $1,500/nt
    $8,000/wk
    per property, pets considered, River, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

St. Michaels Incredible Waterfront Home 'Wye Provence' ' With Pool And Dock

  • 5 BR/3 BA, 1 half bath House (sleeps 10)
    $850/nt
    $5,250/wk
    per property, pets considered, River, Rural, Private Pool, Lawn / Garden, Balcony, 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)
    $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

St. Michaels Magnificent 6500 sq ft estate vacation home 'The Tred Avon Manor'

  • 7 BR/5 BA House (sleeps 12)
    $1,143 - $1,200/nt
    $7,000 - $8,000/wk
    per property, pets considered, River, Rural, Waterfront, Private Pool, Lawn / Garden, terrace, Balcony, Air Conditioning, Internet

St. Michaels 'Sandy Pines' 4 BR on Harris Creek w/Pool, Dock, Paddle boards, Kayaks, Sunfish

  • 4 BR/3 BA House (sleeps 10)
    $375 - $657/nt
    $2,600 - $4,600/wk
    per property, River, Waterfront, Private Pool, Lawn / Garden, terrace, Air Conditioning, Internet, Satellite / Cable, Television

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

  • 4 BR/2 BA House (sleeps 9)
    $200 - $565/nt
    $1,800 - $2,800/wk
    per property, accept credit card, River, Waterfront, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

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

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

Oxford Historic Oxford Waterfront Estate welcoming 1-2 couples OR up to 12 guests

  • 6 BR/5 BA, 1 half bath Estate (sleeps 12)
    $350 - $750/nt
    $2,450 - $4,900/wk
    per property, Private Pool, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, 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

St. Michaels Exceptional Waterfront Estate

  • 5 BR/6 BA, 2 half baths Estate (sleeps 10)
    $5,500/wk
    per property, pets considered, Hot Tub, Beach, Downtown, Resort, River, Rural, Town, Village, Waterfront, Private Pool, Jacuzzi, Lawn / Garden, terrace, Balcony

Port Republic Spacious beachfront getaway overlooking Chesapeake Bay

  • 3 BR/2 BA House (sleeps 10)
    $300/nt
    $1,750/wk
    per property, pets considered, Beach, Waterfront, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

Cambridge Welcome Home to Sunset Bay

  • 5 BR/3 BA, 1 half bath House (sleeps 13)
    $750/nt
    $4,900 - $5,250/wk
    $21,000 - $21,000/month
    per property, Waterfront, Private Pool, Balcony, Air Conditioning, Satellite / Cable, Television, DVD Player, Parking

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

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

Cobb Island Enjoy the Water? Fishing, Crabbing, Boating? Here it is!

  • 4 BR/2 BA, 1 half bath House (sleeps 9)
    $2,030/wk
    $6,750/month
    per property, accept credit card, pets considered, River, Rural, Waterfront, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

St. Leonard Osprey's Nest, Spacious, Peaceful, Bay Views, Sunrises, Relaxing

  • 4 BR/3 BA House (sleeps 10)
    $357 - $400/nt
    $2,000 - $2,500/wk
    per property, accept credit card, pets considered, wheelchair accessible, Beach, Rural, Balcony, 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)
    $350 - $400/nt
    $1,700 - $2,000/wk
    per property, accept credit card, pets considered, Beach, Near The Ocean, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

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

St. Michaels Luxurious and Extremely Private Waterfront Estate

  • 8 BR/7 BA, 2 half baths Estate (sleeps 20)
    $1,200/nt
    $7,450 - $11,500/wk
    per property, pets considered, Rural, Waterfront, Private Pool, Tennis Court, Lawn / Garden, terrace, Balcony, Air Conditioning

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

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

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

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
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