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Holiday Homes in Saint Leonard

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    Don't let other travellers get your favourite Saint Leonard area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 17 Rentals in Saint Leonard
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    New! Beachfront 4BR St. Leonard Cottage w/ Deck!1 / 24
    (1)Excellent
    Saint Leonard
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Saint Leonard
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Saint Leonard
    1 Bedroom, Sleeps 2 Quick View
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    The following rentals are within 30 kilometres of Saint Leonard.
    Seahorse Guest Cottage near the Bay, dog friendly1 / 17
    (5)Very good
    North Beach
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Washer
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 November 2014
    Just as described- walk to boardwalk and shops. Owner right next door, he's thought of everything. Lovely getaway destination.
    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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    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...
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    Location Information
    20714, North Beach, Calvert County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Lusby
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Porch
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Grill
    • DVD Player
    • Children's Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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....
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    20657, Lusby, Calvert County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cedar Beach Lodge is a Modern Year-Round1 / 8
    (2)Excellent
    Lusby
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Porch
    • Internet Access
    • Grill
    • Parking
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    We rented this beautiful, well-kept and well-stocked lodge for a week-long family vacation. Deborah was excellent to work with and accommodating. The house offers plenty of...
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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....
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    20657, Lusby, Calvert County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Fishing Creek, MD
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Grill
    • Housekeeping Included
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Patio
    • Waterfront
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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....
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    21634, Fishing Creek, Maryland
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Best kept secret by the bay (Entire House)1 / 20
    (4)Excellent
    Fishing Creek, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • Housekeeping Included
    • Ocean Views
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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...
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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...
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    21634, Fishing Creek, Maryland
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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    Fishing Creek, MD
    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Wi-Fi
    • Parking
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely home offers all the comforts of home, including a covered porch where you can meditate, read, paint, bird watch and get away from it all, as the quiet natural beauty of the area makes it the perfect retreat! The house features spectacular views of the bay and sunsets from the first...
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    Location Information
    21634, Fishing Creek, Maryland
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 11
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    North Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid 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...
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    Location Information
    20714, North Beach, Calvert County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Tilghman Island Cottage for Six - Near Marina and Knapps Narrows Drawbridge1 / 20
    (6)Excellent
    Tilghman, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Waterfront
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 July 2016
    We had an absolutely wonderful time. The cottage was clean and well appointed. We would definitely go back!
    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...
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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...
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    21671, Tilghman, Talbot County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Chesapeake Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Parking
    • Grill
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note that the homeowner lives on site, in a completely separate unit, and may be present during your stay* This ground floor 1-bedroom, 1-bathroom Chesapeake Beach vacation rental apartment is perfect for a couples retreat. The newly renovated property is outfitted with everything you...
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    20732, Chesapeake Beach, Calvert County
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    North Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    20714, North Beach, Calvert County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Hoopers Island Studio, 360 Degrees WATER VIEWS1 / 38
    (3)Excellent
    Fishing Creek, MD
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Grill
    • Patio
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Memories of the peace, beauty and comfort of Fishing Creek, Maryland and of the sparkling, colorful Queen Anne Cottage that is Hoopers Island Haven warm my cold winter days! If...
    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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    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 $25 extra per night Ironman/Eagleman/Event/Holiday $75 extra per stay Discounted weekly rates....
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    Location Information
    21634, Fishing Creek, Maryland
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Chesapeake camping. 40 miles to Wash DC. 1 mile to river. 10 miles to Ches Bay.1 / 21
    (1)Excellent
    Huntingtown
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Secure Parking
    • Wi-Fi
    • Private Garden
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 July 2017
    We can't get enough of this place! Been coming here since 2016 just to get away. Love the changes each season brings! The park and the town center have everything u need. The...
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    About this property
    Chesapeake Camping in Huntingtown, Maryland. 31' Rockwood 8313SS travel trailer in good condition, owners still use for travel. Private gravel site on 26 acre farm with water & electric hookups and dump tank on site. Two separate bedrooms, priv bath with shower/tub combo. Fully equipped kitchen,...
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    Location Information
    20639, Huntingtown, Calvert County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    North Beach
    2 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Terrace
    • Washer
    • DVD Player
    • Central Heating
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 - 8 Outstandingly beautiful, light-filled custom-built home with stunning, views of the wonderful Chesapeake Bay in the picturesque town of North Beach. Steps away from the wonderful boardwalk by the bay. Within a 38-min drive from Washington...
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    Location Information
    20714, North Beach, Calvert County
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 6
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    Woolford, MD
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    • Secure Parking
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    21677, Woolford, Maryland
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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