Smith Island Vacation Rentals, Houses & More


1 - 38 of 38

View larger map

Great rentals within 30 miles that match your search

1 / 21

The Relax-Inn Deal Island

  • 3
  • 6
  • 3 nights min

$125

Details

1
1 / 22

Chesapeake Bay Sunrises AND Sunsets

  • 2
  • 6
  • 2 nights min

$150

Details

3
1 / 21

Water water everywhere in this gorgeous home

  • 3
  • 8
  • 2 nights min

$250

Details

1 / 24

Secluded Private Mansion Estate's 'Bayhouse'

  • 5
  • 12
  • Min stay varies

$325

Details

1 / 18

The Premier

  • 1
  • 2
  • 1 night min

$195

Details

2
1 / 26

I Love To Fish Cottage On Chesapeake Bay

  • 3
  • 6
  • Min stay varies

$225

Details

5
1 / 29

Heron Point, Home on Chespeake Bay, Reedville, VA

  • 4
  • 9
  • 3 nights min

$375

Details

2
1 / 16

Little Wicomico Cottage

  • 3
  • 8
  • 1 night min

$180

Details

1 / 22

Bridge Creek Retreat

  • 5
  • 10
  • 3 nights min

$275

Details

1 / 20

My Blue Heaven

  • 6
  • 16
  • 2 nights min

$400

Details

1 / 22

Meticulous Waterfront Home

  • 6
  • 16
  • 3 nights min

$565

Details

17
1 / 17

RELAXING QUAINT FARM HOUSE- RIVER RETREAT- FISHING & CRABBING ON SLOOP CREEK

  • 4
  • 10
  • Min stay varies

$275

Details

1 / 37

Sunrise Point Waterfront Family Vacation

  • 3
  • 8
  • 3 nights min

$215

Details

3
1 / 26

Chesapeake Bay Beach House in Reedville Virginia

  • 5
  • 14
  • Min stay varies

$400

Details

1 / 23

Fishermans House - 12 miles from Reedville, Va

  • 3
  • 6
  • 2 nights min

$135

Details

1 / 19

Charming Rustic Waterfront Home with Spectacular Views

  • 2
  • 6
  • 2 nights min

$150

Details

1 / 9

Eastern Shore Waterfront Home, Ready for Spring and Summer!

  • 3
  • 10
  • Min stay varies

$225

Details

4
1 / 20

Best kept secret by the bay (Entire House)

  • 3
  • 4
  • 3 nights min

$169

Details

2
1 / 38

Hoopers Island Studio, 360 Degrees WATER VIEWS

  • 1
  • 3
  • 3 nights min

$133

Details

1 / 19

A waterfront vacation rental located on the Chesapeake Bay

  • 5
  • 11
  • Min stay varies

$200

Details

2
1 / 33

New! 4 BR House on St George Island w/Great Views!

  • 4
  • 12
  • 4 nights min

$225

Details

1 / 13

Leisure Cove

  • 4
  • 9
  • 2 nights min

$300

Details

1 / 48

Waterfront 5BR Farmhouse w/pool

  • 5
  • 9
  • Min stay varies

$275

Details

1 / 49

Waterfront 5BR Farmhouse w/pool & 2BR/1BA cottage

  • 7
  • 14
  • Min stay varies

$400

Details

1 / 15

Tween Cottage On Lower Potomac At Sandy Point

  • 4
  • 8
  • Min stay varies

$250

Details

27
1 / 14

Parker Shores

  • 3
  • 11
  • 2 nights min

$165

Details

45
1 / 17

Shannon Point Lodge Peaceful and Private

  • 4
  • 13
  • 2 nights min

$165

Details

17
1 / 19

Chesapeake Bay "BigBay" Beach House

  • 4
  • 8
  • Min stay varies

$199

Details

7
1 / 13

The LoveShack

  • 2
  • 6
  • Min stay varies

$191

Details

6
1 / 36

My Pan-O-Sea-A on the Chesapeake Bay.

  • 2
  • 6
  • 2 nights min

$200

Details

1
1 / 14

Seahaven

  • 3
  • 8
  • 2 nights min

$275

Details

1
1 / 4

Little Bay Waterfront Home with Private Beach

  • 3
  • 6
  • 2 nights min

$200

Details

1
1 / 6

Secluded Waterfront Home

  • 3
  • 6
  • 2 nights min

$225

Details

1 / 26

Potomac River Woodland Cottage with Old World Charm, near St. Mary's City

  • 3
  • 6
  • Min stay varies

$150

Details

1 / 31

Blue Heron Bay

  • 4
  • 10
  • Min stay varies

$180

Details

1 / 16

BELLE HAVEN COTTAGE

  • 2
  • 7
  • 3 nights min

$150

Details

1 / 16

Eagle Sound

  • 3
  • 6
  • Min stay varies

$191

Details

1 / 6

Irvington Cottage #7 at the Vineyard

  • 3
  • 6
  • 2 nights min

$225

Details

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more
See only the properties that can be booked online with Payment Protection.
Learn more