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Holiday Rentals and Homes in Saint Leonard, MD

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    1 / 10
    Saint Leonard
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 17
    Saint Leonard
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 13
    Saint Leonard
    1 Bedroom, Sleeps 2 | Quick View
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    The following rentals are within 40 kilometers of Saint Leonard, Calvert County, Maryland.

    1 / 17
    4.5 of 5 bubbles (5) Very good
    North Beach
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    • DVD Player
    • Waterfront
    • Satellite TV
    • Air Conditioning
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    • Washer
    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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 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 bubbles 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 / 32
    5 of 5 bubbles (1) Excellent
    Coles Point, VA
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Washer
    • Satellite TV
    • DVD Player
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    • Grill
    • Waterfront
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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. 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 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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    1 / 20
    5 of 5 bubbles (4) Excellent
    Fishing Creek, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Washer
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    • Ocean Views
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    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 4 October 2016
    This rental property was amazing. My husband and I stayed for 5 days. We were in town for the Ironman race and wanted to find somewhere a bit away from all the crowds. Hoopers...
    5 of 5 bubbles Reviewed 20 June 2016
    This beautiful home offers everything, and more, one could ask for in a vacation rental. The view of the water is spectacular and we were able to enjoy those views in the comfort...
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    1 / 9
    Fishing Creek, MD
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
    • Wi-Fi
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    • Waterfront
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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 / 26
    Saint Mary's City, MD
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Wi-Fi
    • DVD Player
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    • Air Conditioning
    • Ocean Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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 / 25
    Tracys Landing, MD
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Hot Tub
    • Waterfront
    • Sauna
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • 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 / 29
    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
    • Child-friendly
    • ?
    • 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 / 16
    Cambridge, MD
    6 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • Wi-Fi
    • Balcony
    • Air Conditioning
    • Washer
    • Terrace
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • 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 / 26
    5 of 5 bubbles (1) Excellent
    Cobb Island, MD
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Washer
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    • Internet Access
    • DVD Player
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    • Waterfront
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Cobb Island, Maryland 20625
    1 / 42
    5 of 5 bubbles (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
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    1 / 9
    North Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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 / 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
    • Child-friendly
    • x
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    • 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
    Location Information
    Piney Point, Maryland 19975
    1 / 5
    3 of 5 bubbles (1) Average
    Cambridge, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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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
    1 / 20
    5 of 5 bubbles (6) 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
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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 21 July 2016
    We had an absolutely wonderful time. The cottage was clean and well appointed. We would definitely go back!
    5 of 5 bubbles 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...
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    1 / 29
    5 of 5 bubbles (1) Excellent
    Piney Point, MD
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    PET FRIENDLY* / Sleeps: 10 / View: Community / 3BR, 3BA townhome About this home: This spacious Bayside resort 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 floor... View all property information
    Location Information
    Piney Point, Maryland 19975
    1 / 11
    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
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    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 / 30
    5 of 5 bubbles (10) Excellent
    Bozman, MD
    8 Bedrooms, 6 Bathrooms, Sleeps 27 | Quick View
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    • Satellite TV
    • Patio
    • Internet Access
    • Washer
    • Air Conditioning
    • Grill
    • Private Outdoor...
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    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 2 weeks ago
    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 9 June 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 / 38
    5 of 5 bubbles (2) Excellent
    Fishing Creek, MD
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Grill
    • Patio
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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 12 August 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 / 24
    5 of 5 bubbles (6) Excellent
    Cambridge, MD
    7 Bedrooms, 6 Bathrooms, Sleeps 28 | Quick View
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    • Private Outdoor...
    • Waterfront
    • Hot Tub
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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 bubbles Reviewed 30 April 2016
    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 bubbles 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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    1 / 20
    Deale, MD
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Housekeeping...
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Sauna
    • Washer
    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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 / 30
    4.5 of 5 bubbles (12) Very good
    Cambridge, MD
    6 Bedrooms, 5 Bathrooms, Sleeps 20 | Quick View
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    • Air Conditioning
    • Waterfront
    • Hot Tub
    • Satellite TV
    • Internet Access
    • Sauna
    • Private Outdoor...
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    5 of 5 bubbles Reviewed 12 July 2016
    Our family gathering was everything we hoped because of this vacation home. The house met the needs for the 13 of us, from 4 to 67 years old. We especially loved the different...
    4 of 5 bubbles 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...
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    1 / 20
    Cambridge, MD
    8 Bedrooms, 6 Bathrooms, Sleeps 23 | Quick View
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    • Washer
    • Terrace
    • Waterfront
    • Balcony
    • Grill
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • 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
    1 / 18
    Neavitt, MD
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Patio
    • Balcony
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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 / 18
    4 of 5 bubbles (12) 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
    • Child-friendly
    • ?
    • 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 27 July 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 13 June 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 / 17
    Woolford, MD
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Private Garden
    • Satellite TV
    • Wi-Fi
    • Secure Parking
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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 / 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
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    1 / 39
    Cambridge, MD
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Porch
    • DVD Player
    • Parking
    • Waterfront
    • Grill
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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 / 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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    • Internet Access
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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 14 May 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 / 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
    • Child-friendly
    • ?
    • 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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    Lusby
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Amenities & Details
    • Internet Access
    • Parking
    • Air Conditioning
    • Washer
    • Satellite TV
    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
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    • Smoking allowed
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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