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Chesapeake Bay Pet Friendly Vacation Rentals(176)

176 Results
$450 - $750
per night
2 - 4 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 4 night minimum stay
(34)
$745 - $1,250
per night
3 - 7 night minimum stay
  • 5 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 7 night minimum stay
(17)
  • 6 BR,
  • 6 BA,
  • Sleeps 15
2 - 7 night minimum stay
(17)
$550 - $707
per night
3 - 7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 16
3 - 7 night minimum stay
(9)
$850 - $950
per night
2 - 3 night minimum stay
  • 7 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 20
2 - 3 night minimum stay
(11)
$275 - $450
per night
3 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 11
3 night minimum stay
(7)
$350 - $450
per night
2 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 5 night minimum stay
(14)
$829 - $950
per night
2 - 7 night minimum stay
  • 5 BR,
  • 6 BA,
  • 2 HF BA,
  • Sleeps 10
2 - 7 night minimum stay
(5)
$1,143 - $2,300
per night
3 - 7 night minimum stay
  • 7 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 28
3 - 7 night minimum stay
(7)
$700 - $2,250
per night
3 - 7 night minimum stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 18
3 - 7 night minimum stay
(9)
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 15
3 night minimum stay
(7)
$250 - $400
per night
2 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
2 - 7 night minimum stay
(34)
$5,500
per week
7 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 8
7 night minimum stay
(6)
  • 3 BR,
  • 2 BA,
  • Sleeps 9
7 night minimum stay
(5)
$185 - $350
per night
3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
2 Reviews
$750 - $785
per night
3 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
(3)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
3 night minimum stay
(78)
$434 - $436
per night
2 night minimum stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
2 night minimum stay
(63)
$439 - $441
per night
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 night minimum stay
(34)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
3 night minimum stay
(27)
  • 7 BR,
  • 7 BA,
  • 1 HF BA,
  • Sleeps 22
2 night minimum stay
(18)
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 night minimum stay
(27)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
(34)
  • 4 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
(43)
$400 - $600
per night
2 - 5 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 8
2 - 5 night minimum stay
(19)
$650 - $700
per night
3 - 7 night minimum stay
  • 7 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 18
3 - 7 night minimum stay
(7)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 7 night minimum stay
(11)
$555 - $1,167
per night
3 - 7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
3 - 7 night minimum stay
(30)
$467 - $468
per night
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 night minimum stay
(51)
$505 - $507
per night
2 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 7
2 night minimum stay
(43)
 

Recent Chesapeake Bay Reviews

The best week ever.

5 of 5
I can't remember enjoying a week more. The house is beautiful, one can tell great care was used in selecting the furnishings. Everything is of the highest quality and yet comfortable and relaxing at the same time. The kitchen is well-equipped, I found everything I wanted, and the view from the breakfast table is glorious. One feels at home. The water is right at the edge of the property, a stroll to the dock always rewarded the birdwatcher. Total privacy and yet the town of St. Michael's has great restaurants, intriguing shops, and local history to delve into, and it's just minutes away.
  • Submitted: Dec 3, 2014
  • Stayed: Nov 2014

Absolutely Perfect

5 of 5
I just returned from a guys' getaway weekend here and was thrilled with the experience. It was such a slice of heaven that nobody wanted to leave! Amos and Liz have really thought of everything in terms of comforts (plenty of towels, yard games in the garage, kayaks, wifi, DirecTV, etc etc). The photos on here don't do it justice (nor do the ones I took myself) because you just can't capture the 360 degrees of awesomeness surrounding you at all times. I'll definitely be back!
  • Submitted: Oct 28, 2014
  • Stayed: Oct 2014

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