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Vacation Rentals in Leonardtown, MD and nearby

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    The following rentals are within 20 miles of Leonardtown, Maryland.

    From
    $400
    / Night
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    Lusby
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    other travelers have booked this property
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    From
    $125
    / Night
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    1 / 17
    5 of 5 stars (3) Excellent
    Colonial Beach, VA
    2 Bedrooms, 1 Bathroom, Sleeps 4
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    Overview Reviews (3)
    From
    $150
    / Night
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    1 / 13
    5 of 5 stars (10) Excellent
    Montross, VA
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    other travelers have booked this property
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    Overview Reviews (10)
    From
    $150
    / Night
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    Saint Mary's City
    3 Bedrooms, 1 Bathroom, Sleeps 6
    other travelers have booked this property
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Wi-Fi
    • Private Fishing...
    • Water Views
    • Children's Pool
    • Satellite TV
    • Ocean Views
    • Housekeeping...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Fifteen miles by land from St. Mary's City is where you will find Tall Timbers Cottage only two hours from the District of Columbia. along the shore of the Potomac River. You will find our immaculate, fully renovated Cottage with comfortable interior and nice woodland views with cozy central heat,... View all property information
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    Location Information
    Saint Mary's City, Maryland 20690
    From
    $125
    / Night
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    1 / 15
    4 of 5 stars (1) Very good
    Colonial Beach, VA
    2 Bedrooms, 1 Bathroom, Sleeps 3
    other travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • DVD Player
    • Stereo System
    • Dryer
    • Air Conditioning
    • Patio
    • Washer
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Super cute, furnished cottage on the point. 2 bedroom, 1 bath, kitchen, sunroom, covered back patio. Renovated bathroom, hardwood floors, fenced yard. Come relax and enjoy a sunset walk around the point. Nestled on a quiet street two blocks from the Potomac River and two blocks from Monroe Bay.... View all property information
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    Location Information
    Colonial Beach, Virginia 22443
    4 of 5 stars Reviewed September 30, 2013
    The cottage was nice and perfect size for our family of three - they were able to accomodate us and our family dog on very short notice and we enjoyed our 2 night stay.
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    From
    $400
    / Night
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    1 / 26
    5 of 5 stars (1) Excellent
    Cobb Island
    4 Bedrooms, 2 Bathrooms, Sleeps 9
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • DVD Player
    • Stereo System
    • Boat Available
    • Internet Access
    • Water Views
    • Air Conditioning
    • Waterfront
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Welcome to our Cobb Island, Maryland Home, on the waterfront in Southern Maryland, one hour from Washington D.C. - the perfect spot to spend your next relaxed family vacation enjoying water oriented activities and fabulous river views. We have been renting this house to more than 200 families... View all property information
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    Location Information
    Cobb Island, Maryland 20625
    From
    $260
    / Night
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    Saint Leonard
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    other travelers have booked this property
    Overview Make Inquiry
    Overview
    Amenities & Details
    • DVD Player
    • Waterfront
    • Internet Access
    • Stereo System
    • Deck
    • Air Conditioning
    • Water Views
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    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... View all property information
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    Location Information
    Saint Leonard, Calvert County 20685
    From
    $261
    / Night
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    1 / 29
    5 of 5 stars (1) Excellent
    Piney Point
    5 Bedrooms, 4 Bathrooms, Sleeps 15
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
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    Location Information
    Piney Point, Maryland 19975
    5 of 5 stars Reviewed June 28, 2015
    Great house. Lots of space and beds. A terrific rental. Well worth the $$. Bayside is a wonderful resort community. Pools, paddle boarding, golf, tennis -- it has it all.
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    From
    $140
    / Night
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    1 / 43
    Piney Point
    3 Bedrooms, 3 Bathrooms, Sleeps 10
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    PET FRIENDLY* / Sleeps: 10 / View: Community / 3BR, 3BA townhome About this home: You will enjoy amazing ambiance at Aurora Cottage as you enter the great room living area with 20-foot ceilings, 2 tropical ceiling fans, and seating for viewing the fireplace or HDTV. Many creature... View all property information
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    Location Information
    Piney Point, Maryland 19975
    From
    $149
    / Night
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    Colonial Beach, VA
    3 Bedrooms, 3 Bathrooms, Sleeps 5
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Refrigerator
    • Stove
    • Satellite TV
    • Dryer
    • Wi-Fi
    • Water Views
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Clean and Comfortable 3 bedroom/2 bath Furnished home located in the heart of Colonial Beach, VA Offers both relaxation and comfort with all new furnishing as of August 2015. Plush Sectional Sofa, pillow top matresses, cable TV, internet access, Jacuzzi tub. Washer and dryer in laundry area. Walk... View all property information
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    Location Information
    Colonial Beach, Virginia 22443
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    From
    $165
    / Night
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    Hague, VA
    2 Bedrooms, 1 Bathroom, Sleeps 5
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Stereo System
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Washer
    • Watersports Nearby
    • Dryer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The Cottage at the Hague Winery - Original Homestead dating back to the 1800's The renovated cottage features full kitchen, satellite TV, Wi-Fi, central air and all the comforts of home in an historic cottage situated in the midst of rolling farm land and only a short walk across the lawn to The... View all property information
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    Location Information
    Hague, Virginia 22469
    From
    $300
    / Night
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    Montross, VA
    4 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Make Inquiry
    Overview
    Amenities & Details
    • DVD Player
    • Stereo System
    • Waterfront
    • Air Conditioning
    • Private Fishing...
    • Ocean Views
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Experience a home where views are breathtaking, the breeze refreshing, the daily eagle sightings amazing! Kids love playing in the fields or splashing in the water. The resident frog keeping watch over his pool and may sing for you at night night. Take family trips in the canoe and kayaks or go... View all property information
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    Location Information
    Montross, Virginia 22520
    From
    $112
    / Night
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    Clements
    4 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Balcony
    • Refrigerator
    • Washer
    • Garage
    • Internet Access
    • Stove
    • Parking
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Holiday House Rental in Dinard, Britany, France This house is 15 minutes far on foot from the beach. This well decorated house has place for 8 persons. This invite you to discover the 'Pink Granite Coast' and attractions: Saint-Malo (10 km), the historical oldtown from Dinan. A 45 minute drive... View all property information
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    Location Information
    Clements, Maryland 35800
    From
    $180
    / Night
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    1 / 24
    Piney Point
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Inquiry
    Overview
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    PET FRIENDLY* / Sleeps: 4 / View: Community / 2BR, 2BA townhome About this home: This Bayside resort 2-bedroom, 2-bath townhome has just about everything you need for a relaxing vacation. This home features a tastefully-decorated family room, dining area, kitchen and a spacious... View all property information
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    Location Information
    Piney Point, Maryland 19975
    From
    $120
    / Night
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    1 / 11
    Lusby
    2 Bedrooms, 1 Bathroom, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Internet Access
    • Fireplace
    • Air Conditioning
    • Stereo System
    • Deck
    • Satellite TV
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Lovely year round rental cottage situated on almost one acre within a few minutes walk to one of the longest private beaches on the western shore of the Chesapeake Bay. Enjoy walking the mile beach to the historic Cove Point Lighthouse collecting sea shells or hunting for fossils, especially... View all property information
    Make Inquiry
    Location Information
    Lusby, Calvert County 20657
    From
    $300
    / Night
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    1 / 8
    Lusby
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Air Conditioning
    • Stereo System
    • Fireplace
    • Internet Access
    • Deck
    • Washer
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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.... View all property information
    Make Inquiry
    Location Information
    Lusby, Calvert County 20657
    From
    $100
    / Night
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    1 / 17
    5 of 5 stars (1) Excellent
    Kinsale, VA
    4 Bedrooms, 2 Bathrooms, Sleeps 13
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Washer
    • Internet Access
    • Waterfront
    • DVD Player
    • Stereo System
    • Deck
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
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    Location Information
    Kinsale, Virginia 22488
    5 of 5 stars Reviewed August 27, 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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    From
    $300
    / Night
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    1 / 8
    Lusby
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Fireplace
    • Washer
    • Internet Access
    • Deck
    • Stereo System
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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.... View all property information
    Make Inquiry
    Location Information
    Lusby, Calvert County 20657
    From
    $100
    / Night
    View Details
    1 / 14
    Kinsale, VA
    3 Bedrooms, 2 Bathrooms, Sleeps 11
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Stereo System
    • Internet Access
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Fireplace
    • Boat Available
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
    Make Inquiry
    Location Information
    Kinsale, Virginia 22488
    From
    $100
    / Night
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    1 / 14
    5 of 5 stars (1) Excellent
    Kinsale, VA
    3 Bedrooms, 2 Bathrooms, Sleeps 11
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Boat Available
    • DVD Player
    • Internet Access
    • Stereo System
    • Waterfront
    • Satellite TV
    • Fireplace
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
    Make Inquiry
    Location Information
    Kinsale, Virginia 22488
    5 of 5 stars Reviewed January 27, 2015
    Excellent location, lots to do even in the dead of winter. Owner was readily accessible and promptly responded to our requests.
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    From
    $104
    / Night
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    1 / 26
    5 of 5 stars (1) Excellent
    Colonial Beach, VA
    3 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Washer
    • Stereo System
    • Waterfront
    • Dryer
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Main house has two bedrooms and two baths, full kitchen, laundry, hide-away bed in living room. Guest house in back with full bath and two beds. Private 130+ foot deep water pier extends into the Potomac River. Enjoy fishing from private pier or bring your boat. Two marinas nearby provide boat... View all property information
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    Location Information
    Colonial Beach, Virginia 22443
    5 of 5 stars Reviewed September 22, 2014
    Great cottage. Beautiful waterfront views. Loved watching the sunrises over the water and the private dock. Cottage well equipped. owner very accomodating.
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    From
    $120
    / Night
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    1 / 11
    Lusby
    2 Bedrooms, 1 Bathroom, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Stereo System
    • Satellite TV
    • DVD Player
    • Internet Access
    • Deck
    • Washer
    • Air Conditioning
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Lovely year round rental cottage situated on almost one acre within a few minutes walk to one of the longest private beaches on the western shore of the Chesapeake Bay. Enjoy walking the mile beach to the historic Cove Point Lighthouse collecting sea shells or hunting for fossils, especially... View all property information
    Make Inquiry
    Location Information
    Lusby, Calvert County 20657
    From
    $104
    / Night
    View Details
    1 / 26
    Colonial Beach, VA
    3 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Satellite TV
    • DVD Player
    • Internet Access
    • Stereo System
    • Washer
    • Air Conditioning
    • Waterfront
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Main house has two bedrooms and two baths, full kitchen, laundry, hide-away bed in living room. Guest house in back with full bath and two beds. Private 130+ foot deep water pier extends into the Potomac River. Enjoy fishing from private pier or bring your boat. Two marinas nearby provide boat... View all property information
    Make Inquiry
    Location Information
    Colonial Beach, Virginia 22443
    From
    $100
    / Night
    View Details
    1 / 17
    Kinsale, VA
    4 Bedrooms, 2 Bathrooms, Sleeps 13
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Deck
    • Air Conditioning
    • Washer
    • DVD Player
    • Stereo System
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
    Make Inquiry
    Location Information
    Kinsale, Virginia 22488