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Chesapeake Bay Vacation Rentals with pool(139)

139 Results
  • 4 BR,
  • 4 BA,
  • Sleeps 8
3 - 7 night min stay
(36)
  • 6 BR,
  • 6 BA,
  • Sleeps 15
2 - 7 night min stay
(20)
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 4 night min stay
(39)
  • 5 BR,
  • 4 BA,
  • Sleeps 10
2 - 7 night min stay
(16)
$795 - $1,362
per night
3 - 7 night min stay
  • 5 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 7 night min stay
(17)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night min stay
(3)
$450 - $700
per night
2 night min stay
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
2 night min stay
(11)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night min stay
(72)
$1,050 - $1,250
per night
2 - 3 night min stay
  • 7 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 20
2 - 3 night min stay
(12)
$750 - $850
per night
2 - 3 night min stay
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 12
2 - 3 night min stay
(6)
$1,143 - $8,000
per night
3 - 7 night min stay
  • 7 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 28
3 - 7 night min stay
(9)
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 15
3 night min stay
(8)
$700 - $2,000
per night
2 - 7 night min stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 18
2 - 7 night min stay
(10)
$6,500
per week
7 night min stay
  • 4 BR,
  • 4 BA,
  • Sleeps 8
7 night min stay
(6)
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 20
2 - 7 night min stay
(4)
  • 6 BR,
  • 6 BA,
  • Sleeps 14
3 - 7 night min stay
(8)
  • 14 BR,
  • 6 BA,
  • 2 HF BA,
  • Sleeps 50
2 - 7 night min stay
(3)
$257 - $400
per night
2 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
2 - 7 night min stay
(35)
$625 - $729
per night
2 - 7 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 9
2 - 7 night min stay
(5)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 night min stay
2 Reviews
  • 5 BR,
  • 6 BA,
  • 2 HF BA,
  • Sleeps 10
2 night min stay
(5)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
(8)
$425 - $750
per night
2 night min stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night min stay
$786 - $800
per night
3 - 7 night min stay
  • 6 BR,
  • 4 BA,
  • Sleeps 12
3 - 7 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
(6)
  • 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 18
2 - 7 night min stay
  • 3 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 4 night min stay
 

Recent Chesapeake Bay Reviews

Beautiful view right on the water

5 of 5
We rented this property for the weekend and it was perfect for 7 couples. With a breathtaking view right on the water, we were outside all day, enjoying the beautiful summer day grilling and swimming in the pool. The accommodations were great and the house provided everything we needed to have a perfect weekend.
  • Submitted: May 20, 2015
  • Stayed: May 2015

Unexpected relaxation and privacy.

5 of 5
When I headed toward St. Michael's with my family I expected a reasonably nice vacation house in a pretty populated area. Instead we were treated to a very cool, spacious house on a 6 acres of private land. The house has very good soothing energy. My kid could not run away where I would not see him. It was a bit chilly for the pool, but I would be a blast in the summer. If you are not up to all the fine dining places in nearby town, the fully equipped new clean kitchen is there for you.Camfire with s'mores and spooky stories at night was the highlight of the day for the kids. The beach is very small and private. If you want to play beach volleyball you may want to drive to a public beach, but for sunbathing and water is it just perfect. This is one of rare places where I could rejuvenate in 3 days while vacationing with the whole family. We will definitely be back! Thank you, owners for thinking of your guests while renovating this house!
  • Submitted: May 14, 2015
  • Stayed: May 2015

Magnificent!

5 of 5
Beautiful, well-mainained, nicely appointed home. We enjoyed our stay and the layout and amenities were exactly as described. Large bedrooms and kitchen, and lots of spaces for spending time with family. The property is perfectly located, and the views are amazing! The house had everything we needed - and more! We hope to visit again and had a wonderful experience with the owner.
  • Submitted: May 6, 2015
  • Stayed: May 2015