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St. Leonard Rentals

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Price range

Per night

$10 - $500

Rental types

St. Leonard Rentals

17 Houses

New! Beachfront 4BR St. Leonard Cottage w/ Deck!

Saint Leonard cottage

4 bedrooms / 1 bathroom / sleeps 8

Responds fast! avg. 10 minutes

Price per night from

$159

1 / 24

Harbor Cottage at the Chesapeake Bay

Saint Leonard cottage

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$260

1 / 10

Charming 1BR Saint Leonard Bungalow Overlooking Wells Cove

Saint Leonard cottage

1 bedroom / / sleeps 2

Responds fast! avg. 10 minutes

Price per night from

$90

1 / 13

Great rentals within 20 miles that match your search

Best kept secret by the bay (Entire House)

Fishing Creek house

3 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 33 minutes

Price per night from

$168

1 / 20

Chesapeake Beach Apt. Walk to Bay, Beach & Marina!

Chesapeake Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 10 minutes

Price per night from

$70

1 / 24

Seahorse Guest Cottage near the Bay, dog friendly

North Beach cottage

1 bedroom / 1 bathroom / sleeps 5

Responds fast! avg. 12 minutes

Price per night from

$159

1 / 17

Chesapeake Bay Waterfront on Hoopers Island with Private Beach

Fishing Creek house

5 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$295

1 / 33

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

Tilghman cottage

3 bedrooms / 2 bathrooms / sleeps 6

“We loved it!” We had a great (albeit too short!) family getaway at the Roost! The cottage is extremely clean, comfortable, well-maintained, and spacious. The kids (ages 6 and 20 months) loved it -- especially the bunk beds and the nice backyard, and t

Price per night from

$199

1 / 20

Panoramic Views of Herrington Harbour on the Bay.

North Beach house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$500

1 / 11

Renovated Luxury Waterview House

North Beach house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$296

1 / 9

Stunning, Newer Chesapeake Waterfront Estate, Pool - 6/7 Bedrms 5 Baths

Cambridge house

6 bedrooms / 5 bathrooms / sleeps 20

“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 cle

Responds fast! avg. 3 hours 27 minutes

Price per night from

$493

1 / 31

Hoopers Island Studio, 360 Degrees WATER VIEWS

Fishing Creek apartment

1 bedroom / 1 bathroom / sleeps 3

“What a fantastic stay!” As soon as we stepped out of our car, we felt like we hit the jackpot. The views in front and in back of the house are breathtaking, with water stretching to the horizons. Inside the house, we found all that we could need and

Responds fast! avg. 1 hour 35 minutes

Price per night from

$155

1 / 38

Business or Leisure?

Lusby guest house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 37 minutes

Price per night from

$65

1 / 10

Eastern Shore Waterfront Home, Ready for Spring and Summer!

Fishing Creek house

3 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$222

1 / 9

Deerpond Carriage House

Woolford guest house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$180

1 / 17

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

Cambridge house

7 bedrooms / 7 bathrooms / sleeps 28

“Unbelievable Home in an Unbelievable Setting!!!” Our family cant thank you enough for the memories made at captains quarters this summer. This was the first time getting away with the entire family (kids grandkids, grand parents, etc) and it was prop

Price per night from

$1,000

1 / 35

Cottage at Heron Cove, Chesapeake Bay, Cambridge

Cambridge cottage

3 bedrooms / 1 bathroom / sleeps 5

Price per night from

$166

1 / 50
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