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Vacation Rentals in Saint Leonard, MD and nearby

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    1 / 10
    Saint Leonard
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 13
    Saint Leonard
    1 Bedroom, Sleeps 2 | Quick View
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    1 / 17
    Saint Leonard
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 18
    Saint Leonard
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
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    • x
    Location Information
    Saint Leonard, Calvert County 20685

    The following rentals are within 25 miles of Saint Leonard, Calvert County, Maryland.

    1 / 32
    5 of 5 bubbles (1) Excellent
    Coles Point, VA
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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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... View all property information
    Location Information
    Coles Point, Virginia 22469
    5 of 5 bubbles Reviewed August 15, 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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    1 / 20
    5 of 5 bubbles (4) Excellent
    Fishing Creek, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Ocean Views
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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... View all property information
    Location Information
    Fishing Creek, Maryland 21634
    5 of 5 bubbles Reviewed October 3, 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...
    5 of 5 bubbles Reviewed June 20, 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 comfort...
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    1 / 11
    Neavitt, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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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 / 26
    Saint Mary's City, MD
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
    About this property
    This property is Perfect for the spring months, our fully renovated cottage with clean and cozy interior has a stunning views from the grounds overlooking the Potomac River. We love to spot the night lights of Virginia, the spectacular sunset views, and abundance of wildlife. A water access... View all property information
    Location Information
    Saint Mary's City, Maryland 20690
    1 / 29
    Lusby
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Porch
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    • Children's Pool
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    • Pet-friendly
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    • 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 / 8
    Lusby
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • ?
    • Smoking allowed
    • 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
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    1 / 38
    5 of 5 bubbles (2) Excellent
    Fishing Creek, MD
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    360 Degree Views, WATERFRONT Scenic, peaceful and spacious studio apartment located on the entire second floor of our property. AVAILABLE FOR 3 NIGHT STAY MINIMUM, sorry NO EXCEPTIONS 3rd person $50 extra per stay Ironman/Eagleman/Event/Holiday $75 extra per stay Discounted weekly rates.... View all property information
    Location Information
    Fishing Creek, Maryland 21634
    5 of 5 bubbles Reviewed August 12, 2014
    We came to this historic area to do some fishing. The house was well equipped with emphasis to detail. A great deal of creativity is evident once you step inside. You find...
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    1 / 20
    5 of 5 bubbles (6) Excellent
    Tilghman, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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 bubbles Reviewed July 21, 2016
    We had an absolutely wonderful time. The cottage was clean and well appointed. We would definitely go back!
    5 of 5 bubbles Reviewed October 8, 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...
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    1 / 17
    4.5 of 5 bubbles (5) Very good
    North Beach
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    • x
    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 bubbles Reviewed November 15, 2014
    Just as described- walk to boardwalk and shops. Owner right next door, he's thought of everything. Lovely getaway destination.
    5 of 5 bubbles Reviewed July 8, 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 / 24
    5 of 5 bubbles (1) Excellent
    Churchton, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • ?
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    • x
    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 bubbles Reviewed May 14, 2016
    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 / 9
    Fishing Creek, MD
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • x
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    • x
    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.... View all property information
    Location Information
    Fishing Creek, Maryland 21634
    1 / 32
    5 of 5 bubbles (1) Excellent
    Piney Point, MD
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    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... View all property information
    Location Information
    Piney Point, Maryland 19975
    1 / 39
    Cambridge, MD
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Porch
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    • Pet-friendly
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    • x
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    • x
    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
    1 / 18
    Neavitt, MD
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Waterfront
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    • Patio
    • Balcony
    • DVD Player
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Full renovations just completed on this newly-listed historic waterfront home. Sleeps five (1 King, 1 Queen, 1 Twin). Kick back, relax and enjoy the beautiful waterviews. Have crabs on the deck or cocktails on the dock. Features a new dock with 14 ft. and 16 ft. wide, deepwater boat slips. Bring... View all property information
    Location Information
    Neavitt, Talbot County 21652
    1 / 20
    Deale, MD
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Sauna
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    • x
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    • x
    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
    1 / 45
    5 of 5 bubbles (1) Excellent
    Piney Point, MD
    5 Bedrooms, 4 Bathrooms, Sleeps 15 | Quick View
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    • Internet Access
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    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
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    1 / 20
    5 of 5 bubbles (2) Excellent
    Cambridge, MD
    8 Bedrooms, 6 Bathrooms, Sleeps 23 | Quick View
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    • Washer
    • Terrace
    • Waterfront
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    • Central Heating
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    Fishing cove is an 8 bedroom, 6 bath waterfront house tucked away in a lush pine forest that we rent on a monthly, weekly or weekend basis. Our waterfront vacation rental home on Maryland's Eastern Shore is on a very private cove with its own pier. The house is wheelchair accessible and the main... View all property information
    Location Information
    Cambridge, Maryland 21613
    5 of 5 bubbles Reviewed December 13, 2016
    We had 14 people for thanksgiving..house had everything we needed! The kitchen was fully stocked with all the necessary cooking implements. And the 2 refrigerators were very...
    5 of 5 bubbles Reviewed December 5, 2016
    Our church group (11 men of all ages) had a most excellent weekend at this house and would be delighted to return some day. With only one person per bed, though, the max...
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    1 / 25
    Tracys Landing, MD
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Hot Tub
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    • Sauna
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    • Pet-friendly
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    • Smoking allowed
    • 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
    1 / 35
    Cambridge, MD
    7 Bedrooms, 7 Bathrooms, Sleeps 28 | Quick View
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    • Washer
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    • Private Outdoor...
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    • Pet-friendly
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    • ?
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    • x
    About this property
    Captains Quarters on the Bay is a wonderful waterfront home with over 6,000+ Sq. Ft. of Living Space. Designer Appointed with All New Furnishings.7 Bedrooms with 6 Full Bathrooms, some with Jacuzzi/Whirlpool Baths. Gourmet Kitchen with Six Burner Stovetop and Triple Ovens. Large Game Room with... View all property information
    Location Information
    Cambridge, Maryland 21613
    1 / 30
    5 of 5 bubbles (10) Excellent
    Bozman, MD
    8 Bedrooms, 6 Bathrooms, Sleeps 27 | Quick View
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    • Satellite TV
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    • Pet-friendly
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    • ?
    • ?
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    About this property
    Main House: Beautiful NEW kitchen... Featuring two interior eating/serving areas, custom french windows that open to a sitting area on the porch, 4 bedrooms & Enclosed Sleeping Porch 2 ½ baths, fireplace, 3 TV’s, DVD, cable, wireless internet, large living room, dinning room, screened porch,... View all property information
    Location Information
    Bozman, Talbot County 21612
    4 of 5 bubbles Reviewed November 14, 2016
    We thoroughly enjoyed our stay in one of the little cottages on the property. We arrived late Friday night and the property sign was not lit up, so it took a while to find it...
    5 of 5 bubbles Reviewed June 9, 2015
    Perfectly situated on the water. The views are amazing, as is the pool. There is a huge lawn which is perfect for children of all ages. A short drive to St. Michael's, which is a...
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    1 / 18
    4 of 5 bubbles (12) Very good
    Cambridge, MD
    6 Bedrooms, 3 Bathrooms, Sleeps 18 | Quick View
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    • Air Conditioning
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    • Pet-friendly
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    • ?
    • Smoking allowed
    • ?
    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 bubbles Reviewed July 27, 2016
    We got married at Swan's Nest, and had our extended family stay at the house for about a week after the wedding including grandma and small children. Everyone loved it, and the...
    5 of 5 bubbles Reviewed June 13, 2016
    Swan's nest was everything and more for our wedding on June 4th. We rented the property Thursday-Monday and had family, friends and the entire wedding party stay the entire...
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    1 / 9
    North Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • x
    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
    1 / 16
    Cambridge, MD
    6 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • Pet-friendly
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    • x
    • x
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    • x
    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
    1 / 17
    Woolford, MD
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Private Yard
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    • Pet-friendly
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    • x
    • x
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    • x
    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 / 21
    Cambridge, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Washer
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This charming waterfront cottage on 6.5 private acres sits among swans and eagles on Marylands beautiful Eastern Shore. This professionally deorated cottage is packed with modern ammenities and charm. Saltwater Pool, Dock with seating, boat slip, water and electric; canoes and kayaks, woodburning... View all property information
    Location Information
    Cambridge, Maryland 21613
    1 / 28
    Cambridge, MD
    5 Bedrooms, 4 Bathrooms, Sleeps 18 | Quick View
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    • Pet-friendly
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    • ?
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    • x
    About this property
    This beautifully designer furnished waterfront home is located in a very private setting overlooking the Chesapeake Bay and Little Choptank River. The property features magnificent water views, a private dock, fire pit, a large fenced swimming pool, large deck (partially covered), playground and... View all property information
    Location Information
    Cambridge, Maryland 21613
    1 / 22
    Cambridge, MD
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Central Heating
    • Patio
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    • DVD Player
    • Terrace
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    • Pet-friendly
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    • x
    About this property
    From the hosts that have maintained a five star ratings on our cottage vacation rental, we would like to invite you to enjoy a special vacation in our four bedroom 3 full bath luxury estate home in the heart of the Chesapeake Bay. The house has just undergone a complete remodeling and... View all property information
    Location Information
    Cambridge, Maryland 21613
    1 / 31
    Cambridge, MD
    8 Bedrooms, 6 Bathrooms, Sleeps 22 | Quick View
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Experience the best of beautiful Cambridge when you book this magnificent 8-bedroom, 6-bathroom vacation rental house that comfortably sleeps 22. Featuring a splendid waterfront location on a private lane, along with a private outdoor pool, this home promises a memorable retreat! The moment you... View all property information
    Location Information
    Cambridge, Maryland 21613
    1 / 11
    North Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • Private Yard
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    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... View all property information
    Location Information
    North Beach, Calvert County 20714
    1 / 8
    Cambridge, MD
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Amenities & Details
    • Wi-Fi
    • Balcony
    • Parking
    • Satellite TV
    • Terrace
    • Washer
    • Private Yard
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Modern home that has accommodations for more than 10+, with 2 full living room areas, 3 and half baths, Xfinity cable, with flat screen TVs in each of 5 bedrooms. Master with 50", mini fridge, sofa,loveseat, and ensuite master bath. Home is minutes away from some of the finest Eastern Shore Seafood... View all property information
    Location Information
    Cambridge, Maryland 21613
    1 / 30
    Piney Point, MD
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    Suitability
    • Pet-friendly
    • Child-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... View all property information
    Location Information
    Piney Point, Maryland 19975
    1 / 36
    Piney Point, MD
    5 Bedrooms, 4 Bathrooms, Sleeps 15 | Quick View
    Show Prices
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    VACATION AT ANCHORS AWEIGH THIS SUMMER & GET YOUR 4TH NIGHT FREE ON A FUTURE STAY!* / 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... View all property information
    Location Information
    Piney Point, Maryland 19975
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