Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Book Faster

Property Type

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

Book Faster

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Chesapeake Bay House Rentals(180)

180 Results
$35 - $350
per night
3 - 6 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 6 night minimum stay
(4)
$795 - $995
per night
2 night minimum stay
  • 5 BR,
  • 4 BA,
  • Sleeps 10
2 night minimum stay
  • 5 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 7 night minimum stay
2 Reviews
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
2 Reviews
$900
per night
3 night minimum stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
3 night minimum stay
2 Reviews
  • 4 BR,
  • 5 BA,
  • Sleeps 10
3 - 4 night minimum stay
$795 - $995
per night
2 night minimum stay
  • 5 BR,
  • 4 BA,
  • Sleeps 10
2 night minimum stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
7 night minimum stay
1 Review
$1,351
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
7 night minimum stay
(13)
$750
per night
3 night minimum stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 13
3 night minimum stay
2 Reviews
  • 4 BR,
  • 1 BA,
  • Sleeps 8
2 - 7 night minimum stay
(8)
  • 4 BR,
  • 4 BA,
  • Sleeps 8
2 night minimum stay
2 Reviews
$250 - $300
per night
2 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
2 night minimum stay
(8)
  • 6 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
(10)
$350
per night
4 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
4 night minimum stay
1 Review
$3,000
per month
90 night minimum stay
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 8
90 night minimum stay
$275 - $350
per night
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
2 night minimum stay
2 Reviews
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 17
(12)
$1,379 - $1,500
per night
3 - 7 night minimum stay
  • 7 BR,
  • 5 BA,
  • Sleeps 12
3 - 7 night minimum stay
$950 - $1,110
per night
3 - 6 night minimum stay
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 6 night minimum stay
$375
per night
4 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
4 night minimum stay
(3)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 Reviews
$200
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(4)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
1 Review
  • 2 BR,
  • 1 BA,
  • Sleeps 5
7 night minimum stay
(5)
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 13
(7)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 9
3 night minimum stay
1 Review
  • 2 BR,
  • 1 BA,
  • Sleeps 6
3 night minimum stay
2 Reviews
$260 - $314
per night
5 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
5 - 7 night minimum stay
  • 6 BR,
  • 3 BA,
  • Sleeps 12
(3)
 

Recent Chesapeake Bay Reviews

Beautiful property with wonderful location

5 of 5
2014 was our 5th year at this amazing house. It has eveything you could want for a vacation and our family really enjoy staying here. The listing description is accurate so too is all the other information about the property. The location is serene and beautiful and the house is stunning, the pool is loved by us all and the surrounding area is very interesting. We have just booked for our 6th year and can't wait to return. We are more than happy to recommend this property to any prospective renters.
  • Submitted: Dec 30, 2014
  • Stayed: Jul 2014

Amazing house

5 of 5
I would highly recommend this house. The location is awesome, the house is large and comfortable. We had 6 people share the house and had plenty of space for the two families which shared the house. We were participating in a baseball tournament at Ripken in Aberdeen. The house was a nice break from all the baseball that week. Lots of room to have your own privacy while still enjoying the bay. Tina, the owner, was responsive and helpful. The house is well kept and very clean. The only thing you should know is you have to pay $8 to cross the bridge to get to this house. you only need to pay going to the house, but if you go over the bridge 2x or more times a day it does add up. But honestly, the unplanned expense was well worth it. The location is amazing, and the house is beautiful. If we every come back to the area, I would stay in this house again! No doubt!
  • Submitted: Oct 18, 2014
  • Stayed: Jul 2014

We felt so comfortable and did't want to leave

5 of 5
What a wonderful surprise to walk into this lovely home, everything was perfect. There were 5 of us and we all felt comfortable. I loved all of the decor and the colors were very tasteful. The location was perfect also. Everything you needed or wanted was already in the house, so we didn't have to worry about anything. Would love to go back and stay awhile
  • Submitted: Oct 2, 2014
  • Stayed: Sep 2014