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185 Results
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185 Results
$350
per night
2 - 3 night min stay
  • 6 BR,
  • 3 BA,
  • Sleeps 14
2 - 3 night min stay
(4)
  • 5 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 7 night min stay
2 Reviews
  • 6 BR,
  • 2 BA,
  • Sleeps 11
2 night min stay
(10)
  • 3 BR,
  • 2 BA,
  • Sleeps 9
2 night min stay
$750
per night
3 night min stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 13
3 night min stay
2 Reviews
$1,400
per week
7 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 10
7 night min stay
1 Review
  • 4 BR,
  • 1 BA,
  • Sleeps 8
2 - 7 night min stay
(8)
  • 6 BR,
  • 5 BA,
  • Sleeps 20
2 - 7 night min stay
(18)
$243 - $350
per night
3 - 7 night min stay
  • 3 BR,
  • 1 BA,
  • Sleeps 6
3 - 7 night min stay
(7)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 7 night min stay
2 Reviews
  • 5 BR,
  • 4 BA,
  • Sleeps 10
7 night min stay
2 Reviews
$899
per night
3 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 10
3 night min stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
3 night min stay
1 Review
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night min stay
(3)
  • 4 BR,
  • 5 BA,
  • Sleeps 10
3 - 7 night min stay
$795 - $995
per night
2 night min stay
  • 5 BR,
  • 4 BA,
  • Sleeps 10
2 night min stay
$1,379 - $1,500
per night
3 - 7 night min stay
  • 6 BR,
  • 5 BA,
  • Sleeps 12
3 - 7 night min stay
  • 4 BR,
  • 4 BA,
  • Sleeps 8
2 night min stay
2 Reviews
$795 - $995
per night
2 night min stay
  • 5 BR,
  • 4 BA,
  • Sleeps 10
2 night min stay
$1,351
per week
7 night min stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
7 night min stay
(13)
  • 6 BR,
  • 3 BA,
  • Sleeps 12
(3)
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 13
(7)
$5,000
per month
90 night min stay
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 8
90 night min stay
$350
per night
2 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
2 night min stay
(8)
  • 2 BR,
  • 1 BA,
  • Sleeps 6
3 night min stay
2 Reviews
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 17
(12)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
5 - 7 night min stay
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 6 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
7 night min stay
(5)
$200 - $343
per night
3 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night min stay
(4)
 

Recent Chesapeake Bay Reviews

Chesapeake Beach comfort with amazing view

5 of 5
what a great place! Everything you could need and a great view with it. The house was just renovated and it has everything you could need. The decks are great and more chairs then you will ever need. Great sound system that pumps music outside. A 5 minute drive to Herrington harbor south for fishing. Response times to any questions was immediate. I highly recommend staying here, unless it's the times when I want it!
  • Submitted: May 4, 2015
  • Stayed: Apr 2015

Loved It!

5 of 5
My husband and I stayed at this property in 2013 and 2014, both times to celebrate our wedding anniversary. We love the architecture and the design of the home. 2013 was our first time to St. Michaels and we fell in love with the town, as well. It's a beautiful home and incredibly peaceful. It's hard not to fall in love with so much beauty and serenity all around you. And, St. Michaels has lots of shops, restaurants and areas of interest to visit. The property manager, Angela, provided lots of insight and ideas about things to do and ways to enjoy St. Michaels while also being available if we needed to contact her. We hope to visit again and would highly recommend it to others.
  • Submitted: Feb 16, 2015
  • Stayed: May 2014

Beautiful property with wonderful location

5 of 5
2014 was our 5th year at this amazing house. It has eveything you could want for a vacation and our family really enjoy staying here. The listing description is accurate so too is all the other information about the property. The location is serene and beautiful and the house is stunning, the pool is loved by us all and the surrounding area is very interesting. We have just booked for our 6th year and can't wait to return. We are more than happy to recommend this property to any prospective renters.
  • Submitted: Dec 30, 2014
  • Stayed: Jul 2014