Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Book Faster

Property Type

Apartments
Boats
Bungalows
Cabins
Condos
Cottages
Estates
Farmhouses
Homes
Lodges
Studios
Villas
Barns
Castles
Chalets
Hotels
Townhomes
Yachts

Book Faster

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Save time when booking: choose rentals that accept online reservations or online payments

Chesapeake Bay Vacation Rental Estates(26)

26 Results
$350 - $700
per night
2 night minimum stay
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
2 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)
$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)
$750 - $800
per night
2 - 3 night minimum stay
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 12
2 - 3 night minimum stay
(6)
  • 12 BR,
  • 8 BA,
  • 1 HF BA,
  • Sleeps 40
2 - 7 night minimum stay
(6)
$1,421 - $1,500
per night
3 - 7 night minimum stay
  • 6 BR,
  • 6 BA,
  • Sleeps 14
3 - 7 night minimum stay
(8)
$5,500
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
4 - 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,
  • 6 BA,
  • Sleeps 15
2 - 7 night minimum stay
(17)
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 12
2 - 3 night minimum stay
1 Review
  • 5 BR,
  • 7 BA,
  • Sleeps 10
(13)
$350 - $550
per night
2 - 3 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
2 - 3 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
(15)
  • 6 BR,
  • 6 BA,
  • Sleeps 12
3 - 4 night minimum stay
2 Reviews
$5,000 - $6,000
per night
3 night minimum stay
  • 8 BR,
  • 8 BA,
  • 3 HF BA,
  • Sleeps 18
3 night minimum stay
$600 - $700
per night
3 - 7 night minimum stay
  • 5 BR,
  • 4 BA,
  • Sleeps 8
3 - 7 night minimum stay
$1,000
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 BR,
  • 3 BA,
  • Sleeps 10
(3)
4 more choices from the HomeAway Network
$500 - $800
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
$1,571 - $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

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

Gorgeous Property, but Amenities need attention

4 of 5
This property is absolutely beautiful...park like setting, lots of land, beautiful waterview and spectacular sunrises. The house was comfortable...linens very clean as well as bathrooms. A few things need attention....the grill outside was unusable as the grates were covered in rust and caked on food. Also no propane. Notified the rental agent and though they tried to get new grates, they could not. But they did scrape them down a bit. Also, the A/C in the living room kept shorting out. The ceiling fan in the hot tub room did not work. I would also suggest that some things be checked between tenants...old food left in the refrigerator and dirty laundry in the washing machine. Plus ants are a definite problem. But we enjoyed the solitude and serenity as well as being so close to St. Michaels. We also appreciated how well the grounds were maintained and how clean the pool was.
  • Submitted: Sep 30, 2014
  • Stayed: Sep 2014