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Chesapeake Bay Waterfront Cottage Rentals(44)

44 Results
$434 - $515
per night
2 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
2 - 3 night minimum stay
(63)
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 3 night minimum stay
(27)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 night minimum stay
(9)
$439 - $632
per night
2 - 3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 3 night minimum stay
(34)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
3 night minimum stay
(27)
  • 3 BR,
  • 2 BA,
  • Sleeps 9
7 night minimum stay
(5)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
(7)
$505 - $663
per night
2 - 3 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 7
2 - 3 night minimum stay
(43)
$506 - $594
per night
2 - 3 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 3 night minimum stay
(30)
$100 - $175
per night
1 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
1 - 3 night minimum stay
2 Reviews
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 7
2 night minimum stay
(8)
  • 2 BR,
  • 1 BA,
  • Sleeps 5
3 night minimum stay
(12)
$280 - $495
per night
2 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
2 night minimum stay
(7)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
2 - 3 night minimum stay
(20)
$137 - $260
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(24)
$150 - $193
per night
3 - 7 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 6
3 - 7 night minimum stay
2 Reviews
$85 - $90
per night
2 night minimum stay
  • 1 BR,
  • 1 HF BA,
  • Sleeps 2
2 night minimum stay
2 Reviews
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 3 night minimum stay
(8)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 - 7 night minimum stay
(3)
  • 3 BR,
  • 1 BA,
  • Sleeps 5
2 - 5 night minimum stay
(27)
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 - 7 night minimum stay
  • 2 BR,
  • Sleeps 4
2 night minimum stay
1 Review
$115 - $125
per night
3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
3 night minimum stay
(7)
  • 3 BR,
  • 1 BA,
  • Sleeps 6
(4)
$300
per night
2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 night minimum stay
(7)
19 more choices from the HomeAway Network
  • 3 BR,
  • 1 BA,
  • Sleeps 6
2 - 3 night minimum stay
(16)
$770
per week
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 8
7 night minimum stay
(9)
$135 - $180
per night
3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
3 night minimum stay
(32)
$300 - $342
per night
3 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
3 night minimum stay
(9)
  • 3 BR,
  • 1 BA,
  • Sleeps 6
2 night minimum stay
(14)
 

Recent Chesapeake Bay Reviews

Perfect weekend away

5 of 5
We spent a long weekend in this great cottage by the bay and couldn't have been happier. It was 5 of us and the property was wonderful. The pictures really don't do it justice! In addition to being a great home, it is immaculately clean and well appointed. I would highly recommend this property for a getaway on the Eastern Shore.
  • Submitted: Aug 20, 2014
  • Stayed: Aug 2014

Look No Further!!!

5 of 5
Wow!!! If you're looking for a clean, comfortable, relaxing vacation cottage, look no further! This was one of the most relaxing vacations we've ever had! We spent each morning on the wrap-around porch with our coffee watching the sun come up over the water. The only sounds were the fish jumping and the birds singing. We wanted to try our hand at crabbing and were not disappointed! Bob and Joan not only provided everything you could need in the cottage but also had everything needed for crabbing. Even the bait! If you're looking for a fun daytrip, the Boardwalk at Ocean City was an easy, short drive. The beach there was so clean and beautiful! Although, one day away from this "piece of Heaven" was enough for us. So.. grab your fishing gear, a good book, and great company and head to this beautifully kept property! You won't be disappointed! Thank you Bob and Joan for sharing this property with us! We will definitely be back!
  • Submitted: Aug 17, 2014
  • Stayed: Aug 2014

Awesome time

5 of 5
I spent 10 days in Deal Island's cottage and wished I could have stayed another 10. The cottage was clean and quaint and had everything I needed, I particularly enjoyed the screen porch where a breeze from the bay could be felt almost anytime. I was worried at first that the cottage would be too hot to sleep at night but the window ac was more than enough And I had to shut it off as it became too cold. Mo the owner and all the locals I met were welcoming and friendly and the island was quiet without all the beach traffic and tourist traps, just what I was looking for. My dogs had a great time walking and sleeping on the little beach where we spent much of our time since the weather was great, I read, ate and relaxed. Hopefully I can go back next year
  • Submitted: Aug 16, 2014
  • Stayed: Aug 2014