Preston Vacation Rentals, Houses & More


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IRONMAN AND 5KERS

  • 1
  • 2
  • 1 night min

$87

Details

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EASTERN SHORE MARYLAND WELCOMES YOU

  • 1
  • 2
  • 1 night min

$75

Details

Great rentals within 30 miles that match your search

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Waterfront Vacation Home with Private Beach

  • 3
  • 6
  • 2 nights min

$330

Details

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Private Beach, Waterfront Room Rentals 1

  • 1
  • 2
  • 2 nights min

$130

Details

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Manage Private Beach, Waterfront Room Rentals 2

  • 1
  • 2
  • 1 night min

$100

Details

1 / 44

Private Beach, Waterfront Room Rentals 3

  • 1
  • 2
  • 2 nights min

$100

Details

1 / 15

Tranquil Easton Waterfront Property

  • 3
  • 6
  • 3 nights min

$600

Details

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Choptank River View House

  • 6
  • 14
  • 3 nights min

$1000

Details

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6 Bdrm, 3.5 Bath, Cambridge Md Vacation Home

  • 6
  • 12
  • 3 nights min

$449

Details

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My Chesapeake Retreat 27 acre waterfront estate

  • 4
  • 12
  • 3 nights min

$900

Details

10
1 / 24

RESTORED WATERFRONT COTTAGE

  • 3
  • 6
  • Min stay varies

$100

Details

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BACK STREET RETREAT

  • 3
  • 6
  • Min stay varies

$350

Details

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Historic Waterfront Property with Wi-Fi and Dock

  • 3
  • 8
  • 2 nights min

$750

Details

2
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Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX

  • 1
  • 6
  • 2 nights min

$230

Details

8
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Cottage at Heron Cove, Chesapeake Bay, Cambridge

  • 3
  • 5
  • Min stay varies

$200

Details

11
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Large Historic Thomas Harrison House on Harbor in St. Michaels Town

  • 7
  • 9
  • Min stay varies

$390

Details

3
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Waterview Cottage In St. Michaels!

  • 2
  • 5
  • Min stay varies

$215

Details

12
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Premier Cottage in St. Michaels- In Town Location!

  • 2
  • 5
  • Min stay varies

$205

Details

4
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Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!

  • 2
  • 5
  • Min stay varies

$160

Details

21
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Location Location! St Michaels-- In Town Cottage!

  • 2
  • 5
  • Min stay varies

$195

Details

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RusTic BaRn- GlAmPing- 2Br in Country near BEACHES

  • 2
  • 12
  • 1 night min

$118

Details

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Sun and Sand Loft- just minutes to the beach:) Hot tub

  • 1
  • 4
  • 1 night min

$118

Details

2
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Fishing Cove on the Chesapeake Bay

  • 8
  • 23
  • Min stay varies

$715

Details

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St. Michaels award-winning waterfront BayCottage, pool, docks, sundeck, grounds

  • 6
  • 12
  • Min stay varies

$780

Details

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***ApARtMent-PrivaTe GeTaWay-, minutes to Rehoboth, Kitchen &H.TuB &Pet friendly

  • 1
  • 8
  • 1 night min

$199

Details

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Apartment- 2 BR, minutes to Rehoboth, Hot Tub, country getaway:)

  • 2
  • 10
  • 1 night min

$209

Details

1 / 132

Nature Retreat- Awesome Studio Apartment- Just Minutes to Beach:) 2 Beds, H.Tub

  • 1
  • 8
  • 1 night min

$145

Details

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Halo's Haven Guest Quarters

  • 3
  • 6
  • 2 nights min

$325

Details

5
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Cedar Point Chesapeake Bay Waterfront Cottage

  • 3
  • 9
  • 2 nights min

$650

Details

1
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St. Michaels Waterfront Home W/Dock for 2 boats

  • 2
  • 5
  • Min stay varies

$250

Details

10
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Grandview at Pleasure Point

  • 8
  • 27
  • 7 nights min

$901

Details

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Deerpond Carriage House

  • 1
  • 2
  • 3 nights min

$180

Details

4
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Sandy Pines: Enjoy Harris Creek w/Pool and Boats

  • 4
  • 10
  • Min stay varies

$375

Details

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Charming Coastal Cottage Minutes to St. Michaels

  • 2
  • 6
  • Min stay varies

$175

Details

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Halos'Haven Vacation Rental

  • 5
  • 10
  • 2 nights min

$700

Details

5
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ENDLESS SUNSETS - The perfect getaway!

  • 3
  • 8
  • Min stay varies

$275

Details

3
1 / 35

Comfortable, Spacious & Fun! 6 Acres Pool & Shore

  • 5
  • 10
  • 3 nights min

$1000

Details

6
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Tilghman Island Cottage for Six - Near Marina and Knapps Narrows Drawbridge

  • 3
  • 6
  • 3 nights min

$200

Details

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