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Chesapeake Bay Cottage Rentals with pool(21)

21 Results
$250 - $400
per night
2 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
2 - 7 night minimum stay
(35)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
(8)
$625 - $729
per night
2 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 9
2 - 7 night minimum stay
(5)
$85 - $90
per night
2 night minimum stay
  • 1 BR,
  • 1 HF BA,
  • Sleeps 2
2 night minimum stay
2 Reviews
$100 - $175
per night
2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 night minimum stay
(3)
$2,686 - $3,265
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
7 night minimum stay
(19)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(4)
$3,116 - $5,305
per week
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
7 night minimum stay
(4)
$2,099 - $3,373
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
1 Review
$120 - $160
per night
2 - 4 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 3
2 - 4 night minimum stay
(22)
$135 - $180
per night
3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
3 night minimum stay
(33)
$150 - $225
per night
2 - 5 night minimum stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
2 - 5 night minimum stay
(4)
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 5
2 - 7 night minimum stay
(13)
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 5
2 - 3 night minimum stay
(9)
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 night minimum stay
(3)
$2,446 - $3,991
per week
7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(30)
$2,441 - $3,909
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 7
7 night minimum stay
(43)
  • 1 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
(16)
$225 - $350
per night
3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(13)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
(7)
  • 3 BR,
  • Sleeps 8
2 night minimum stay
 

Recent Chesapeake Bay Reviews

Perfect cottage for a girls weekend

5 of 5
Harbor Hideaway was the PERFECT cottage for our girls getaway. This was our first time to St. Michaels, and we're already planning next years trip (and stay in Harbor Hideaway, of course). The cottage had everything we needed, and we really appreciated all of the owner's little touches to make it feel like home. Everything was so clean and cozy! The location is perfect, too - we walked to all of the shops and restaurants in town. There was snow on the ground so we didn't get to appreciate the backyard, but it looked perfect and spacious. And, I can't say enough about how easy it was to work with Carol, the owner. I'd definitely recommend this place to anyone! Can't wait until next year!
  • Submitted: Mar 10, 2015
  • Stayed: Mar 2015

Romantic Anniversary!

5 of 5
This bungalow was the perfect spot for our 25th wedding anniversary! Everything we wanted - private, romantic, beautiful property all around us and the cove at our doorsteps! We kayaked right off the pier. The owner and her family were great! Absolutely no complaints and will be back next summer!
  • Submitted: Aug 26, 2012
  • Stayed: Aug 2012