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Chesapeake Bay Vacation Rental Accommodations - Page 1 of 2

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SPECIAL OFFER! Fall Getaway Special 40% off peak rates October 28 - December 23

St. Leonard Spacious,Peaceful,Comfort. Bay View,Eagles,Osprey,Sunrises from deck,Beaches

  • 4 BR/3 BA House (sleeps 8)
    $250 - $500/nt
    $2,000 - $2,500/wk
    $5,000 - $6,500/month
    per property, beach, rural, balcony, pets considered, air-conditioning, internet access, satellite or cable, TV, DVD
SPECIAL OFFER! $500 Fall Weekend Getaway special!!! October 28 - December 21

St. Leonard Chesapeake Bay Vacation Rental, quiet, beachy, open, bay view

  • 4 BR/2 BA, 1 half bath House (sleeps 12)
    $250 - $300/nt
    $1,200 - $1,500/wk
    per property, beach, near the ocean, balcony, pets considered, air-conditioning, internet access, satellite or cable, TV, DVD

North Beach New House on Chesapeake Bay

  • 3 BR/2 BA, 1 half bath House (sleeps 8)
    $1,100/wk
    per property, waterfront, balcony, air-conditioning, satellite or cable, TV, DVD, barbecue, fireplace

St. Michaels Adorable and Cozy Cape with wide water views, minutes to St. Michaels

  • 3 BR/3 BA Cottage (sleeps 7)
    $1,350 - $2,250/wk
    per cottage, dock boatslip, DVD, fireplace, grill, linens provided, pets not allowed, Fully Equipped Kitchen

St. Michaels One level vacation home outside St. Michaels, pool, wide views, great breezes

  • 3 BR/3 BA House (sleeps 8)
    $1,744 - $3,773/wk
    per house, DVD, fireplace, grill, linens provided, pets, private pool, Fully Equipped Kitchen

St. Michaels Charming cottage with great sunsets, cozy fireplaces and patios.

  • 3 BR/2 BA Cottage (sleeps 7)
    $1,419 - $2,319/wk
    per cottage, dock boatslip, DVD, fireplace, grill, linens provided, pets, Fully Equipped Kitchen

St. Michaels Upscale home outside St. Michaels, pool, dock, newly renovated kitchen and baths, a fabulous retreat

  • 6 BR/3 BA House (sleeps 11)
    $2,850 - $5,362/wk
    per house, dock boatslip, DVD, fireplace, grill, linens provided, pets, private pool, Fully Equipped Kitchen

St. Michaels Classic Bay home with pool, dock, game room, just outside Easton and St. Michaels.

  • 4 BR/4 BA House (sleeps 8)
    $4,700/wk
    per house, dock boatslip, DVD, fireplace, grill, linens provided, pool table, pets not allowed, private pool

St. Michaels Waterfront cottage with pool and hot tub, close to town of St. Michaels

  • 3 BR/3 BA Cottage (sleeps 6)
    $1,401 - $2,976/wk
    per cottage, dock boatslip, DVD, fireplace, grill, indoor hot tub, linens provided, pets, private pool

St. Michaels Restored farmhouse with pool, poolhouse, dock, kayak and more!

  • 5 BR/4 BA House (sleeps 10)
    $2,895 - $5,407/wk
    per house, dock boatslip, DVD, fireplace, grill, linens provided, pets not allowed, private pool, Fully Equipped Kitchen
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Easton Close to town with country amenities! Waterfront cottage close to town, perfect for visiting relati

  • 3 BR/2 BA Cottage (sleeps 6)
    $1,186 - $2,286/wk
    per cottage, dock boatslip, DVD, fireplace, grill, linens provided, pets, private pool, Fully Equipped Kitchen

St. Michaels Hideaway on Long Haul Creek, minutes to town

  • 3 BR/3 BA Cottage (sleeps 6)
    $1,295 - $1,920/wk
    per cottage, dock boatslip, DVD, fireplace, grill, pets, Fully Equipped Kitchen, Linens with Fee

North Beach North Beach Vacation Home

  • 3 BR/2 BA, 1 half bath House (sleeps 6)
    $1,400/wk
    per property, beach, waterfront, jacuzzi, terrace, balcony, air-conditioning, DVD, parking, fireplace

St. Michaels Large Luxury Waterfront Cape Cod with New Pool and Beautiful Sunsets

  • 5 BR/4 BA House (sleeps 12)
    $3,000 - $5,850/wk
    per property, town, waterfront, pool, garden, terrace, air-conditioning, internet access, satellite or cable, TV

St. Michaels Beautifully appointed vacation home outside St. Michaels

  • 6 BR/5 BA House (sleeps 12)
    $3,251 - $5,307/wk
    per house, dock boatslip, DVD, fireplace, grill, linens provided, pool table, pets not allowed, private pool

St. Michaels Budget friendly cottage getaway, with rowboat included!

  • 4 BR/2 BA Cottage (sleeps 8)
    $1,315 - $1,940/wk
    per cottage, dock boatslip, DVD, fireplace, grill, pets, Fully Equipped Kitchen, Linens with Fee

Tilghman Island Charming Tilghman Island getaway cottage

  • 4 BR/2 BA Cottage (sleeps 8)
    $1,060 - $1,310/wk
    per cottage, DVD, fireplace, grill, indoor hot tub, pets, Fully Equipped Kitchen, Linens with Fee

St. Michaels Cottage with pool, hot tub and great water

  • 4 BR/4 BA House (sleeps 8)
    $1,704 - $3,576/wk
    per house, dock boatslip, DVD, grill, indoor hot tub, linens provided, pets not allowed, private pool, Fully Equipped Kitchen

St. Michaels Expansive 4 bedroom home 5 blocks to town of St. Michaels, wide water views.

  • 4 BR/3 BA House (sleeps 8)
    $1,265 - $2,190/wk
    per house, dock boatslip, DVD, fireplace, grill, pets, Fully Equipped Kitchen, Linens with Fee

St. Michaels Light Filled Contemporary with 4 Queen bedrooms, dock,pool

  • 4 BR/2 BA House (sleeps 9)
    $1,747 - $3,776/wk
    per house, dock boatslip, DVD, fireplace, grill, linens provided, pets, private pool, Fully Equipped Kitchen
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St. Michaels Fun house outside St. Michaels, pool, dock, hot tub, ping pong

  • 4 BR/3 BA House (sleeps 8)
    $1,473 - $3,345/wk
    per house, dock boatslip, DVD, fireplace, grill, indoor hot tub, pets, private pool, Fully Equipped Kitchen

Chestertown 4BR waterfront home outside Chestertown, wide water views!

  • 4 BR/3 BA House (sleeps 8)
    $1,253 - $1,976/wk
    per house, DVD, fireplace, grill, linens provided, pool table, pets not allowed, Fully Equipped Kitchen

St. Michaels Very private 25 acre home with sunset views, deep water dock, pool

  • 4 BR/3 BA House (sleeps 8)
    $1,653 - $3,350/wk
    per house, dock boatslip, DVD, fireplace, grill, pets, private pool, Fully Equipped Kitchen, Linens with Fee

St. Michaels Waterfront Cottage minutes to St. Michaels, hot tub

  • 3 BR/2 BA Cottage (sleeps 5)
    $1,358 - $2,158/wk
    per cottage, DVD, fireplace, grill, indoor hot tub, linens provided, pets not allowed, Fully Equipped Kitchen

St. Michaels Contemporary Cottage with pool, tranquil views and great nature watching!

  • 3 BR/2 BA Cottage (sleeps 8)
    $1,646 - $3,336/wk
    per cottage, dock boatslip, DVD, fireplace, grill, linens provided, pets, private pool, Fully Equipped Kitchen

St. Michaels Conveniently located home between Easton and St. Michaels, private with Tred Avon views!

  • 3 BR/2 BA Cottage (sleeps 6)
    $1,375 - $2,275/wk
    per cottage, dock boatslip, DVD, fireplace, grill, linens provided, pets not allowed, Fully Equipped Kitchen

St. Michaels Single family getaway! Pool, playgym, dock, and more!

  • 3 BR/1 BA Cottage (sleeps 6)
    $1,328 - $2,333/wk
    per cottage, dock boatslip, DVD, fireplace, grill, pets, private pool, Fully Equipped Kitchen

St. Michaels Bungalow in heart of historic district

  • 2 BR/2 BA Cottage (sleeps 4)
    $1,150 - $1,175/wk
    per cottage, DVD, grill, pets, Fully Equipped Kitchen, Linens with Fee

St. Michaels Historic Estate with 5BR's, pool, hot tub, gourmet kitchen and deep water dock.

  • 5 BR/4 BA House (sleeps 14)
    $2,603 - $5,878/wk
    per house, dock boatslip, DVD, fireplace, grill, indoor hot tub, linens provided, pets, private pool

Tilghman Island Tilghman Island Cottage with pool, dock, hot tub and wide views!

  • 3 BR/3 BA Cottage (sleeps 7)
    $1,353 - $2,758/wk
    per cottage, dock boatslip, DVD, grill, indoor hot tub, linens provided, pets, private pool, Fully Equipped Kitchen
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Tilghman Island Tilghman Island getaway with private dock, great views, and more!

  • 3 BR/2 BA Cottage (sleeps 6)
    $1,570/wk
    per cottage, dock boatslip, DVD, grill, pets, Fully Equipped Kitchen

St. Michaels Sweeping Chesapeake Bay views with Sandy Beach,dock, pool.

  • 4 BR/3 BA House (sleeps 8)
    $1,913 - $3,998/wk
    per house, dock boatslip, DVD, fireplace, grill, linens provided, pets, private pool, Fully Equipped Kitchen

St. Michaels 90 acre farm with wrap around views, 5 minutes to St. Michaels, pool, dock

  • 4 BR/2 BA House (sleeps 8)
    $1,453 - $3,325/wk
    per house, dock boatslip, DVD, fireplace, grill, pets, private pool, Fully Equipped Kitchen, Linens with Fee

Port Republic Magical Bayfront Home

  • 3 BR/2 BA House (sleeps 8)
    $300 - $350/nt
    $1,800 - $2,500/wk
    per property, beach, waterfront, pets considered, air-conditioning, internet access, satellite or cable, TV, DVD, barbecue

Port Republic Treasure the Chesapeake Bay w/Beachfront Home

  • 3 BR/2 BA House (sleeps 7)
    $1,200 - $1,600/wk
    per property, beach, waterfront, pool, tennis court, air-conditioning, TV, DVD, parking, fireplace

St. Michaels Charming Cozy Cove Cottage Romatic Getaway or Family Retreat

  • 3 BR/1 BA Cottage (sleeps 6)
    $1,025/wk
    per property, garden, air-conditioning, satellite or cable, TV, DVD, parking

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

  • 3 BR/2 BA Lodge (sleeps 8)
    $250 - $275/nt
    $1,450 - $1,650/wk
    per property, beach, town, garden, pets considered, air-conditioning, internet access, satellite or cable, TV, DVD

Tilghman Island 'Knapp Shack'- Brand new waterfront townhome overlooking the Bay

  • 3 BR/2 BA, 1 half bath House (sleeps 6)
    $225 - $300/nt
    $1,250 - $1,750/wk
    per property, waterfront, balcony, pets considered, air-conditioning, internet access, satellite or cable, TV, DVD

Chestertown Cozy up by the Big Stone Fireplace For the Holidays and Enjoy the Waterviews

  • 6 BR/6 BA House (sleeps 12)
    $495 - $895/nt
    $2,695 - $5,495/wk
    per property, rural, waterfront, garden, balcony, air-conditioning, satellite or cable, TV, DVD, parking

Deal Island Chesapeake Sunrise~Sunset Cottage (Fantastic Bay views) Fall Weeek end $255

  • 3 BR/2 BA House (sleeps 8)
    $80 - $95/nt
    $625/wk
    per property, village, waterfront, garden, balcony, air-conditioning, internet access, satellite or cable, TV, DVD
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Point Lookout Luxury Chesapeake Bay Waterfront - Enjoy Miles of Sandy Beach

  • 4 BR/3 BA House (sleeps 12)
    $1,500/wk
    $4,000/month
    per property, beach, balcony, air-conditioning, internet access, satellite or cable, TV, DVD, parking

St. Michaels Expansive 5BR home with great wide water views, pool, beautifully decorated

  • 5 BR/3 BA House (sleeps 10)
    $2,873 - $6,462/wk
    per house, dock boatslip, DVD, fireplace, grill, linens provided, pets not allowed, private pool, Fully Equipped Kitchen

St. Michaels Away from it all! Secluded spot for rest and relaxation, pool, dock, great kayaking!

  • 3 BR/2 BA Cottage (sleeps 6)
    $1,291 - $2,696/wk
    per cottage, dock boatslip, DVD, grill, linens provided, pets, private pool, Fully Equipped Kitchen

Easton Fantastic restored barn with expansive waterviews, pool, deep water dock

  • 4 BR/3 BA House (sleeps 8)
    $4,149 - $5,649/wk
    per house, dock boatslip, DVD, fireplace, grill, linens provided, pets not allowed, private pool, Fully Equipped Kitchen

Cobb Island Enjoy Best Southern Maryland Waterfront Home - with Private Beach and Dock

  • 4 BR/2 BA House (sleeps 10)
    $350 - $375/nt
    $1,500 - $2,350/wk
    per property, river, waterfront, air-conditioning, internet access, satellite or cable, TV, DVD, parking, barbecue

St. Michaels Authentic 1920's Waterman's Cottage

  • 2 BR/1 BA Cottage (sleeps 4)
    $1,090 - $1,490/wk
    per cottage, dock boatslip, DVD, fireplace, grill, pets, Fully Equipped Kitchen, Linens with Fee

Tilghman Island Tilghman Island Victorian - The Jackson House c1890

  • 3 BR/2 BA, 1 half bath House (sleeps 6)
    $175/nt
    $900/wk
    per property, near the ocean, town, pool, garden, pets considered, air-conditioning, internet access, satellite or cable, TV

North East Top of the Chesapeake - Minutes from Historic Charlestown

  • 5 BR/2 BA House (sleeps 11)
    $300 - $420/nt
    $2,090 - $2,250/wk
    $3,900 - $4,450/month
    per property, river, waterfront, balcony, pets considered, air-conditioning, internet access, satellite or cable, TV, DVD

St. Michaels Fresh & Brand New: - 3 night fall special! Also free sailing adventure!

  • 3 BR/2 BA, 1 half bath House (sleeps 8)
    $1,500 - $2,680/wk
    per property, resort, town, pool, pets considered, air-conditioning, satellite or cable, TV, DVD, parking

St. Michaels Best View in the Area of Eastern Bay! Pool, Canoe, game room on 56 acres!

  • 4 BR/4 BA, 1 half bath Estate (sleeps 8)
    $4,750/wk
    per property, waterfront, pool, garden, balcony, internet access, satellite or cable, TV, DVD
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