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Holiday Homes and Apartments Hollywood, MD and nearby

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    The following rentals are within 40 kilometres of Hollywood, Maryland.

    1 / 20
    4.5 of 5 bubbles (6) Very good
    Montross, VA
    4 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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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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    1 / 13
    4.5 of 5 bubbles (13) Very good
    Montross, VA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 20
    5 of 5 bubbles (4) Excellent
    Fishing Creek
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
    • Air Conditioning
    • Satellite TV
    • Waterfront
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    • Ocean Views
    • Grill
    • Wi-Fi
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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 / 10
    Saint Leonard
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Waterfront
    • Internet Access
    • Parking
    • Outdoor Dining Area
    • Air Conditioning
    • DVD Player
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Looking for a peaceful beach getaway? Located in quiet Long Beach overlooking Flag Harbor Yacht Haven marina, this cottage is a few minutes walk to the sandy beach along cliffs famous for fossils from the Miocene. The shallow water is safe for children to swim, and a favorite for fishermen and... View all property information
    Location Information
    Saint Leonard, Calvert County 20685
    1 / 38
    5 of 5 bubbles (2) Excellent
    Fishing Creek
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Grill
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    • x
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    • 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 13 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 / 26
    Saint Mary's City
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Wi-Fi
    • DVD Player
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    • Satellite TV
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    • Air Conditioning
    • Ocean Views
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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 / 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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    • 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 / 9
    Fishing Creek
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Grill
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    • Air Conditioning
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    • 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 / 29
    Lusby
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Porch
    • Washer
    • Wi-Fi
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    • Grill
    • DVD Player
    • Children's Pool
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    • 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 / 8
    Lusby
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Pet-friendly
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    • ?
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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 / 17
    5 of 5 bubbles (5) Excellent
    Colonial Beach, VA
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Satellite TV
    • Washer
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Grill
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Marina Sunset is situated on the upper level of a bayfront cottage. 'Incredible' best describes the sunset views of Monroe Bay from the front deck of this gorgeous vacation rental on the 'Point.' This beautifully decorated and fully equipped two-bedroom unit sleeps up to 5 and offers everything... View all property information
    Location Information
    Colonial Beach, Virginia 22443
    5 of 5 bubbles Reviewed 22 December 2016
    I can not say enough about the wonderful vacation we had Sept, 2016. We rented a gulf cart and drove all over!! The location was excellent. The view was amazing! My Husband REALLY...
    5 of 5 bubbles Reviewed 6 August 2016
    My wife, teenage son and I had a totally wonderful experience at MARINA SUNSET! The comfy cottage is very well appointed, decorated and thoughtfully equipped. We rented a golf...
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    1 / 15
    3.5 of 5 bubbles (6) Average
    Colonial Beach, VA
    2 Bedrooms, 1 Bathroom, Sleeps 3 | Quick View
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    • DVD Player
    • Washer
    • Grill
    • Air Conditioning
    • Porch
    • Patio
    • Satellite TV
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Super cute, furnished cottage on the point. 2 bedroom, 1 bath, kitchen, sunroom, covered back patio. Renovated bathroom, hardwood floors, fenced yard. Come relax and enjoy a sunset walk around the point. Nestled on a quiet street two blocks from the Potomac River and two blocks from Monroe Bay.... View all property information
    Location Information
    Colonial Beach, Virginia 22443
    5 of 5 bubbles Reviewed 30 August 2016
    Clean and comfortable- close to everything you need. Home is private and quiet but close to the activities
    3 of 5 bubbles Reviewed 16 August 2016
    I rented this unit with my parents. The rental is advertised as a house with air conditioning. Renters should be aware that this house does not have central air. The unit has 1...
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    1 / 32
    5 of 5 bubbles (1) Excellent
    Piney Point
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Internet Access
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    • Pet-friendly
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    • ?
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    • ?
    About this property
    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 / 17
    Kinsale, VA
    4 Bedrooms, 2 Bathrooms, Sleeps 13 | Quick View
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    • Porch
    • Internet Access
    • Waterfront
    • DVD Player
    • Washer
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    • Satellite TV
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Location: Sandy Point, Virginia, USA (2 Hours from Washington D.C., 1.5 Hours from Richmond, Va) Accommodations: House, 4 Bedrooms + Convertible bed(s), 2 Baths (Sleeps 10-12) 2400 Square Feet It was initially built in 1932 as a fishing cottage and was fully renovated in 2008. The Lodge is... View all property information
    Location Information
    Kinsale, Virginia 22488
    1 / 45
    5 of 5 bubbles (1) Excellent
    Piney Point
    5 Bedrooms, 4 Bathrooms, Sleeps 15 | Quick View
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    • Internet Access
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    • Pet-friendly
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    • ?
    About this property
    PET FRIENDLY* / 10% Military Discount** / View: Community / Sleeps: 15 / 5BR, 4BA single family home About this home: This spacious 5-bedroom, 4-bath single family home - approximately 3,800 square feet - is a great place to relax and enjoy your vacation. This lovely home sleeps 15... View all property information
    Location Information
    Piney Point, Maryland 19975
    1 / 13
    Saint Leonard
    1 Bedroom, Sleeps 2 | Quick View
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    • Waterfront
    • Outdoor Dining Area
    • Internet Access
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
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    • x
    About this property
    Come relax at this charming updated one bedroom bungalow. It overlooks the waters of Wells Cove, a tributary to the Patuxent River which is itself, a tributary to the Chesapeake Bay. This cottage is secluded from the main house, surrounded by water and a wild flower meadow. Somewhat secluded from... View all property information
    Location Information
    Saint Leonard, Calvert County 20685
    1 / 32
    Montross, VA
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Grill
    • Patio
    • Washer
    • Central Heating
    • Waterfront
    • DVD Player
    • Terrace
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Sited high on a private Waterfront hillside w/wide views across the Potomac River at its widest point in Virginia wine country sits this Magnificent Italian Villa. Opportunities like this come rarely. All stucco home with marble floors, custom stairs, gourmet Kitchen with stainless appliances.... View all property information
    Location Information
    Montross, Virginia 22520
    1 / 17
    Saint Leonard
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Parking
    • Private Garden
    • Air Conditioning
    • Internet Access
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The "Sweet Spot" on the Bay - this charming 2 BR 1 Bath Cottage with water views is located in a private waterfront community, Long Beach in St. Leonard, MD, just half a block to the beach (which has a nice big shade tree). This cozy little cottage is super comfy and fully furnished with linens... View all property information
    Location Information
    Saint Leonard, Calvert County 20685
    1 / 9
    North Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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
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    1 / 24
    Colonial Beach, VA
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Porch
    • Grill
    • Patio
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Take leisure to the next level on your upcoming coastal retreat by reserving 'The Blue Crab Cottage,' a traditional bungalow-style Colonial Beach vacation rental home. Supremely located just 2 blocks from the glorious beach and only 4 blocks away from downtown amenities such as municipal halls,... View all property information
    Location Information
    Colonial Beach, Virginia 22443
    1 / 14
    Kinsale, VA
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Private Outdoor...
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    • Pet-friendly
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    • x
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    • x
    About this property
    Tween is located at Sandy Point, Virginia on the Northern Neck. The house is on the waterfront of the Potomac River where it is approximately five miles across to the Maryland shores. You look out onto the Chesapeake Bay from the porch. The beach is sand and the water has a gradual depth increase -... View all property information
    Location Information
    Kinsale, Virginia 22488
    1 / 30
    Piney Point
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Pet-friendly
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    • ?
    • ?
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    • ?
    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
    5 Bedrooms, 4 Bathrooms, Sleeps 15 | Quick View
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    • Pet-friendly
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    • ?
    • ?
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    • ?
    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
    1 / 17
    Woolford
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Private Garden
    • Satellite TV
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    • Secure Parking
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    • Shared Outdoor Pool...
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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 / 11
    North Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • Pet-friendly
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    • 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