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Chesapeake Bay Pet Friendly Cottage Rentals(52)

52 Results
$257 - $400
per night
2 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
2 - 7 night min stay
(35)
$2,132 - $2,518
per week
7 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
(34)
$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 5
7 night min stay
2 Reviews
$2,686 - $3,265
per week
7 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
7 night min stay
(19)
  • 7 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 14
7 night min stay
(3)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
7 night min stay
(3)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night min stay
(3)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
1 Review
  • 2 BR,
  • 2 BA,
  • Sleeps 6
(5)
$200 - $250
per night
2 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 7
2 night min stay
$125 - $175
per night
2 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 night min stay
(3)
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
7 night min stay
(63)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 7
(9)
  • 2 BR,
  • 1 BA,
  • Sleeps 5
2 - 5 night min stay
(12)
  • 1 BR,
  • 1 BA,
  • Sleeps 3
1 - 4 night min stay
(18)
$159 - $260
per night
3 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night min stay
(26)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night min stay
(12)
$195 - $275
per night
2 - 3 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
2 - 3 night min stay
(3)
$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
(9)
  • 3 BR,
  • 2 BA,
  • Sleeps 9
3 night min stay
(5)
$2,240 - $3,708
per week
7 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
(4)
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
7 night min stay
(4)
$200 - $250
per night
2 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 7
2 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 night min stay
(3)
26 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
(14)
$120 - $160
per night
2 - 4 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 3
2 - 4 night min stay
(22)
  • 4 BR,
  • 3 BA,
  • Sleeps 10
1 - 7 night min stay
(9)
 

Recent Chesapeake Bay Reviews

Wonderful Experience

5 of 5
My guy, myself and our pup spend three nights here in early April and I wish it could have been thirty more. The cottage is smallish, but so cozy, clean and well put together. Really absolutely perfect for a couple. The island itself is so relaxing and naturally gorgeous that we have already started making plans to return and we've not even been home a week. Mo's home is wonderful with all the conveniences (and so many movie/sports channels for those who watch) :), the island is rustic and so relaxing. Thank you for a wonderful trip. We will be back.
  • Submitted: Apr 8, 2015
  • Stayed: Apr 2015

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

Very nice . . .

5 of 5
Our stay at the cottage was not long enough. The tasteful decorations, supplies on hand combined with the beautiful weather made our first trip to this area a memorable one. Our dog had a fantastic time playing in the water, running the beach and trying to catch sea creatures. The deck off the side was just right for coffee, cocktails and talking. The overall peace and tranquility of the area was amazing. We are looking forward to returning next year. Thank you for helping us celebrate our trip.
  • Submitted: Oct 3, 2014
  • Stayed: Sep 2014