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Holiday Rentals and Homes in Saint Leonard, MD

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

    Clements, MD
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 20
    5 of 5 stars (2) Excellent
    Fishing Creek, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Washer
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    • Ocean Views
    • Grill
    • Wi-Fi
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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
    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 15 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 / 45
    5 of 5 stars (1) Excellent
    Piney Point, MD
    5 Bedrooms, 4 Bathrooms, Sleeps 15 | Quick View
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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
    5 of 5 stars Reviewed 28 June 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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    1 / 34
    Piney Point, MD
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    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 / 7
    5 of 5 stars (9) Excellent
    Bozman, MD
    4 Bedrooms, 2 Bathrooms, Sleeps 13 | Quick View
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    • Satellite TV
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    • Patio
    • Air Conditioning
    • Porch
    • Washer
    • Waterfront
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    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 queens, 1 double, daybed w/trundle, 5 twins) 2 ½ baths, fireplace, 3 TV’s, DVD, cable, wireless internet, large... View all property information
    Location Information
    Bozman, Talbot County 21612
    5 of 5 stars 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...
    5 of 5 stars Reviewed 5 November 2012
    This house was the perfect size for our staff of 8 for our annual staff retreat. The rooms were comfortable. The size of the dining room table was great for our meetings. We...
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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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    • Internet Access
    • Patio
    • Waterfront
    • Grill
    • Porch
    • Outdoor Dining Area
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    The ambience of each cottage is one of relaxed comfort. Fashionable cottage decor is enhanced with coordinating spreads & dust ruffles, moldings, 2” wood blinds, valences, sofas, wing and lounge chairs and collectibles. All the cottages are fully furnished including solaria porch, gas... View all property information
    Location Information
    Bozman, Talbot County 21612
    5 of 5 stars Reviewed 30 September 2013
    Our family has been vacationing at Grandview for over 20 years. I think that says it all. Beautiful location, gorgeous sunsets, peaceful and quite. Serene. Plenty of crabbing...
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    1 / 49
    4 of 5 stars (1) Very good
    Deale, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
    • Satellite TV
    • Wi-Fi
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    • Washer
    • Hot Tub
    • Ocean Views
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    About this property
    This 3 bedroom/2 bath cottage is just the spot for a get-away with other couples or your entire family! Nestled on 2 country-like acres in a surprisingly convenient corner of the Chesapeake Bay, this unique area is just over 20 minutes south of Annapolis and 45 minutes from Wash DC, Alexandria VA,... View all property information
    Location Information
    Deale, Maryland 20733
    4 of 5 stars Reviewed 20 October 2015
    We hosted my husband's 30th birthday party here and it was wonderful! Such a lovely spot on the Chesapeake. Very relaxing. Kids and adults alike had a great time and we would...
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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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    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
    3 of 5 stars Reviewed 26 October 2012
    This is a lovely older house with lots of room for families. We are very grateful that she accepts dogs and even better that the house is so clean you can't tell that dogs have...
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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
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    • DVD Player
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    • Waterfront
    • Satellite TV
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    • Pet-friendly
    • Wheelchair 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
    5 of 5 stars Reviewed 28 December 2011
    I only have great things to say about Ed Mullan's Cobb Island rental. Having stayed there for several weekends, I can attest to the comfortable and well-appointed house, fantastic...
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    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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    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 stars Reviewed 14 July 2015
    This was a perfect setting for our family vacation. Our grandkids ages range from 4-17 and they all enjoyed biking, kayaking, swimming, fishing and playing in the sand. The...
    5 of 5 stars Reviewed 27 June 2015
    Our extended family (22 people - 13A/9K) had a great week at Saddle Beach. The house was beautiful and in very good condition. The option of being in the pool or the river...
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    1 / 38
    5 of 5 stars (2) Excellent
    Fishing Creek, MD
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Grill
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    • Pet-friendly
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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 stars 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...
    5 of 5 stars Reviewed 9 June 2014
    As soon as we stepped out of our car, we felt like we hit the jackpot. The views in front and in back of the house are breathtaking, with water stretching to the...
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    Lusby
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Porch
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    • DVD Player
    • Children's Pool
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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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
    1 / 24
    Churchton, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
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    • Internet Access
    • Hot Tub
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • 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
    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
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    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
    5 of 5 stars Reviewed 2 November 2012
    Our best vacation yet! The owners of this home have truly though of everything. We crabbed and fished right off the dock and caught enough crabs and fish for dinner almost every...
    5 of 5 stars Reviewed 18 October 2012
    We spent a week a Swan cove. the entire Family loved the house. Very spacious, clean and the kids had a blast in the pool. Great setting with the private dock, fire pit...
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    North Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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
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    5 of 5 stars (5) Excellent
    Tilghman, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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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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    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
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    • Wi-Fi
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    • Pet-friendly
    • Wheelchair access
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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 / 24
    Piney Point, MD
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
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    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
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    Saint Mary's City, MD
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Wi-Fi
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    • Air Conditioning
    • Ocean Views
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    Our squeaky clean, fully renovated Cottage with comfortable interior and nice woodland views has cozy CENTRAL HEAT, plus two pretend fireplaces, and a FIREPIT. During the summer re-freshing breezes blow off the Potomac River but central AIR CONDITIONING is there for the muggy days. We are about... View all property information
    Location Information
    Saint Mary's City, Maryland 20690
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    Lusby
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Porch
    • Internet Access
    • Grill
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    • DVD Player
    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • 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
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    5 of 5 stars (5) 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
    • Wheelchair access
    • Child-friendly
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    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
    5 of 5 stars Reviewed 21 May 2014
    I had my wedding at this property. The landlord, Frank, was very polite and easy going. He allowed for our dogs to stay for a low fee and was very good at returning calls. The...
    5 of 5 stars Reviewed 2 November 2012
    Our family cant thank you enough for the memories made at captains quarters this summer. This was the first time getting away with the entire family (kids grandkids, grand...
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    1 / 12
    Deale, MD
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Waterfront
    • DVD Player
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    • Air Conditioning
    • Balcony
    • Porch
    • Satellite TV
    • Parking
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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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
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    Cambridge, MD
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Porch
    • DVD Player
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    • Waterfront
    • Grill
    • Air Conditioning
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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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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    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
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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
    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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    Tilghman, MD
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Get away and stay in our cozy cottage that sits on the Knapp's Narrows in Tilghman, MD. Captain's Watch is a Waterfront Cottage which has a screened porch with beautiful sunrise view of Knapps Narrows. It is nestled in a Working Watermens Village, 12 miles from Historic St. Michaels, Maryland on... View all property information
    Location Information
    Tilghman, Talbot County 21671
    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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    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
    Deale, MD
    2 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • DVD Player
    • Housekeeping...
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Sauna
    • Parking
    • Shared Garden
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • 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
    Neavitt, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Wi-Fi
    • Private Garden
    • Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • 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 / 11
    Lusby
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Parking
    • Air Conditioning
    • Washer
    • Satellite TV
    • Grill
    • DVD Player
    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
    Location Information
    Lusby, Calvert County 20657