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Holiday Rentals in Saint Leonard, MD

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    ₹ 21,339 Average
    ₹ 68,000+
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    Saint Leonard
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    The following rentals are within 40 kilometres of Saint Leonard, Calvert County, Maryland.

    1 / 7
    5 of 5 stars (9) Excellent
    Bozman, MD
    4 Bedrooms, 3 Bathrooms, Sleeps 13 | Quick View
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    1 / 9
    5 of 5 stars (1) Excellent
    Bozman, MD
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 22
    5 of 5 stars (6) Excellent
    Cambridge, MD
    7 Bedrooms, 6 Bathrooms, Sleeps 28 | Quick View
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    Amenities & Details
    • Private Outdoor...
    • Waterfront
    • Hot Tub
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Experience the lavish surroundings of Captain's Quarters. Whether your pleasure is sailing, fishing, water sports, relaxing by the pool and jacuzzi or nestling up on the veranda with a good book, Captain's Quarter's provides luxury around every corner. This unrivaled waterfront estate accommodates... View all property information
    Location Information
    Cambridge, Maryland 21613
    4 of 5 stars Reviewed 3 weeks ago
    Lovely setting & a great location for sure. Nice big comfortable house. Great spot for big family reunion. This was our 2nd time we stayed here. Loved our first visit a couple...
    5 of 5 stars Reviewed 3 August 2012
    I would not change a single thing. Our family enjoyed the six day stay at this awesome place. The amenities were great, the location was central to other sights, and the...
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    Saint Mary's City, MD
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Wi-Fi
    • DVD Player
    • Parking
    • Satellite TV
    • Grill
    • Washer
    • Air Conditioning
    • Ocean Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    This immaculate, fully renovated Cottage with comfortable interior and nice woodland views has a cozy CENTRAL HEAT. An electric fireplaces in the Dinning room offers ambience as does the glow of the battery run candles in the den's fireplace. If you are in to burning wood there is a fire pit with a... View all property information
    Location Information
    Saint Mary's City, Maryland 20690
    1 / 12
    Deale, MD
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Waterfront
    • DVD Player
    • Grill
    • Air Conditioning
    • Balcony
    • Porch
    • Satellite TV
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    About this property
    Fredelig sted'(peaceful place) is patterned after a Norwegian cottage with curved roof on the outside and knotty pine and birch wood inside. The bright panoramic view of the Chesapeake from the great room, master bedroom or deck elicits a relaxed, peaceful mood as soon as you arrive. Watch the... View all property information
    Location Information
    Deale, Maryland 20751
    Neavitt, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Patio
    • Wi-Fi
    • Waterfront
    • Washer
    • Grill
    • Parking
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    About this property
    Newly renovated cottage in the village of Neavitt. Neavitt is a great village only 10 minutes away from St. Michaels. The house has waterviews and access to it's own personal dock which is great for fishing, kayaking or paddle boarding. Spend the day out on local waterways and then relax the night... View all property information
    Location Information
    Neavitt, Talbot County 21652
    1 / 34
    Piney Point, MD
    3 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    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
    Location Information
    Piney Point, Maryland 19975
    1 / 8
    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
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
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    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
    Location Information
    Lusby, Calvert County 20657
    Cambridge, MD
    6 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • Wi-Fi
    • Balcony
    • Air Conditioning
    • Washer
    • Terrace
    • Parking
    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    About this property
    Located on the beautiful Eastern Shore of Maryland, Cambridge has been named one of the best ten small towns in the U.S. and is a boater's dream! The house has four private suites, full gourmet kitchen, three sitting areas, and two car garage. Check out the Dorchester County Tourism page for... View all property information
    Location Information
    Cambridge, Maryland 21613
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    Woolford, MD
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Private Garden
    • Satellite TV
    • Wi-Fi
    • Secure Parking
    • Air Conditioning
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    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... View all property information
    Location Information
    Woolford, Maryland 21677
    1 / 20
    5 of 5 stars (2) Excellent
    Fishing Creek, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Washer
    • Air Conditioning
    • Satellite TV
    • Waterfront
    • Housekeeping...
    • Ocean Views
    • Grill
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
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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!!! April thru October on Hooper's Island is must do on your... View all property information
    Location Information
    Fishing Creek, Maryland 21634
    5 of 5 stars Reviewed 26 September 2015
    We came to Hoopers Island looking for three days of tranquility, and that is exactly what we found. The house is beautiful and was a great place to stay. The pool table was an...
    5 of 5 stars Reviewed 16 September 2015
    Best Kept Secret by the Bay is just that! The house was as described and pictured and equipped with everything we needed during our stay there 8/31/15-9/7/15. The house looked...
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    1 / 20
    5 of 5 stars (5) Excellent
    Tilghman, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • DVD Player
    • Satellite TV
    • Parking
    • Air Conditioning
    • Waterfront
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
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    About this property
    Enjoy the beauty and tranquility of Tilghman Island from this bright and comfortable 3 bedroom, 2 bathroom cottage known for many years as the vacation rental 'The Roost.' Available for both short and long-term rentals, the cottage is located on a quiet residential street across from a marina... View all property information
    Location Information
    Tilghman, Talbot County 21671
    5 of 5 stars Reviewed 8 October 2015
    Tilghman Cottage (the Roost) is a lovely place that makes you feel comfortable in every possible way. The house is very clean, bright, cosy, and yet spacious, fully equipped with...
    5 of 5 stars Reviewed 4 June 2015
    This is a delightful place to stay with lots to see and do in the area, from the Maritime Museum in St. Michaels, to Cambridge, to the Ward Museum In Salisbury. We anticipated...
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    Lusby
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Porch
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Grill
    • DVD Player
    • Children's Pool
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • 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
    Location Information
    Lusby, Calvert County 20657
    1 / 30
    4.5 of 5 stars (11) Very good
    Cambridge, MD
    6 Bedrooms, 5 Bathrooms, Sleeps 16 | Quick View
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    • Air Conditioning
    • Waterfront
    • Hot Tub
    • Satellite TV
    • Internet Access
    • Sauna
    • Private Outdoor...
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    About this property
    Fabulous, recently-built premier vacation home on 500 feet of Chesapeake waterfront. A gorgeous home; beach, dock, private pool, boats, bikes, porches & mile-wide view With 6 acres of property, wide water & sandy beaches, this private luxury vacation rental is minutes from Cambridge,... View all property information
    Location Information
    Cambridge, Maryland 21677
    4 of 5 stars Reviewed 1 April 2014
    We had a group of 9 women stay here for a crafting weekend. The house was perfect for us. We brought a few folding tables and were able to all be in the large open rooms together...
    3 of 5 stars Reviewed 28 July 2013
    Our family spent a week at Saddle Beach House on the Eastern Shore over 4th of July. Unfortunately it was not the vacation we were hoping for. We chose this property because of...
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    1 / 26
    5 of 5 stars (1) Excellent
    Cobb Island, MD
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Washer
    • Grill
    • Parking
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
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    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
    Location Information
    Cobb Island, Maryland 20625
    Coles Point, VA
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
    • Washer
    • Balcony
    • Terrace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    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. Coles Point is nearby to historic Montross, Tappahanock, Kilmarnock, and many more of the Northern Neck's charming historical towns. The Northern Neck is home to civil war... View all property information
    Location Information
    Coles Point, Virginia 22469
    1 / 24
    5 of 5 stars (1) Excellent
    Churchton, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
    • Satellite TV
    • Washer
    • Grill
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    This sunny but cozy 3 bedroom/2 bath cottage is just the spot for a get-away on your own, with other couples/friends, or with big and small familie! Just steps from the water and nestled on a country-like acre in a surprisingly convenient corner of the Chesapeake Bay, this unique, quiet, scenic... View all property information
    Location Information
    Churchton, Maryland 20733
    5 of 5 stars Reviewed 1 week ago
    Stayed a few days in the cottage...there is another quarters for a couple next door at the main house ,and another room they are renting and working on expanding I...
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    1 / 17
    4.5 of 5 stars (5) Very good
    North Beach
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    • DVD Player
    • Waterfront
    • Satellite TV
    • Air Conditioning
    • Grill
    • Washer
    • Wi-Fi
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    The Seahorse Guest Cottage is located in North Beach, Maryland, on the western shore of the Chesapeake Bay, within an hour’s drive of Washington, Baltimore, and Annapolis. The fully furnished cottage has a living room with sofabed, bedroom with queen size bed, sunporch with day bed, a full... View all property information
    Location Information
    North Beach, Calvert County 20714
    5 of 5 stars Reviewed 15 November 2014
    Just as described- walk to boardwalk and shops. Owner right next door, he's thought of everything. Lovely getaway destination.
    5 of 5 stars Reviewed 8 July 2013
    We absolutely fell in love with this quiet little cabin a block away from Chesapeake Bay. Gary, the owner, met us at the cabin and personally gave us a tour of the cabin and let...
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    1 / 39
    Cambridge, MD
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Porch
    • DVD Player
    • Parking
    • Waterfront
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    About this property
    The Cottage at Heron Cove is a cozy home situated on a scenic peninsula with water views from every window. Awake each morning to watch the sun glisten off the gentle waters. Explore ten acres of land and 1000 feet of shoreline. Relax on the wrap around screened in porch. Fish and crab from your... View all property information
    Location Information
    Cambridge, Maryland 21613
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    Deale, MD
    2 Bedrooms, 7 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Housekeeping...
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Sauna
    • Parking
    • Shared Garden
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    About this property
    Enjoy the home and studio of local sculptor artist. This apartment includes the second and third floors, approximately 2,300 sf of space. Large and comfortable bedrooms, large bathrooms, showers have double heads, sauna in the main master-bath. We provide linens and towels. This apartment has a... View all property information
    Location Information
    Deale, Maryland 20751
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    5 of 5 stars (1) Excellent
    Piney Point, MD
    5 Bedrooms, 5 Bathrooms, Sleeps 15 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    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
    Location Information
    Piney Point, Maryland 19975
    1 / 18
    4 of 5 stars (10) Very good
    Cambridge, MD
    6 Bedrooms, 3 Bathrooms, Sleeps 18 | Quick View
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    • Air Conditioning
    • Satellite TV
    • Patio
    • Waterfront
    • Washer
    • Grill
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    About this property
    The Swan's Nest in Cambridge, Maryland, has all that the Chesapeake Bay has to offer: sun, sand, fishing, crabbing,and so much more. The spacious and lovingly restored farmhouse can accommodate 18 guests. The kitchen is fully equipped and a barbeque pit is just outside on the patio. Bring your... View all property information
    Location Information
    Cambridge, Maryland 21613
    5 of 5 stars Reviewed 22 August 2015
    We arrived to find the owners on the property, eager to give us a tour and ensure we had everything we needed. The home was clean, comfortable, and had everything we needed! Our...
    4 of 5 stars Reviewed 20 August 2015
    Our family of 15 with children ranging from 2 months to 6 years had a wonderful vacation at Swans Nest!! The large roomy farmhouse was very accommodating. Kitchen very well...
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    1 / 5
    3 of 5 stars (1) Average
    Cambridge, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    About this property
    Charming, historic home in the Neck District, Maryland's most beautiful, unspoiled area. This adorable east-facing 100-year-old home sits on a generous lot (over an acre) with forever waterviews, mature shade trees, flowering perennials, roses, large fenced vegetable garden, breezy patio, wide... View all property information
    Location Information
    Cambridge, Maryland 21613
    Clements, MD
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • Parking
    • Wi-Fi
    • Terrace
    • Washer
    • Shared Garden
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • 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
    Location Information
    Clements, Maryland 35800
    1 / 42
    5 of 5 stars (2) Excellent
    Cambridge, MD
    5 Bedrooms, 4 Bathrooms, Sleeps 18 | Quick View
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    • Air Conditioning
    • Internet Access
    • DVD Player
    • Washer
    • Satellite TV
    • Grill
    • Waterfront
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
    • x
    About this property
    Swan Cove awaits your family vacation or group! It's also an ideal place for a most memorable wedding. This incredible, newly redesigned waterfront home with a private dock offers spectacular views with a large swimming pool, 4 kayaks, outdoor firepit (firewood is furnished), playground and a large... View all property information
    Location Information
    Cambridge, Maryland 21613
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    Piney Point, MD
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • 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
    Location Information
    Piney Point, Maryland 19975
    North Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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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... View all property information
    Location Information
    North Beach, Calvert County 20714
    Tracys Landing, MD
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Air Conditioning
    • Sauna
    • Hot Tub
    • Waterfront
    • Wi-Fi
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • Smoking allowed
    • Elder access
    • x
    About this property
    The Bay Breeze Lodge is your weekend escape, to relax, watching the panoramic waterfront views of the Chesapeake Bay in every room. Fish, crab, on private pier. Family friendly, new construction home. A short drive from the city, yet a world away. Beach 2min- steam room - fireplace- beach modern... View all property information
    Location Information
    Tracys Landing, Maryland 20779
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    Lusby
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Internet Access
    • Parking
    • Air Conditioning
    • Washer
    • Satellite TV
    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
    • x
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    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
    Location Information
    Lusby, Calvert County 20657