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Chesapeake Bay Pet Friendly Cottage Rentals(54)

54 Results
$250 - $400
per night
2 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
2 - 7 night minimum stay
(34)
$1,500
per week
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
7 night minimum stay
(78)
$2,132 - $2,518
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(34)

Why HomeAway?

We're the leader in vacation rentals
More than one million listings worldwide
Experienced property owners or managers
Average five years in the business
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(27)
  • 3 BR,
  • 2 BA,
  • Sleeps 9
7 night minimum stay
(5)
$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)
$100 - $175
per night
2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 night minimum stay
(3)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 7
(9)
  • 2 BR,
  • 1 BA,
  • Sleeps 5
3 night minimum stay
(12)

Why HomeAway?

We help you travel with confidence
Every listing guaranteed against fraud
We offer a best price guarantee
No booking fees and low online prices
$99 - $175
per night
1 - 4 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 3
1 - 4 night minimum stay
(18)
$137 - $260
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(25)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(12)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 Reviews
$115 - $135
per night
3 - 5 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
3 - 5 night minimum stay
(8)
$195 - $275
per night
2 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
2 - 3 night minimum stay
2 Reviews
$300
per night
2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 night minimum stay
(7)
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
7 night minimum stay
(63)
  • 3 BR,
  • 2 BA,
  • Sleeps 9
3 night minimum stay
(5)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(30)
$2,686 - $3,265
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
7 night minimum stay
(19)
  • 3 BR,
  • 3 BA,
  • Sleeps 5
7 night minimum stay
(10)
  • 7 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 14
7 night minimum stay
(3)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
7 night minimum stay
(3)
$2,511 - $3,039
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
(3)
$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
$200 - $250
per night
2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 night minimum stay
$373 - $586
per night
2 - 3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 3 night minimum stay
(31)
$200 - $250
per night
2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 7
2 night minimum stay
 

Recent Chesapeake Bay Reviews

Sisters Weekend

5 of 5
Wonderful weekend, beautiful weather, terrific sail on the Selina, shopping, Gina's Cafe for incredible tacos, and let's not forget Tilghman Island Day with music, food and working boat races!! Harbor Hideaway and St. Michaels is a special jewel on the eastern shore. Our spring visit and return in October exceeded our expectations!
  • Submitted: Oct 25, 2014
  • Stayed: Oct 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

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