91 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Booking Options

Location Type

Even More Filters

Features

Managed By

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

Chesapeake Bay Beach Vacation Rentals(91)

91 Results
$350 - $450
per night
2 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 5 night minimum stay
(14)
$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)
$250 - $400
per night
2 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
2 - 7 night minimum stay
(34)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 7 night minimum stay
(11)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
1 Review
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 Reviews
  • 2 BR,
  • 1 BA,
  • Sleeps 5
7 night minimum stay
(5)
  • 6 BR,
  • 3 BA,
  • Sleeps 12
(3)
$35 - $350
per night
3 - 6 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 6 night minimum stay
(4)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 7 night minimum stay
(27)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 3 night minimum stay
(12)
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 12
(25)
  • 4 BR,
  • 3 BA,
  • Sleeps 10
(25)
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 - 7 night minimum stay
(8)
  • 4 BR,
  • 2 BA,
  • Sleeps 10
(10)
  • 2 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 6
3 night minimum stay
(4)
  • 4 BR,
  • 4 BA,
  • Sleeps 14
1 Review
  • 2 BR,
  • 1 BA,
  • Sleeps 5
3 night minimum stay
(12)
$99 - $175
per night
1 - 4 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 3
1 - 4 night minimum stay
(18)
$2,400 - $2,900
per week
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 12
7 night minimum stay
(4)
$137 - $260
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(25)
  • 2 BR,
  • 1 BA,
  • Sleeps 5
2 - 6 night minimum stay
(26)
$450 - $975
per night
2 night minimum stay
  • 5 BR,
  • 5 BA,
  • Sleeps 10
2 night minimum stay
(3)
$221 - $250
per night
2 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 12
2 - 7 night minimum stay
(23)
$243 - $350
per night
3 - 7 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 6
3 - 7 night minimum stay
(7)
$1,350
per week
3 - 7 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 6
3 - 7 night minimum stay
2 Reviews
$271 - $300
per night
3 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 10
3 - 5 night minimum stay
(14)
$195 - $275
per night
2 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
2 - 3 night minimum stay
2 Reviews
$300
per night
2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 night minimum stay
(7)
 

Recent Chesapeake Bay Reviews

Very Nice Place!!!

5 of 5
The home is beautiful and has everything you need to cook in the big top notch kitchen! Everything was very clean and made you feel rite at home we will be back every year for the same week!!
  • Submitted: Jan 19, 2015
  • Stayed: Jan 2015

Sisters Weekend

5 of 5
Wonderful weekend, beautiful weather, terrific sail on the Selina, shopping, Gina's Cafe for incredible tacos, and let's not forget Tilghman Island Day with music, food and working boat races!! Harbor Hideaway and St. Michaels is a special jewel on the eastern shore. Our spring visit and return in October exceeded our expectations!
  • Submitted: Oct 25, 2014
  • Stayed: Oct 2014

Very nice . . .

5 of 5
Our stay at the cottage was not long enough. The tasteful decorations, supplies on hand combined with the beautiful weather made our first trip to this area a memorable one. Our dog had a fantastic time playing in the water, running the beach and trying to catch sea creatures. The deck off the side was just right for coffee, cocktails and talking. The overall peace and tranquility of the area was amazing. We are looking forward to returning next year. Thank you for helping us celebrate our trip.
  • Submitted: Oct 3, 2014
  • Stayed: Sep 2014