Woolford Vacation Rentals, Houses & More


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Areas near Woolford

1 / 17

Deerpond Carriage House

  • 1
  • 2
  • 3 nights min

$181

Details

Great rentals within 20 miles that match your search

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Manage Private Beach, Waterfront Room Rentals 2

  • 1
  • 2
  • 1 night min

$100

Details

1 / 15

BACK STREET RETREAT

  • 3
  • 6
  • Min stay varies

$343

Details

1 / 31

Stunning, Newer Chesapeake Waterfront Estate, Pool

  • 6
  • 20
  • Min stay varies

$500

Details

1 / 18

Historic Waterfront Property with Wi-Fi and Dock

  • 3
  • 8
  • 2 nights min

$750

Details

1 / 24

RESTORED WATERFRONT COTTAGE

  • 3
  • 6
  • Min stay varies

$100

Details

1 / 23

Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!

  • 2
  • 5
  • Min stay varies

$160

Details

1 / 8

Cedar Beach Lodge is a Modern Year-Round

  • 3
  • 8
  • Min stay varies

$326

Details

1 / 17

The "SWEET SPOT" - a special cottage on the Bay

  • 2
  • 4
  • 4 nights min

$145

Details

1 / 20

Tilghman Island Cottage for Six - Near Marina and Knapps Narrows Drawbridge

  • 3
  • 6
  • 3 nights min

$201

Details

1 / 8

6 Bdrm, 3.5 Bath, Cambridge Md Vacation Home

  • 6
  • 12
  • 3 nights min

$449

Details

1 / 39

Cottage at Heron Cove, Chesapeake Bay, Cambridge

  • 3
  • 5
  • Min stay varies

$201

Details

1 / 16

Choptank River View House

  • 6
  • 14
  • 3 nights min

$1001

Details

1 / 25

Waterview Cottage In St. Michaels!

  • 2
  • 5
  • Min stay varies

$160

Details

1 / 20

Fishing Cove on the Chesapeake Bay

  • 8
  • 23
  • Min stay varies

$716

Details

1 / 9

Eastern Shore Waterfront Home, Ready for Spring and Summer!

  • 3
  • 10
  • Min stay varies

$226

Details

1 / 6

Halo's Haven Guest Quarters

  • 3
  • 6
  • 2 nights min

$326

Details

1 / 44

Private Beach, Waterfront Room Rentals 3

  • 1
  • 2
  • 2 nights min

$100

Details

1 / 27

Location Location! St Michaels-- In Town Cottage!

  • 2
  • 5
  • Min stay varies

$150

Details

1 / 24

Premier Cottage in St. Michaels- In Town Location!

  • 2
  • 5
  • Min stay varies

$150

Details

1 / 34

Grandview at Pleasure Point

  • 8
  • 27
  • 7 nights min

$902

Details

1 / 7

St. Michael's Premier in Town Summer Cottage!

  • 2
  • 4
  • 2 nights min

$285

Details

1 / 20

Best kept secret by the bay (Entire House)

  • 3
  • 4
  • 3 nights min

$170

Details

1 / 24

My Chesapeake Retreat 27 acre waterfront estate

  • 4
  • 12
  • 3 nights min

$900

Details

1 / 29

Cedar Beach Lodge

  • 3
  • 8
  • 2 nights min

$401

Details

1 / 30

Large Historic Thomas Harrison House on Harbor in St. Michaels Town

  • 7
  • 9
  • Min stay varies

$290

Details

1 / 22

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

  • 4
  • 10
  • Min stay varies

$376

Details

1 / 10

Harbor Cottage at the Chesapeake Bay

  • 2
  • 6
  • 3 nights min

$260

Details

1 / 55

Waterfront Vacation Home with Private Beach

  • 3
  • 6
  • 2 nights min

$331

Details

1 / 6

Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX

  • 1
  • 6
  • 2 nights min

$229

Details

1 / 38

Hoopers Island Studio, 360 Degrees WATER VIEWS

  • 1
  • 3
  • 3 nights min

$134

Details

1 / 4

A cozy room in Lusby

  • 1
  • 1
  • 1 night min

$51

Details

1 / 18

St. Michaels Waterfront Home W/Dock for 2 boats

  • 2
  • 5
  • Min stay varies

$250

Details

1 / 19

A waterfront vacation rental located on the Chesapeake Bay

  • 5
  • 11
  • Min stay varies

$201

Details

1 / 22

Cedar Point Chesapeake Bay Waterfront Cottage

  • 3
  • 9
  • 2 nights min

Inquire for Rates

Details

1 / 35

Year Round Estate on Bay / Fam. Reunions / Slps 28

  • 7
  • 28
  • Min stay varies

$1201

Details

1 / 34

Private Beach, Waterfront Room Rentals 1

  • 1
  • 2
  • 2 nights min

$130

Details

1 / 15

Tranquil Easton Waterfront Property

  • 3
  • 6
  • 3 nights min

$600

Details

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