Chesapeake Cottages, House Rentals & More


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Areas near Chesapeake

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1 / 19

Chesapeake Bay "BigBay" Beach House

  • 4
  • 8
  • Min stay varies

$199

Details

Great rentals within 30 miles that match your search

1 / 39

Beachy townhouse on the golf course

  • 3
  • 6
  • 7 nights min

$159

Details

1 / 33

Furnished 1BR/1.5BA Luxury Condo

  • 1
  • 2
  • 30 nights min

$103

Details

1 / 24

113 78th Street Rear

  • 5
  • 12
  • 7 nights min

$372

Details

1 / 28

NE77 118

  • 4
  • 12
  • 7 nights min

$415

Details

8
1 / 38

Mid-Century Modern Lakefront Estate: Bay & Beach

  • 2
  • 6
  • 1 night min

$127

Details

1 / 16

SEA-SUNS! A Luxurious Lakefront Retreat

  • 3
  • 10
  • Min stay varies

$249

Details

1 / 4

*New Listing for 2017

  • 4
  • 12
  • 3 nights min

$375

Details

1 / 14

Cozy 1 br near the Beach

  • 1
  • 3
  • 2 nights min

$55

Details

1
1 / 7

Cozy Mother-in-Law Suite

  • 1
  • 3
  • 2 nights min

$35

Details

1
1 / 24

1306 Dolphin Run

  • 2
  • 6
  • Min stay varies

$172

Details

1 / 55

Casa de la Familia – 7 bedroom Contemporary Hacienda Style villa with

  • 7
  • 16
  • Min stay varies

$3500

Details

1 / 18

Relaxing Chesapeake Bay Home for Rent

  • 5
  • 14
  • 2 nights min

$250

Details

2
1 / 18

Caicos Cottage "A Beach Lover's Dream"

  • 3
  • 10
  • Min stay varies

$159

Details

1 / 14

Chic's Nest is a Charming Retreat

  • 2
  • 6
  • Min stay varies

$125

Details

1
1 / 21

BEACHFRONT - $1M views and Private Beach Access

  • 3
  • 8
  • Min stay varies

$300

Details

3
1 / 21

The Bay Breeze Cottage at Lynnhaven Beach

  • 3
  • 8
  • 7 nights min

$256

Details

1 / 24

NO WORRIES

  • 2
  • 6
  • 7 nights min

$243

Details

1 / 14

2267 Powhatan Avenue

  • 2
  • 6
  • 7 nights min

$243

Details

1 / 16

Ammie's Sandcastle

  • 2
  • 6
  • 7 nights min

$172

Details

1 / 8

Wake up to a view of the Chesapeake bay, a 100 feet from sand in your toes

  • 2
  • 6
  • 4 nights min

$225

Details

14
1 / 12

2 Bedroom |Family-Friendly Vacation Rental - Walk To Beach

  • 2
  • 5
  • 1 night min

$140

Details

1 / 69

Magaly Oh ~ RA145171

  • 7
  • 28
  • 7 nights min

$555

Details

1 / 28

Beach House

  • 5
  • 10
  • 7 nights min

$400

Details

1 / 5

awesome waterfront vacation paradise spa home with pool hot tub waterfront !

  • 3
  • 6
  • Min stay varies

$550

Details

1
1 / 36

Bayberry House

  • 4
  • 13
  • 7 nights min

$286

Details

1 / 47

Costa Beach'N Cottage & the "Rain Forest Room" (possible 4th bedroom)

  • 3
  • 10
  • Min stay varies

$149

Details

1 / 11

1734 Baltic Avenue

  • 2
  • 8
  • 7 nights min

$143

Details

3
1 / 29

The Dunes at First Landing, Virginia Beach, VA

  • 3
  • 8
  • Min stay varies

$200

Details

1 / 24

Beautiful Waterfront Home w/ Boat Slip on Inlet

  • 3
  • 8
  • 21 nights min

$99

Details

2
1 / 32

Sunrise Beach Tower (Twins by the Sea)

  • 4
  • 12
  • Min stay varies

$199

Details

1
1 / 19

Sunset Tower (Horizon VA Beach)

  • 4
  • 12
  • Min stay varies

$199

Details

1 / 23

325 Mace Hill

  • 3
  • 8
  • 7 nights min

$258

Details

1
1 / 26

Beautiful 1st floor condo short walk from the Beach, famous Boardwalk and .....

  • 1
  • 4
  • Min stay varies

$43

Details

5
1 / 13

Lovely Efficiency Suite for 2 in Resort Area

  • 1
  • 2
  • 2 nights min

$69

Details

1 / 35

805 Surfside Avenue

  • 5
  • 14
  • 7 nights min

$515

Details

1 / 21

RA15 609 - Endless SUmmer

  • 3
  • 8
  • 7 nights min

$143

Details

1 / 14

Croatan Beach - Very Private Family Beach Community - Close to Ocean/Attractions

  • 4
  • 13
  • 7 nights min

$215

Details

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