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Chesapeake Bay Cottage Rentals(48)

48 Results
$350 - $450
per night
2 - 3 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 3 night min stay
(9)
$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 8
(8)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
(4)
$250
per night
2 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 3
2 night min stay
$200 - $250
per night
2 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 7
2 night min stay
$100 - $175
per night
2 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 night min stay
(3)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 7
(9)
$330 - $495
per night
2 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
2 night min stay
(7)
  • 2 BR,
  • 1 BA,
  • Sleeps 5
3 night min stay
(12)
  • 1 BR,
  • 1 BA,
  • Sleeps 3
1 - 4 night min stay
(18)
$137 - $260
per night
3 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night min stay
(25)
$250 - $350
per night
2 night min stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night min stay
(5)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night min stay
(12)
$107 - $110
per night
3 - 7 night min stay
  • 3 BR,
  • 1 BA,
  • Sleeps 6
3 - 7 night min stay
(10)
  • 3 BR,
  • 1 BA,
  • Sleeps 5
2 - 5 night min stay
(29)
$300
per night
2 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 night min stay
(7)
$115 - $135
per night
3 - 5 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
3 - 5 night min stay
(8)
  • 3 BR,
  • 2 BA,
  • Sleeps 9
3 night min stay
(5)
$200 - $250
per night
2 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 7
2 night min stay
$200
per night
2 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 night min stay
  • 3 BR,
  • 1 BA,
  • Sleeps 6
(4)
25 more choices from the HomeAway Network
$225 - $428
per night
2 - 6 night min stay
  • 4 BR,
  • 4 BA,
  • Sleeps 10
2 - 6 night min stay
(22)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 night min stay
(13)
$120 - $160
per night
2 - 4 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 3
2 - 4 night min stay
(22)
$135 - $180
per night
3 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
3 night min stay
(33)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
3 night min stay
(12)
  • 4 BR,
  • 3 BA,
  • Sleeps 10
1 - 7 night min stay
(9)
$300
per night
3 night min stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
3 night min stay
(9)
 

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

Great place to relax

5 of 5
The Cottage has been our vacation get-away for the last 3 years and we are planning to return again this year. Our children (one in college and one in high school) love it there. If you enjoy peace and quiet, like to fish and crab and like to have some elbow room to roam, this is the place for you! There are only about 8 houses on the cove and rarely did we even see a boat. You don’t need a boat to enjoy the water there is a nice pier and the area is great for canoeing. The cottage is located away from traffic which makes it perfect for running and biking. Cambridge is only 10 minutes away and easy to get to so if you forget anything it’s an easy trip to pick it up.
  • Submitted: Jan 3, 2015
  • Stayed: Jul 2014

Great fall weekend

5 of 5
My wife and I and a few friends spent a 3 day weekend in October at the cottage. The water view was great and we enjoyed using the fishing pier. About half the time we were there it was rainy, but spending time inside was enjoyable withe the "Florida room," giving us a nice view and the open kitchen/living room. We brought our dog as well and that worked out nicely.
  • Submitted: Oct 25, 2014
  • Stayed: Oct 2014