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Chesapeake Bay Vacation Rental Estates(27)

27 Results
  • 12 BR,
  • 8 BA,
  • 1 HF BA,
  • Sleeps 40
2 - 7 night minimum stay
(8)
  • 6 BR,
  • 6 BA,
  • Sleeps 15
2 - 7 night minimum stay
(18)
$350 - $700
per night
2 night minimum stay
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
2 night minimum stay
(6)
$750 - $800
per night
2 - 3 night minimum stay
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 12
2 - 3 night minimum stay
(6)
$850 - $950
per night
2 - 3 night minimum stay
  • 7 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 20
2 - 3 night minimum stay
(11)
$1,421 - $1,500
per night
3 - 7 night minimum stay
  • 6 BR,
  • 6 BA,
  • Sleeps 14
3 - 7 night minimum stay
(8)
$850 - $1,100
per night
2 night minimum stay
  • 5 BR,
  • 6 BA,
  • 2 HF BA,
  • Sleeps 10
2 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)
$6,500
per week
7 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 8
7 night minimum stay
(6)
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 12
7 night minimum stay
(6)
$1,200 - $3,500
per night
3 - 7 night minimum stay
  • 10 BR,
  • 6 BA,
  • 2 HF BA,
  • Sleeps 36
3 - 7 night minimum stay
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 12
2 - 4 night minimum stay
1 Review
  • 5 BR,
  • 7 BA,
  • Sleeps 10
(13)
$400 - $600
per night
2 - 6 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
2 - 6 night minimum stay
(12)
$650 - $1,000
per night
3 - 4 night minimum stay
  • 4 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 10
3 - 4 night minimum stay
(3)
$1,200 - $2,000
per night
2 - 7 night minimum stay
  • 8 BR,
  • 7 BA,
  • 2 HF BA,
  • Sleeps 20
2 - 7 night minimum stay
(16)
  • 6 BR,
  • 6 BA,
  • Sleeps 12
3 - 4 night minimum stay
2 Reviews
  • 6 BR,
  • 3 BA,
  • Sleeps 12
3 - 7 night minimum stay
1 Review
$5,000 - $18,000
per night
1 - 3 night minimum stay
  • 8 BR,
  • 8 BA,
  • 3 HF BA,
  • Sleeps 18
1 - 3 night minimum stay
$600 - $857
per night
3 - 7 night minimum stay
  • 5 BR,
  • 4 BA,
  • Sleeps 8
3 - 7 night minimum stay
$1,300
per night
3 - 7 night minimum stay
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 7 night minimum stay
  • 8 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 15
(3)
5 more choices from the HomeAway Network
$500 - $856
per night
2 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
2 - 7 night minimum stay
(43)
$750 - $975
per night
3 night minimum stay
  • 5 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 10
3 night minimum stay
2 Reviews
$1,000 - $1,250
per night
2 - 7 night minimum stay
  • 10 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 26
2 - 7 night minimum stay
(4)
$1,571 - $2,998
per night
2 night minimum stay
  • 11 BR,
  • 8 BA,
  • 1 HF BA,
  • Sleeps 27
2 night minimum stay
1 Review
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 12
1 Review
 

Recent Chesapeake Bay Reviews

Unbelievable Vacation Retreat

5 of 5
The house & property were even more beautiful in person. The house was immaculate & very well stocked. Location was unbelievable with incredible waterfront views & memorable evening sunsets. The dock, pool, pool house & extensive lawn provided many happy hours of entertainment. The town of St. Michael's is lovely but mostly we stayed at the house as no one wanted to leave. The owner & caretaker were very accommodating. My children & grandchildren said it was the best vacation ever. Would highly recommend. Hope to return.
  • Submitted: Dec 27, 2014
  • Stayed: Aug 2014

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

Wonderful!

5 of 5
Our stay at the Last Resort was wonderful! We had three generations gather in November and we couldn't have imagined a nicer setting. The interior layout is open with breathtaking views of the Chesapeake Bay from almost every room! We loved using the fully equipped kitchen, sound system, media room, pool table and workout room. It was also nice to get outside and walk the property as well as explore the charming nearby towns of St Michael's and Easton. Both the owners and the realty company could not have been more responsive to any of our concerns or questions. This is exactly what you hope for when you rent a wonderful home for your family! We are already beginning to plan a return trip in warmer weather to enjoy the outdoor pool and kayaks!
  • Submitted: Nov 24, 2014
  • Stayed: Nov 2014