St. Leonard Rentals

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11 Houses

Cozy Cedar Cottage near the Chesapeake Bay

Saint Leonard house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$150

Quiet Cottage, Hot Tub, Bay View, Block to Beach, 1hr to DC

Saint Leonard house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$251

Great rentals within 20 miles that match your search

The Legends Getaway

Bryantown house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$604

Private Beach Community Home

Lusby house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$161

Cozy Catalina Cabin

Lusby house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

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Price per night from

$259

Huge Beach Bungalow- Yard, Beach Pass, King Beds

North Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$633

Beautiful Waterfront Home, Private Pool and Water Amenities- Sleeps 16

Cambridge house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 18

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Price per night from

$863

Cottage at Heron Cove, Chesapeake Bay, Cambridge

Cambridge cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 32 minutes

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Price per night from

$257

Breathtaking Waterfront Cambridge Getaway

Cambridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$682

Stunning, Newer Chesapeake Waterfront Estate, Pool - 7 Bedrms 5 Baths

Cambridge house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 18

“Outstanding Vacation Rental” Our extended family (22 people - 13A/9K) had a great week at Saddle Beach. The house was beautiful and in very good condition. The option of being in the pool or the river during the day was wonderful. The house was clean and well furnished. The dining room table and table on the porch provided plenty of seating for meals. There was plenty of hot water for showers and clean-up after meals. The pool was clean and the river was awesome, with a gradual slope that was perfect for kids and adults. We used the crab traps provided and caught 2 dozen crabs that made a great contribution to dinner on Friday. Crabbing was best by the dock. We caught all but 3 crabs there, rather than out closer to the middle of the river. The AC on the ground floor stopped working on Tuesday, but one call to the owner and the repair team was on-site in less than 2 hours. The issue was resolved before noon on Wednesday. We have been renting vacation properties for years and issues crop up from time to time. We appreciated the quick response and resolution. The one recommendation we will make is to bring bug spray (mosquitos and horse flies). We anticipated it being right on the river, but if you haven't had that experience, you need to be prepared.

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Price per night from

$1,030

Retreat at Fenwick

Leonardtown apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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Price per night from

$124

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