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Chesapeake Bay Short Term Vacation Rentals(115)

115 Results
  • 4 BR,
  • 2 BA,
  • Sleeps 9
3 - 7 night min stay
(26)
  • 12 BR,
  • 8 BA,
  • 1 HF BA,
  • Sleeps 40
2 - 7 night min stay
(11)
  • 4 BR,
  • 4 BA,
  • Sleeps 8
3 - 7 night min stay
(35)
  • 6 BR,
  • 6 BA,
  • Sleeps 15
2 - 7 night min stay
(19)
$525 - $690
per night
3 - 5 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 16
3 - 5 night min stay
(9)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 night min stay
(4)
$825 - $985
per night
2 night min stay
  • 6 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 14
2 night min stay
1 Review
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night min stay
(3)
  • 1 BR,
  • 1 HF BA,
  • Sleeps 2
2 night min stay
2 Reviews
$899
per night
3 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 10
3 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
2 - 7 night min stay
(19)
  • 5 BR,
  • 5 BA,
  • Sleeps 10
3 night min stay
(5)
  • 4 BR,
  • 3 BA,
  • Sleeps 12
3 night min stay
2 Reviews
$650 - $700
per night
3 - 7 night min stay
  • 7 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 18
3 - 7 night min stay
(7)
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 12
2 - 4 night min stay
1 Review
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 19
2 - 7 night min stay
  • 3 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 4 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 10
2 - 7 night min stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
2 night min stay
$250 - $300
per night
2 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 10
2 night min stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
  • 5 BR,
  • 2 BA,
  • Sleeps 10
2 - 7 night min stay
1 Review
$125 - $175
per night
2 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 night min stay
(3)
$209 - $349
per night
3 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
3 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 9
2 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 night min stay
(6)
$200 - $250
per night
2 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 7
2 night min stay
$250
per night
2 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 3
2 night min stay
$899 - $1,199
per night
1 - 3 night min stay
  • 3 BR,
  • 4 BA,
  • Sleeps 10
1 - 3 night min stay
 

Recent Chesapeake Bay Reviews

What a peaceful and beautiful space to spend time!

5 of 5
I had a wonderfully relaxing visit to Watermark with my family. We loved the house and property--the house is so spacious and is beautifully appointed. We loved that each of us had plenty of space to ourselves--the bedrooms are large and have comfortable places to sit and read, and the common spaces are beautifully appointed and enormous so even with a big group one doesn't feel packed in. It is the perfect house for a family vacation! The property is beautiful and being able to walk down to the private beach and dock was a huge treat. Sunsets from the house or the dock are not to be missed! We can't wait to go back to Watermark.
  • Submitted: Apr 1, 2015
  • Stayed: Mar 2015

Shhhhh! This place is a blissfully secluded gem.

5 of 5
The owner was very responsive and helpful. The place was well maintained and clean. It was nice having the beds made on arrival. The lawn was great for games. The beach was pleasant and we all enjoyed looking for the plentiful sea glass!
  • Submitted: Aug 28, 2014
  • Stayed: Aug 2014

A COMFORTABLE STEP BACK IN TIME

5 of 5
Upon arrival we saw Geaorge and Jackie waiting for us in the rockers on the front porch. They greeted us warmly and showed us arouond the house and immediate property, too much property to cover it all! They assured us that we could call them day or night if the need arose and even showed up one day with fresh tomatoes from their garden, and graciously gave us the Historical tour of the Windmill and other items of historical interest on the property. This lovely property is right on the water and has many trails to follow, one even leads to an Indian burial mound and Eagles nest. It all was very well maintained inside and out. We numbered 15 and all found it a very interesting and fun place to spend our time together, I would recommend this rental to anyone and, in fact, already have.
  • Submitted: Aug 17, 2014
  • Stayed: Aug 2014