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Saint Leonard Holiday Homes

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    Don't let other travellers get your favourite Saint Leonard area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 20 Rentals in Saint Leonard
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    Saint Leonard
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Spring Is Here, Come Explore Fossils and One Mile of Beach1 / 42
    (2)Very good
    Saint Leonard
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Saint Leonard
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    RELISTED!! Chesa. Bay Vacation Rental, quiet, beachy, open, bay view!1 / 23
    (35)Excellent
    Saint Leonard
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Patio
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    Saint Leonard, Calvert County 20685
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Chesapeake Bay Beach Cottage - The Sweet Spot on the Bay!1 / 32
    (14)Excellent
    Saint Leonard
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Saint Leonard, Calvert County 20685
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    The following rentals are within 30 kilometres of Saint Leonard.
    Best kept secret by the bay (Entire House)1 / 20
    (4)Excellent
    Fishing Creek, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • Housekeeping Included
    • Ocean Views
    • Washer
    • Wi-Fi
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    Pet friendly
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    Reviewed 4 October 2016
    This rental property was amazing. My husband and I stayed for 5 days. We were in town for the Ironman race and wanted to find somewhere a bit away from all the crowds. Hoopers...
    Reviewed 20 June 2016
    This beautiful home offers everything, and more, one could ask for in a vacation rental. The view of the water is spectacular and we were able to enjoy those views in the...
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    About this property
    Hooper's Island is located between the Honga River and Chesapeake Bay on Marylands Eastern Shore. This unique island is a 'MUST DO' on your bucket list. Especially noted for: Maryland's famous Blue Crabs and Breathtaking Sunsets!!! Hooper's Island is must do on your bucket list as you...
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    Fishing Creek, Maryland 21634
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
    Chesapeake Bay Waterfront on Hoopers Island with Private Beach1 / 35
    (3)Very good
    Fishing Creek, MD
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Reviewed 24 September 2019
    Enjoyed this property as a place to reconnect with old friends. Enjoyed views of the bay from the porch, stargazing, biking, walks. Small private beach. Old Salty’s next...
    Reviewed 3 October 2018
    Jerry is a wonderful host and was flexible with our check-in time. The house was spotless when we arrived, and the kitchen and cookware was well stocked. The house resides a few...
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    About this property
    This lovely home offers all the comforts of home, including a covered porch where you can meditate, read, paint, bird watch and get away from it all, as the quiet natural beauty of the area makes it the perfect retreat! The house features spectacular views of the bay and sunsets from the first...
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    Fishing Creek, Maryland 21634
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Hoopers Island Studio, 360 Degrees WATER VIEWS near IRONMAN Cambridge1 / 38
    (4)Excellent
    Fishing Creek, MD
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Patio
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    Pet friendly
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    Smoking allowed
    Reviewed 31 October 2018
    This place was truly breathtaking. The drive from Cambridge, alone, is worth the trip. I was competing in an Ironman triathlon, and this place was easily one of the best finds...
    Reviewed 17 January 2018
    Memories of the peace, beauty and comfort of Fishing Creek, Maryland and of the sparkling, colorful Queen Anne Cottage that is Hoopers Island Haven warm my cold winter days! If...
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    About this property
    360 Degree Views, WATERFRONT and Waterback, TWO DOCKS Scenic, peaceful and spacious studio apartment located on the entire second floor of our property. Open April to Nov. 15, AVAILABLE FOR 2 NIGHT STAY MINIMUM, sorry NO EXCEPTIONS 3rd person $25 extra per night...
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    Fishing Creek, Maryland 21634
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    North Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    About this property
    All-Decked-Out Beach House is on the Western Shore of the Chesapeake Bay in the lovely Rose Haven/North Beach MD community. Fenced-in on a large corner lot directly across from Herrington on the Bay, 3 miles from Chesapeake Beach Bay Resort & Spa and 45 min. from DC this 3bed/1.5 bath offers...
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    North Beach, Calvert County 20714
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Fishing Creek, MD
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious Historic Home. Wide open water views on both sides of the house! Come to discover 'Hoopers Hill'. Relax between waterfront sunrise and waterfront sunset. Gourmet kitchen, private beach, starry evening skies, and quiet reading spaces await. Shoreline crabbing, oystering and fishing too....
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    Fishing Creek, Maryland 21634
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    North Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    This charming restored cottage has all the luxury upgrades you could want!! Gourmet kitchen with granite counters and double-oven, 5-burner gas cooktop, and plenty of storage. Easy-to-enjoy gas fireplace, and ample space for entertaining and kids to play -- both indoors and out! Convenient to...
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    North Beach, Calvert County 20714
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Chesapeake Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    This ground floor 1-bedroom, 1-bath Chesapeake Bay vacation rental is perfect for a couples retreat. The newly renovated property is outfitted with everything you need to let your worries melt away under the Maryland sun including beach chairs, sun umbrellas, charcoal grill, in-unit laundry...
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    Chesapeake Beach, Calvert County 20732
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Woolford, MD
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Garden
    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Quiet Waterfront Retreat in Estate Setting - You will be staying in a charming, waterfront, 1-bedroom, carriage house located on a five-acre estate with surrounding tall pines and stately cedars. Your living quarters on the second floor, with private entrance and balcony, will overlook the pool and...
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    Location Information
    Woolford, Maryland 21677
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Chesapeake Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    • Shared Indoor Pool
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Contemporary all-brick French manor nestled within 16-acres of secluded woodlands. Indoor pool/spa with waterfall inside a stunning, sunlit atrium. Three bedrooms and three bathrooms accommodate 6-8 people. Centrally located near the Chesapeake Bay where quaint towns include restaurants, antiques,...
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    Chesapeake Beach, Calvert County 20732
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Broomes Island
    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Patio
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    • Central Heating
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    Pet friendly
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    About this property
    The Mackall House is a spacious fully-remodeled six bedroom home with two master suites, five full baths, and two half baths! There are two full kitchens, a huge common area, and a large game room downstairs. The game room includes a pool table, foosball table and a shuffleboard table! This is the...
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    Broomes Island, Calvert County 20685
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
    North Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Just 3 blocks from the board walk and beach, 2 blocks from the restaurants! Newly Renovated Crystal Cove Retreat! Your Relaxation Beach Spot Destination. Modern luxury home, each room has a different crystal for you to meditate with. Kick back and relax in one of the recliners as you watch your...
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    North Beach, Calvert County 20714
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Fishing Creek, MD
    7 Bedrooms, 3 Bathrooms, Sleeps 17 Quick View
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    • Terrace
    • Balcony
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The historic Queen Anne Victorian vacation rental home is the perfect, quiet respite for friends and family. With 7 bedrooms, 2.5 baths, and views of the Chesapeake Bay from almost every window, this scenic home is perfect for up to 17 guests looking to getaway. Updates and amenities provide...
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    Fishing Creek, Maryland 21634
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 17
    Lusby
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Are you traveling for business or just for vacation? If so my one bedroom in-law suite w/ a large walk in closet, spacious living room, one full bathroom w/ access to a washer/dryer should be a perfect fit. For vacation 15-20mins from local waterfront restaurants/bars. Local attractions include...
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    Lusby, Calvert County 20657
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Lusby
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Terrace
    • Balcony
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Secluded location for those who like nature and view of water through the trees. Loft with twin beds and a sofa bed in main living area. Furnished and equipped for short stays especially close to Cove Point, Calvert Cliffs and across the river from PAX Naval Air station. Share property with owners,...
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    Lusby, Calvert County 20657
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Tilghman, MD
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take the scenic route from Washington D.C. all the way to this Tilghman Island home for a restorative week of sailing, fishing, and fine dining! See Lady Patty Classic Yacht Charters 2 miles away and peruse the Chesapeake Bay coastline in style, then visit the nearby winery at St. Michaels less...
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    Location Information
    Tilghman, Talbot County 21671
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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