Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Location Type

Even More Filters

Features

Managed By

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

Chesapeake Bay Vacation Rentals with Air Conditioning(313)

313 Results
  • 4 BR,
  • 2 BA,
  • Sleeps 9
3 - 7 night minimum stay
(26)
  • 5 BR,
  • 4 BA,
  • Sleeps 10
3 night minimum stay
(24)
$434 - $515
per night
2 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
2 - 3 night minimum stay
(63)
$450 - $550
per night
2 - 3 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 3 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
(16)
  • 4 BR,
  • 2 BA,
  • Sleeps 8
2 - 3 night minimum stay
(43)
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 3 night minimum stay
(27)
$234 - $390
per night
2 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 - 3 night minimum stay
(78)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 night minimum stay
(9)
$908 - $1,144
per night
2 - 3 night minimum stay
  • 7 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 22
2 - 3 night minimum stay
(43)
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 13
2 - 3 night minimum stay
(25)
  • 7 BR,
  • 7 BA,
  • 1 HF BA,
  • Sleeps 22
2 - 3 night minimum stay
(18)
$538 - $629
per night
2 - 3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 3 night minimum stay
(34)
$439 - $632
per night
2 - 3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 3 night minimum stay
(34)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
3 night minimum stay
(27)
  • 5 BR,
  • 5 BA,
  • Sleeps 12
4 night minimum stay
(13)
$850 - $950
per night
2 - 3 night minimum stay
  • 7 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 20
2 - 3 night minimum stay
(9)
$739 - $892
per night
2 - 3 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 10
2 - 3 night minimum stay
(9)
$500 - $800
per night
3 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 16
3 night minimum stay
(9)
  • 4 BR,
  • 4 BA,
  • Sleeps 8
3 - 7 night minimum stay
(33)
$400
per night
2 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 night minimum stay
(3)
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 12
3 - 4 night minimum stay
(6)
$100 - $171
per night
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(68)
$1,136 - $1,421
per night
3 - 7 night minimum stay
  • 6 BR,
  • 6 BA,
  • Sleeps 14
3 - 7 night minimum stay
(8)
$350 - $700
per night
2 night minimum stay
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
2 night minimum stay
(5)
$700 - $800
per night
2 - 3 night minimum stay
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 12
2 - 3 night minimum stay
(6)
$350 - $425
per night
2 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 5 night minimum stay
(14)
$750 - $1,500
per night
3 - 7 night minimum stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 18
3 - 7 night minimum stay
(9)
$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)
$871 - $950
per night
2 - 7 night minimum stay
  • 5 BR,
  • 6 BA,
  • 2 HF BA,
  • Sleeps 10
2 - 7 night minimum stay
(5)
 

Recent Chesapeake Bay Reviews

Decompress and enjoy the view!

5 of 5
Harbour Lights boasts a beautifully situated condo overlooking the bay, with crab and oyster boat activity to view throughout the day. Gorgeous views from many areas in the condo. Lovely to be able to walk throughout the marina and also to watch the sunsets from the balcony. Condo is very spacious and is tastefully decorated, allowing the guest to being very comfortable. Kitchen very well equipped. Great getaway for adults.
  • Submitted: Oct 8, 2014
  • Stayed: Oct 2014

Great house in great location

5 of 5
The house and grounds were lovely, and the town of Oxford was very charming as well. The caretaker was available to help with all questions, and the house was well-stocked. I highly recommend this rental.
  • Submitted: Sep 29, 2014
  • Stayed: Sep 2014

ENJOY STAY 2 YEAR WAS JUST AS FUN AS THE 1

5 of 5
IT WAS GREAT THE WEEK WAS FUN,RELAXING AND A GOOD BONDING EXPERIENCE WITH THE FAMILY. THE ONLY BEEF IS WITH THE BBQ, GAS CONTAINER, IT WAS EMPTY AND JUST HAD GOTTEN TO THE HOUSE AFTER A LONG RIDE, HAD TO RUN OUT AND GET IT FILLED 30.00 FOR GAS.
  • Submitted: Aug 7, 2014
  • Stayed: Jul 2014