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Leonardtown Holiday Homes

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    $277 Average
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    Don't let other travellers get your favourite Leonardtown area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 19 Rentals in Leonardtown
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    The following rentals are within 30 kilometres of Leonardtown.
    DREAM FAMILY HOUSE ON THE POTOMAC RIVER1 / 20
    (6)Very good
    Montross, VA
    4 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Lusby
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Super Cute, 2 Bedroom, 1 Bath, Furnished Cottage1 / 15
    (7)Average
    Colonial Beach, VA
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    Shannon Point Lodge Peaceful and Private1 / 17
    (45)Excellent
    Kinsale, VA
    4 Bedrooms, 2 Bathrooms, Sleeps 13 Quick View
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    Amenities & Details
    • Porch
    • Internet Access
    • Waterfront
    • DVD Player
    • Washer
    • Grill
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 August 2015
    5 stars are really not enough. Bill and family go above and beyond -- they don't just rent the home (clean linens, kitchen with utensils, cable TVs, Internet, canoe, kayaks...
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    About this property
    Location: Sandy Point, Virginia, USA (2 Hours from Washington D.C., 1.5 Hours from Richmond, Va) Accommodations: House, 4 Bedrooms + Convertible bed(s), 2 Baths (Sleeps 10-12) 2400 Square Feet It was initially built in 1932 as a fishing cottage and was fully renovated in 2008. The Lodge is...
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    Kinsale, Virginia 22488
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 13
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    Cedar Beach Lodge is a Modern Year-Round1 / 8
    (1)Excellent
    Lusby
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Washer
    • Porch
    • Internet Access
    • Grill
    • Parking
    • DVD Player
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cedar Beach Lodge is a modern, smoke free, year-round retreat located in the desirable and private Cove Point Beach Community on the western shore of the Chesapeake Bay. It is conveniently located 1 hour from Annapolis, MD and Washington, DC on Route 4 and 10 minutes from Solomon's Island, MD....
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    Lusby, Calvert County 20657
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    New! 4 BR House on St George Island w/Great Views!1 / 27
    (2)Excellent
    Saint Inigoes
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Satellite TV
    • Patio
    • Internet Access
    • Grill
    • Washer
    • DVD Player
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 June 2017
    Came here for a few days of R&R and left totally relaxed and rejuvenated. We spent most of our time on the front porch as the views were extraordinary, especially the...
    Reviewed 27 May 2017
    less than 2 hours from DC and NOVA, The sunsets are unbelievable! Fullly equipped and stocked kitchen, can sleep 12, all the modern conveniences, a small private beach across a...
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    About this property
    Experience luxury, peace, and tranquility when you stay at this superb 4-bedroom, 2.5-bathroom vacation rental house that sleeps 12 lucky guests on the Potomac River with unrivaled views of Potomac River. Situated on 10 acres of historic wooded land that lines the water, this house ensures amazing...
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    Saint Inigoes, Maryland 20674
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Parker Shores1 / 14
    (28)Very good
    Kinsale, VA
    3 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Grill
    • DVD Player
    • Air Conditioning
    • Washer
    • Waterfront
    • Satellite TV
    • Porch
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 June 2016
    This is a good place. Plenty of sleeping room Three full bedrooms, several sofas downstairs, and a couple of extra cots downstairs. The kitchen was sufficient. The microwave...
    Reviewed 1 June 2016
    The house is located in an amazing location. It has everything you would expect but with a few cons.PROS:* Very cheap.* Great location with a nice deck.* House has...
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    About this property
    Located in Westmoreland County at Sandy Point, VA, in the heart of Virginia's historic Northern Neck, approximately 2 hours from Washington, DC, 1.25 hours from Williamsburg and 1.5 hours from Richmond, VA. This fully furnished waterfront home rests on a protected creek located on the western...
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    Location Information
    Kinsale, Virginia 22488
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 11
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    Stunning Pond House in Coles Point1 / 32
    (1)Excellent
    Coles Point, VA
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Satellite TV
    • DVD Player
    • Parking
    • Air Conditioning
    • Grill
    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 August 2016
    Myself and a few friends ending up spending a enjoyable weekend at this home. I would highly recommend it to anyone looking to get a away from it all for a few days.
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    About this property
    This vacation getaway is on a private lot on a 16 acre pond perfect for canoeing and kayaking, opening to the Potomac River. You are welcome to use our canoe and kayaks during your stay. The house sleeps 10 people in beds, two bedrooms are on the main level (one bedroom with a queen bed and one...
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    Location Information
    Coles Point, Virginia 22469
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    36283 Sunflower Blvd1 / 32
    (1)Excellent
    Piney Point
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PET FRIENDLY* / Sleeps: 10 / View: Community / 3BR, 3BA townhome About this home: This spacious Bayside resort two-story 3-bedroom, 3-bath townhome - at approximately 1,800 square feet - offers just about everything you need for a relaxing vacation on the Delaware Coast. The first...
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    Location Information
    Piney Point, Maryland 19975
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Waterfront Retreat on Monroe Bay-AMAZING SUNSETS!1 / 17
    (6)Excellent
    Colonial Beach, VA
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Satellite TV
    • Washer
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 May 2017
    We were very happy with our choice of a vacation rental.The location is amazing. We were right across the street from the bay. We ate crabs on the deck enjoying the view of the...
    Reviewed 22 December 2016
    I can not say enough about the wonderful vacation we had Sept, 2016. We rented a gulf cart and drove all over!! The location was excellent. The view was amazing! My Husband...
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    About this property
    Marina Sunset is situated on the upper level of a bayfront cottage. 'Incredible' best describes the sunset views of Monroe Bay from the front deck of this gorgeous vacation rental on the 'Point.' This beautifully decorated and fully equipped two-bedroom unit sleeps up to 5 and offers everything...
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    Location Information
    Colonial Beach, Virginia 22443
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Saint Leonard
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Air Conditioning
    • Internet Access
    • Patio
    • Washer
    • Satellite TV
    • Grill
    • Parking
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape your everyday hustle and bustle and discover a hidden treasure right on the Chesapeake Bay sands at this 4-bedroom, 1-bathroom St. Leonard vacation rental cottage. With comfortable accommodations to sleep 8, 1,200 square feet of well-appointed living space and easy access to surrounding...
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    Location Information
    Saint Leonard, Calvert County 20685
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    36486 Wild Rose Circle1 / 45
    (1)Excellent
    Piney Point
    5 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PET FRIENDLY* / 10% Military Discount** / View: Community / Sleeps: 15 / 5BR, 4BA single family home About this home: This spacious 5-bedroom, 4-bath single family home - approximately 3,800 square feet - is a great place to relax and enjoy your vacation. This lovely home sleeps 15...
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    Location Information
    Piney Point, Maryland 19975
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 15
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    Saint Leonard
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Waterfront
    • Internet Access
    • Parking
    • Outdoor Dining Area
    • Air Conditioning
    • DVD Player
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for a peaceful beach getaway? Located in quiet Long Beach overlooking Flag Harbor Yacht Haven marina, this cottage is a few minutes walk to the sandy beach along cliffs famous for fossils from the Miocene. The shallow water is safe for children to swim, and a favorite for fishermen and...
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    Location Information
    Saint Leonard, Calvert County 20685
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Saint Leonard
    1 Bedroom, Sleeps 2 Quick View
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    • Waterfront
    • Outdoor Dining Area
    • Internet Access
    • Grill
    • Patio
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come relax at this charming updated one bedroom bungalow. It overlooks the waters of Wells Cove, a tributary to the Patuxent River which is itself, a tributary to the Chesapeake Bay. This cottage is secluded from the main house, surrounded by water and a wild flower meadow. Somewhat secluded from...
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    Location Information
    Saint Leonard, Calvert County 20685
    Holiday Rental House - 1 Bedroom, Sleeps 2
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    Saint Leonard
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Private Garden
    • Air Conditioning
    • Internet Access
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The "Sweet Spot" on the Bay - this charming 2 BR 1 Bath Cottage with water views is located in a private waterfront community, Long Beach in St. Leonard, MD, just half a block to the beach (which has a nice big shade tree). This cozy little cottage is super comfy and fully furnished with linens...
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    Location Information
    Saint Leonard, Calvert County 20685
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Colonial Beach, VA
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Grill
    • Satellite TV
    • Washer
    • Air Conditioning
    • DVD Player
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take leisure to the next level on your upcoming coastal retreat by reserving 'The Blue Crab Cottage,' a traditional bungalow-style Colonial Beach vacation rental home. Supremely located just 2 blocks from the glorious beach and only 4 blocks away from downtown amenities such as municipal halls,...
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    Location Information
    Colonial Beach, Virginia 22443
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Piney Point
    5 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View:  Lake  / Sleeps:  15 /  5BR , 4BA single family home About this home:   Just built & just listed for 2017 rentals! Be one of the first to vacation in "Anchors Aweigh!" In The Shoals - Bayside resort's newest area, this two-story 5-bedroom, 4-bath coastal single family...
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    Location Information
    Piney Point, Maryland 19975
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 15
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    Piney Point
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View:  Pond  / Sleeps:  14 /  5BR , 4BA single family home About this home:   Just built & just listed for 2017 rentals! Be one of the first to experience this upscale, beachy two-story 5-bedroom, 4-bath coastal single family vacation home, located in the exceptionally-amenitied...
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    Location Information
    Piney Point, Maryland 19975
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    Kinsale, VA
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Parking
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tween is located at Sandy Point, Virginia on the Northern Neck. The house is on the waterfront of the Potomac River where it is approximately five miles across to the Maryland shores. You look out onto the Chesapeake Bay from the porch. The beach is sand and the water has a gradual depth increase -...
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    Location Information
    Kinsale, Virginia 22488
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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