Chestertown Vacation Home Rentals, Treehouses & more


1 - 17 of 17

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Areas near Chestertown

Great rentals within 20 miles that match your search

1 / 11

Love Point Bay Vacation Home

  • 2
  • 6
  • 2 nights min

$210

Details

1 / 15

Waterfront Cottage at Spring Cove

  • 3
  • 6
  • 3 nights min

$249

Details

1 / 12

Captain's Quarters, a waterfront couples retreat

  • 1
  • 4
  • 2 nights min

$181

Details

1 / 20

Love Point Waterfront

  • 3
  • 12
  • 3 nights min

$201

Details

1 / 17

* 3 Bedroom Rental House in Historic Rock Hall MD

  • 3
  • 7
  • 2 nights min

$250

Details

1 / 39

Love Point Bay Vacation Home

  • 2
  • 6
  • 2 nights min

$300

Details

1 / 34

Waterfront House, Eastern Shore Chesapeake Bay

  • 4
  • 8
  • Min stay varies

$351

Details

1 / 12

Love Point Bay Luxury Waterfront House

  • 3
  • 10
  • 3 nights min

$894

Details

1 / 12

Sailors Crossing

  • 3
  • 10
  • 1 night min

$333

Details

1 / 35

Luxury vacation condominum with private beach

  • 4
  • 10
  • 2 nights min

$437

Details

1 / 10

Charming Apartment in Historic Chestertown, MD

  • 1
  • 2
  • Min stay varies

$46

Details

1 / 7

Cozy Apartment in Chestertown

  • 1
  • 2
  • Min stay varies

$99

Details

1 / 28

Bayview by Chesapeake Bay

  • 1
  • 4
  • Min stay varies

$130

Details

1 / 14

Retreat at a quiet, water front cottage

  • 3
  • 8
  • 2 nights min

$295

Details

1 / 11

Chester River House with Views

  • 3
  • 7
  • 2 nights min

$155

Details

1 / 22

Sunview Cottage on Chesapeake Bay

  • 2
  • 5
  • Min stay varies

$88

Details

1 / 16

Gorgeous Home on Chester River

  • 4
  • 8
  • 3 nights min

$651

Details

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