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Holiday Rentals in Ocean Pines

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    ₹ 16,649 Average
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    Travellers to Ocean Pines are booking January dates now. Secure your holiday home today, and have the perfect trip.
    All 18 Rentals in Ocean Pines
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    Waterfront Home in Ocean Pines with Pier and View!1 / 34
    (5)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    14 Hickory Way1 / 14
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Your Ocean Pines retreat 5 miles from the beach1 / 20
    (17)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Washer
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owners will meet you at the door and set you up for a successful getaway. Plenty of open spaces for a family to enjoy in a simple rancher that is near the beach and bay. Two sunrooms, bbq grill, picnic table, outdoor seating and quiet backyard away from street. Parking for 4 cars off the road....
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    Ocean Pines, Maryland 21811
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Parking
    • Washer
    • Patio
    • Air Conditioning
    • Internet Access
    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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    Ocean Pines, Maryland 21811
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Grill
    • Central Heating
    Suitability
    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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    Ocean Pines, Maryland 21811
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Balcony
    • Terrace
    • DVD Player
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy this quiet, family-friendly home near the water complete with a full kitchen, furnished balcony, backyard, and outdoor fire pit, all just a short walk from a community pool, public parks, and a golf course. On warm days, head to the sandy beaches of Ocean City, just a little over eight miles...
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    Ocean Pines, Maryland 21811
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    • Patio
    • Cable/satellite TV
    • Washer
    • Parking
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come to the enchanting Maryland coast and be charmed by this fully renovated, contemporary townhome with sweeping views of St. Martin's River. With its open and airy layout, this home is ideal for entertaining family and friends. Offering plenty of cozy seating and inviting fireplace, the living...
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    Ocean Pines, Maryland 21811
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • 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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    Ocean Pines, Maryland 21811
    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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    • 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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    Ocean Pines, Maryland 21811
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    Ocean Pines, Maryland 21811
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Deluxe 3 Bedroom Townhouses1 / 18
    (1)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 October 2018
    We enjoyed a week near the Ocean City beach and Assateague island. The condo was comfortable and situated on a channel with boats and a grassy area. Our dog loved being walked...
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    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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    Ocean Pines, Maryland 21811
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Parking
    • Grill
    • Air Conditioning
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>This beautiful home is just a short distance to the North Gate of Ocean Pines, and minutes from Ocean City. This 4 bedroom 3 1/2 bath home features full kitchen, washer, dryer, dishwasher, Microwave, 5 TVs, ping pong table, and a screened in porch. The home is large enough to...
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    Ocean Pines, Maryland 21811
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Waterfront
    • Grill
    • DVD Player
    • Patio
    • Washer
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spend your vacation in sunshine and comfort at this canalfront home in Ocean Pines, where you'll have 60 feet of waterfront and a private dock that can accommodate a 30-foot boat! Enjoy a pair of bikes to take around the neighborhood, as well as a private deck with a gas grill, a ground-floor patio...
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    Ocean Pines, Maryland 21811
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
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    • DVD Player
    • Grill
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    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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    Ocean Pines, Maryland 21842
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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    Studio, 3 Bathrooms, Sleeps 16 Quick View
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    • Parking
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>This newly decorated, 4 bedroom 2 ½ bath home is nestled in the woods in North Ocean Pines. This beautiful home is just a short distance to the North Gate of Ocean Pines, and minutes from Ocean City. This 4 bedroom 2 1/2 bath home features full kitchen, washer, dryer,...
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    Ocean Pines, Maryland 21811
    Holiday Rental House - 3 Bathrooms, Sleeps 16
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Washer
    • Waterfront
    • DVD Player
    • Parking
    • Balcony
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Soak in gorgeous views of the Ocean Pines Yacht Club and Marina from the outdoor deck and three-season sunroom of this spacious bayfront townhome! You'll enjoy an open and inviting living space with a cozy gas fireplace, colorful beachy decor that will set the mood for fun days in the sun, and...
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    Ocean Pines, Maryland 21811
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • DVD Player
    • Parking
    • Grill
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You’ll fall in love with this tranquil wooded retreat overlooking a canal with a private dock for a small boat or to launch your kayaks. You can relax on the deck with a picnic table, a gas and charcoal grill to enjoy dining outdoors, and a porch swing on the lower patio perfect for summer...
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    Ocean Pines, Maryland 21811
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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