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Holiday Homes in Ocean Pines

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    Travellers to Ocean Pines are booking August dates now. Secure your holiday rental today, and have the perfect trip.
    All 16 Rentals in Ocean Pines
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    14 Hickory Way1 / 28
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Moonraker is located in the North gate of Ocean Pines * 4 Large Bedrooms 2 Full baths Large living area and huge Screened in Porch * This home has been renovated with new fully equipped kitchen, flooring all new bedding... it's a home you will want to stay and relax in... and will want to come back...
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    21811, Ocean Pines, Maryland
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    • Shared Indoor Pool
    • Grill
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled around Ocean Pines Golf Course and only 15 minutes from a private beach club, Borderlinks offers an array of onsite resort amenities. Enjoy tennis, indoor/outdoor pools, golf, and scenic bicycling. Take in a day of sun and surf at the private Ocean City Beach Club with a fully equipped...
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    21811, Ocean Pines, Maryland
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Internet Access
    • Grill
    • Cable/satellite TV
    • Patio
    • Parking
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bring the whole crew for your next getaway when you plan your vacation to this family-friendly Ocean Pines home. Boasting access to the Ocean Pines Beach Club and a prime location, you'll be able to unwind and explore the area with ease. Nestled in a quiet neighborhood, this home is set nine...
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    21811, Ocean Pines, Maryland
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Waterfront Home in Ocean Pines with Pier and View!1 / 34
    (4)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Porch
    • DVD Player
    • Washer
    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the beach house at 241 Charleston Rd. in beautiful Ocean Pines, Maryland! Situated at the point of a natural peninsula and nestled in marshland, 241 Charleston is in complete seclusion overlooking the spectacular Ocean City skyline. Jet Ski to Seacrets, kayak, crab, fish, or simply...
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    21811, Ocean Pines, Maryland
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Central Heating
    • DVD Player
    • Waterfront
    • Grill
    • Patio
    • Ocean Views
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to 'Dolphin's Chance', our Ocean Pines water front home, overlooking the scenic St Martin's River and close to Ocean City, MD. This charming two-story home is close to the OC boardwalk, bustling west OC, and the quaint town of Berlin, MD. One can also explore Assateague Island, OC...
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    21811, Ocean Pines, Maryland
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Balcony
    • Shared Indoor Pool
    • Air Conditioning
    • Secure Parking
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3-bedroom, 2-bath townhome sleeps 10 guests. Your stay includes a master bedroom with a private balcony, a second bedroom with a full-sized bed, and two twin beds in the third bedroom. The main floor has a fully equipped kitchen and a large dining table. The living room offers a cozy fireplace...
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    21811, Ocean Pines, Maryland
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Grill
    • Washer
    • Parking
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful coastal cottage with spectacular water view, newly remodeled kitchen, solid maple floors, beach décor, 3 bedrooms 2 bath sleeps up to 8. 3 bedroom, 2 Bath with private waterfront views close to the beach. Enjoy your vacation on a quite cul-de-sac in in well maintained neighborhood, bike...
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    Location Information
    21811, Ocean Pines, Maryland
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Your Ocean Pines retreat 5 miles from the beach1 / 20
    (15)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Grill
    • Hot Tub
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 July 2017
    Had a wonderful vacation in Ocean Pines 4th of July week. This house is beautiful with all amenities needed. I would recommend staying here to all. It was a great retreat...
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    About this property
    Come away to your home away from home! Rent this immaculate, charming, and tastefully decorated single family home in Ocean Pines, Maryland--a beach resort just across the bay from Ocean City. Nestled in a tranquil wooded lot, this modern, single-story 1,500 sq ft cathedral ranch has 3 bedrooms, 2...
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    Location Information
    21811, Ocean Pines, Maryland
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Hot Tub
    • Patio
    • Parking
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come relax in this tranquil farmhouse and leave the daily grind behind. Let the days slip away as you explore the local attractions and soak in your private hot tub. Surrounding you with privacy, while putting you only eight miles from the Ocean City shores, you'll have everything you need close...
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    Location Information
    21811, Ocean Pines, Maryland
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    These townhouses are nested around a golf course. The Ocean City beach and the Beach Club are 15 minutes drive. Interiors feature a full kitchen, laundry, living room, dining area, and two full baths. Play a round of golf, surf the waves, go to a well-equipped gym, see wild horses, savor today’s...
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    Location Information
    21811, Ocean Pines, Maryland
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Parking
    • DVD Player
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Comfortable living spaces, a full kitchen, and a screened-in back porch make this two-bedroom getaway the ideal home away from home for your next visit to Ocean Pines. This rental is just steps from the Ocean Pines Community Center for year-round activities, as well as White Horse Park and the...
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    Location Information
    21811, Ocean Pines, Maryland
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Internet Access
    • DVD Player
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a peaceful canalside vacation at this colorful, nautical-themed home, complete with a furnished porch, deck, and dock. This home is also located close to local parks, shops, and restaurants, and lies just minutes from the Atlantic Coast! Just four miles east, experience everything that Ocean...
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    Location Information
    21842, Ocean Pines, Maryland
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    To secure a do-as-you-please getaway in Berlin, Maryland, be sure to book this charming 2-bedroom, 1-bathroom vacation rental house with flexible accommodations for up to 6! Affiliated with Ocean Pines Resort, this home allows access to the on-site golf course, 5 pools, tennis courts, and marina...
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    Location Information
    21811, Ocean Pines, Maryland
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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