Self-catering holiday homes in Chesapeake Bay

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

  1. Maryland,
  2. Chesapeake Bay,
  3. Chestertown Vacation rentals
— Property 254204
Chesapeake Bay house rental - Waterveiw side of house
6 Bedrooms, Sleeps 12,
House, 6 Bathrooms, rural, waterfront, garden
Rates - per property (GBP)
£302 - £546/night
£1,643 - £3,351/week
Calendar Updated 13 Nov 2009
Contact the Owner
Details and Availability
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Fantastic Family Compound 1/2 mile to St. Michaels, Pool, Dock, Hot tub

  1. Maryland,
  2. Chesapeake Bay,
  3. St. Michaels Vacation rentals
— Property 7004796h
5 Bedrooms/4 Bathrooms House (Sleeps 10 boat dock, DVD, fireplace, grill, indoor hot tub, linen provided, pool table, pets not allowed, starting at £1,731/week
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Chesapeake Bay Waterfront Luxury Vacation Home Near Solomon's Island

  1. Maryland,
  2. Chesapeake Bay,
  3. St. Leonard Vacation rentals
— Property 122821
3 Bedrooms/3 Bathrooms House (Sleeps 10 beach, waterfront, pets considered, air-conditioning, satellite or cable, TV, DVD, fireplace, starting at £183/night £945/week
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Beautifully appointed vacation home outside St. Michaels

  1. Maryland,
  2. Chesapeake Bay,
  3. St. Michaels Vacation rentals
— Property 7022556h
6 Bedrooms/5 Bathrooms House (Sleeps 12 boat dock, DVD, fireplace, grill, linen provided, pool table, pets not allowed, private pool, starting at £1,982/week
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Lighthouse Replica Home Right on the Water

  1. Maryland,
  2. Chesapeake Bay,
  3. North East Vacation rentals
— Property 154370
4 Bedrooms/4 Bathrooms House (Sleeps 8 beach, waterfront, jacuzzi, air-conditioning, satellite or cable, TV, DVD, parking, fireplace
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Budget friendly cottage getaway, with rowboat included!

  1. Maryland,
  2. Chesapeake Bay,
  3. St. Michaels Vacation rentals
— Property 7022552h
4 Bedrooms/2 Bathrooms Cottage (Sleeps 8 boat dock, DVD, fireplace, grill, pets, Fully Equipped Kitchen, Linens with Fee, starting at £802/week
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Waterfront Home with Private Dock

  1. Maryland,
  2. Chesapeake Bay,
  3. St. Michaels Vacation rentals
— Property 123352
4 Bedrooms/2 Bathrooms, 1 Separate Toilet House (Sleeps 8 river, waterfront, communal pool, garden, balcony, pets considered, air-conditioning, satellite or cable, TV, starting at £146/night £732/week
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Charming Tilghman Island getaway cottage

  1. Maryland,
  2. Chesapeake Bay,
  3. Tilghman Island Vacation rentals
— Property 7007441h
4 Bedrooms/2 Bathrooms Cottage (Sleeps 8 DVD, fireplace, grill, indoor hot tub, pets, Fully Equipped Kitchen, Linens with Fee, starting at £646/week
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Cottage with pool, hot tub and great water

  1. Maryland,
  2. Chesapeake Bay,
  3. St. Michaels Vacation rentals
— Property 7018652h
4 Bedrooms/4 Bathrooms House (Sleeps 8 boat dock, DVD, grill, indoor hot tub, linen provided, pets not allowed, private pool, Fully Equipped Kitchen, starting at £1,039/week
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Light Filled Contemporary with 4 Queen bedrooms, dock,pool

  1. Maryland,
  2. Chesapeake Bay,
  3. St. Michaels Vacation rentals
— Property 7004815h
4 Bedrooms/2 Bathrooms House (Sleeps 9 boat dock, DVD, fireplace, grill, linen provided, pets, private pool, Fully Equipped Kitchen, starting at £1,065/week
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Expansive 4 bedroom home 5 blocks to town of St. Michaels, wide water views.

  1. Maryland,
  2. Chesapeake Bay,
  3. St. Michaels Vacation rentals
— Property 7004814h
4 Bedrooms/3 Bathrooms House (Sleeps 8 boat dock, DVD, fireplace, grill, pets, Fully Equipped Kitchen, Linens with Fee, starting at £771/week
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Fun house outside St. Michaels, pool, dock, hot tub, ping pong

  1. Maryland,
  2. Chesapeake Bay,
  3. St. Michaels Vacation rentals
— Property 7007440h
4 Bedrooms/3 Bathrooms House (Sleeps 8 boat dock, DVD, fireplace, grill, indoor hot tub, pets, private pool, Fully Equipped Kitchen, starting at £898/week
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4BR waterfront home outside Chestertown, wide water views!

  1. Maryland,
  2. Chesapeake Bay,
  3. Chestertown Vacation rentals
— Property 7004812h
4 Bedrooms/3 Bathrooms House (Sleeps 8 DVD, fireplace, grill, linen provided, pool table, pets not allowed, Fully Equipped Kitchen, starting at £764/week
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Very private 25 acre home with sunset views, deep water dock, pool

  1. Maryland,
  2. Chesapeake Bay,
  3. St. Michaels Vacation rentals
— Property 7004811h
4 Bedrooms/3 Bathrooms House (Sleeps 8 boat dock, DVD, fireplace, grill, pets, private pool, Fully Equipped Kitchen, Linens with Fee, starting at £1,008/week
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Contemporary Cottage with pool, tranquil views and great nature watching!

  1. Maryland,
  2. Chesapeake Bay,
  3. St. Michaels Vacation rentals
— Property 7014511h
3 Bedrooms/2 Bathrooms Cottage (Sleeps 8 boat dock, DVD, fireplace, grill, linen provided, pets, private pool, Fully Equipped Kitchen, starting at £1,004/week
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Waterfront Cottage minutes to St. Michaels, hot tub

  1. Maryland,
  2. Chesapeake Bay,
  3. St. Michaels Vacation rentals
— Property 7018650h
3 Bedrooms/2 Bathrooms Cottage (Sleeps 5 DVD, fireplace, grill, indoor hot tub, linen provided, pets not allowed, Fully Equipped Kitchen, starting at £828/week
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Conveniently located home between Easton and St. Michaels, private with Tred Avon views!

  1. Maryland,
  2. Chesapeake Bay,
  3. St. Michaels Vacation rentals
— Property 7015502h
3 Bedrooms/2 Bathrooms Cottage (Sleeps 6 boat dock, DVD, fireplace, grill, linen provided, pets not allowed, Fully Equipped Kitchen, starting at £838/week
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Single family getaway! Pool, playgym, dock, and more!

  1. Maryland,
  2. Chesapeake Bay,
  3. St. Michaels Vacation rentals
— Property 7004805h
3 Bedrooms/1 Bathroom Cottage (Sleeps 6 boat dock, DVD, fireplace, grill, pets, private pool, Fully Equipped Kitchen, starting at £810/week
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Bungalow in heart of historic district

  1. Maryland,
  2. Chesapeake Bay,
  3. St. Michaels Vacation rentals
— Property 7004802h
2 Bedrooms/2 Bathrooms Cottage (Sleeps 4 DVD, grill, pets, Fully Equipped Kitchen, Linens with Fee, starting at £701/week
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Historic Estate with 5BR's, pool, hot tub, gourmet kitchen and deep water dock.

  1. Maryland,
  2. Chesapeake Bay,
  3. St. Michaels Vacation rentals
— Property 7004801h
5 Bedrooms/4 Bathrooms House (Sleeps 14 boat dock, DVD, fireplace, grill, indoor hot tub, linen provided, pets, private pool, starting at £1,587/week
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Tilghman Island Cottage with pool, dock, hot tub and wide views!

  1. Maryland,
  2. Chesapeake Bay,
  3. Tilghman Island Vacation rentals
— Property 7018649h
3 Bedrooms/3 Bathrooms Cottage (Sleeps 7 boat dock, DVD, grill, indoor hot tub, linen provided, pets, private pool, Fully Equipped Kitchen, starting at £825/week
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Tilghman Island getaway with private dock, great views, and more!

  1. Maryland,
  2. Chesapeake Bay,
  3. Tilghman Island Vacation rentals
— Property 7007436h
3 Bedrooms/2 Bathrooms Cottage (Sleeps 6 boat dock, DVD, grill, pets, Fully Equipped Kitchen, starting at £957/week
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Sweeping Chesapeake Bay views with Sandy Beach,dock, pool.

  1. Maryland,
  2. Chesapeake Bay,
  3. St. Michaels Vacation rentals
— Property 7004795h
4 Bedrooms/3 Bathrooms House (Sleeps 8 boat dock, DVD, fireplace, grill, linen provided, pets, private pool, Fully Equipped Kitchen, starting at £1,166/week
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90 acre farm with wrap around views, 5 minutes to St. Michaels, pool, dock

  1. Maryland,
  2. Chesapeake Bay,
  3. St. Michaels Vacation rentals
— Property 7004794h
4 Bedrooms/2 Bathrooms House (Sleeps 8 boat dock, DVD, fireplace, grill, pets, private pool, Fully Equipped Kitchen, Linens with Fee, starting at £886/week
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Magical Bayfront Home

  1. Maryland,
  2. Chesapeake Bay,
  3. Port Republic Vacation rentals
— Property 212770
3 Bedrooms/2 Bathrooms House (Sleeps 8 beach, waterfront, pets considered, air-conditioning, internet access, satellite or cable, TV, DVD, barbecue, starting at £183/night £1,098/week £4,390/month
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Treasure the Chesapeake Bay w/Beachfront Home

  1. Maryland,
  2. Chesapeake Bay,
  3. Port Republic Vacation rentals
— Property 227213
3 Bedrooms/2 Bathrooms House (Sleeps 7 beach, waterfront, communal pool, tennis court, air-conditioning, TV, DVD, parking, fireplace, starting at £732/week
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Cove Point Beach House at Chesapeake Bay near Solomons Island, MD

  1. Maryland,
  2. Chesapeake Bay,
  3. Solomons Island Vacation rentals
— Property 238892
3 Bedrooms/1 Bathroom, 1 Separate Toilet House (Sleeps 6 beach, near the sea, air-conditioning, internet access, satellite or cable, TV, DVD, starting at £61/night £482/week
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Adorable and Cozy Cape with wide water views, minutes to St. Michaels

  1. Maryland,
  2. Chesapeake Bay,
  3. St. Michaels Vacation rentals
— Property 7004820h
3 Bedrooms/3 Bathrooms Cottage (Sleeps 7 boat dock, DVD, fireplace, grill, linen provided, pets not allowed, Fully Equipped Kitchen, starting at £823/week
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One level vacation home outside St. Michaels, pool, wide views, great breezes

  1. Maryland,
  2. Chesapeake Bay,
  3. St. Michaels Vacation rentals
— Property 7007442h
3 Bedrooms/3 Bathrooms House (Sleeps 8 DVD, fireplace, grill, linen provided, pets, private pool, Fully Equipped Kitchen, starting at £1,063/week
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Upscale home outside St. Michaels, pool, dock, newly renovated kitchen and baths, a fabulous retreat

  1. Maryland,
  2. Chesapeake Bay,
  3. St. Michaels Vacation rentals
— Property 7004819h
6 Bedrooms/3 Bathrooms House (Sleeps 11 boat dock, DVD, fireplace, grill, linen provided, pets, private pool, Fully Equipped Kitchen, starting at £1,738/week
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