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Chesapeake Bay Vacation Rentals(164)

164 Results
  • 4 BR,
  • 2 BA,
  • Sleeps 9
3 - 7 night minimum stay
(26)
  • 12 BR,
  • 8 BA,
  • 1 HF BA,
  • Sleeps 40
2 - 7 night minimum stay
(8)
$350 - $450
per night
2 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 5 night minimum stay
(14)
  • 4 BR,
  • 4 BA,
  • Sleeps 8
3 - 7 night minimum stay
(35)
$525 - $690
per night
3 - 5 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 16
3 - 5 night minimum stay
(9)
  • 6 BR,
  • 6 BA,
  • Sleeps 15
2 - 7 night minimum stay
(18)
$450 - $750
per night
2 - 4 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 4 night minimum stay
(37)
  • 5 BR,
  • 4 BA,
  • Sleeps 10
2 - 7 night minimum stay
(15)
$400
per night
2 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 night minimum stay
(4)
$750 - $785
per night
3 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
(3)
$450 - $700
per night
2 night minimum stay
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
2 night minimum stay
(11)
$100 - $171
per night
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(69)
$850 - $950
per night
2 - 3 night minimum stay
  • 7 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 20
2 - 3 night minimum stay
(12)
$750 - $800
per night
2 - 3 night minimum stay
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 12
2 - 3 night minimum stay
(6)
$275 - $450
per night
3 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 11
3 night minimum stay
(8)
$350 - $450
per night
2 - 3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 3 night minimum stay
(9)
$85 - $90
per night
2 night minimum stay
  • 1 BR,
  • 1 HF BA,
  • Sleeps 2
2 night minimum stay
2 Reviews
$165 - $205
per night
2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
(6)
  • 3 BR,
  • 2 BA,
  • Sleeps 7
1 Review
$250 - $375
per night
2 - 7 night minimum stay
  • 5 BR,
  • 2 BA,
  • Sleeps 10
2 - 7 night minimum stay
1 Review
  • 4 BR,
  • 3 BA,
  • Sleeps 10
2 - 7 night minimum stay
(19)
$500 - $600
per night
2 - 5 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 8
2 - 5 night minimum stay
(19)
  • 5 BR,
  • 5 BA,
  • Sleeps 10
3 night minimum stay
(4)
$650 - $700
per night
3 - 7 night minimum stay
  • 7 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 18
3 - 7 night minimum stay
(7)
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 12
2 - 4 night minimum stay
1 Review
  • 4 BR,
  • 3 BA,
  • Sleeps 12
3 night minimum stay
2 Reviews
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 7 night minimum stay
(11)
  • 4 BR,
  • 2 BA,
  • Sleeps 10
2 - 7 night minimum stay
$899
per night
3 night minimum stay
  • 3 BR,
  • 4 BA,
  • Sleeps 10
3 night minimum stay
$250
per night
2 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 3
2 night minimum stay
 

Recent Chesapeake Bay Reviews

Spacious & Relaxing

5 of 5
This was a fantastic stay! The owners have done a wonderful job modernizing this large waterfront home. The interior is well appointed and very tastefully decorated. The pictures are spot on! We enjoyed our stay and will be back for sure! The house is very close to St. Michaels and all activities but still provides a very private waterfront experience. The home owners made every effort to make our stay comfortable and memorable.
  • Submitted: Mar 11, 2015
  • Stayed: Sep 2014

What a sensational property!

5 of 5
This home had everything we needed to hold our family Thanksgiving reunion, and, I mean everything. From comfortable bedrooms, social living space and wonderful dining and kitchen space to all of the accoutrements needed to prepare a Thanksgiving feast. The owner is meticulous with the intricacies of managing a vacation rental home, from rental engagement through post occupancy. She was accessible and proactive and made sure the home would fit our specific needs. AND the view is sensational from multiple rooms. A truly peaceful and inspiring setting. My family looks forward to retuning in the future.
  • Submitted: Dec 4, 2014
  • Stayed: Nov 2014

Sunset Haven

5 of 5
This is our first VRBO experience, and couldn't have been better. The condo was spacious and comfortable, and the views were exceptional. Loved seeing the twinkling lights from Smith and Tangier Islands at night. The wrap around deck gave it a private feel, and lots of light. Looking forward to our next stay.
  • Submitted: Oct 22, 2014
  • Stayed: Oct 2014