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Ocean Pines Vacation Rentals

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    OCEAN CITY - OCEAN PINES - BEACH HOUSE - WALK TO BEACH - FREE BEACH PARKING1 / 11
    (1)Excellent
    Ocean Pines
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Beach Access from This Ocean Pines Beauty!1 / 12
    (2)Very good
    Ocean Pines
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    14 Hickory Way1 / 42
    (2)Excellent
    Ocean Pines
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Ocean Pines
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Grill
    • 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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Ocean Pines
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Internet Access
    • Grill
    • Satellite TV
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    • 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 miles...
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    Ocean Pines, Maryland 21811
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Ocean Pines
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    Pet friendly
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    Ocean Pines, Maryland 21811
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Your Ocean Pines retreat 5 miles from the beach1 / 20
    (15)Excellent
    Ocean Pines
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Grill
    • Hot Tub
    • Satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    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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    Ocean Pines, Maryland 21811
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Modern and Comfortable-Get-a-way to Ocean City minus the crowds1 / 11
    (18)Excellent
    Ocean Pines
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
    • Shared Indoor Pool
    • Internet Access
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
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    Ocean Pines, Maryland 21811
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Waterfront Home in Ocean Pines with Pier and View!1 / 34
    (4)Excellent
    Ocean Pines
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Porch
    • DVD Player
    • Washer
    • Waterfront
    • Air Conditioning
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    • 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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    Ocean Pines, Maryland 21811
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Ocean Pines
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
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    • Housekeeping Included
    • Washer
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    • Satellite TV
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    Ocean Pines, Maryland 21811
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Ocean Pines
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Ocean Pines, Maryland 21811
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ocean Pines
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Balcony
    • Washer
    • Patio
    • Terrace
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    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the Ocean Pines Community 5-10 minute drive outside of Ocean City. Ocean Pines has a private beach club in Ocean City with an outdoor pool and designated parking. Indoor heated pool and outdoor pools available in the Ocean Pines community. Hiking paths, 2 large community ponds stocked...
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    Ocean Pines, Maryland 21811
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    Ocean Pines
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Grill
    • Shared Indoor Pool
    • Satellite TV
    • DVD Player
    • Patio
    • Air Conditioning
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Ocean Pines, Maryland 21811
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Ocean Pines
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
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    • Internet Access
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Ocean Pines, Maryland 21811
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    Ocean Pines
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Grill
    • Internet Access
    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Ocean Pines, Maryland 21811
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Relaxing Family Friendly Beach House in Ocean Pines1 / 15
    (5)Very good
    Ocean Pines
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Satellite TV
    • Washer
    • Internet Access
    • Air Conditioning
    • Shared Indoor Pool
    • Grill
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Ocean Pines, Maryland 21811
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Spacious, well maintained, 3br, 3bath home overlooking Ocean Pines Golf Course1 / 23
    (6)Very good
    Ocean Pines
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Grill
    • DVD Player
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Ocean Pines, Maryland 21811
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    Ocean Pines
    6 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    • Internet Access
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    • Patio
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    Pet friendly
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    Smoking allowed
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    Location Information
    Ocean Pines, Maryland 21811
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 10
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    waterfront beach retreat with boat dock1 / 24
    (9)Very good
    Ocean Pines
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
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    • Patio
    • Washer
    • DVD Player
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Ocean Pines, Maryland 21811
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Ocean Pines
    4 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Patio
    • Grill
    • Air Conditioning
    • Washer
    • DVD Player
    • Internet Access
    • Satellite TV
    • Shared Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Ocean Pines, Maryland 21811
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 14
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    Charming Cottage Near Ocean City/Assateague Island1 / 9
    (19)Excellent
    Ocean Pines
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Satellite TV
    • Washer
    • Air Conditioning
    • Grill
    • Patio
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Ocean Pines, Maryland 21811
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ocean Pines
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Parking
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Satellite TV
    • Washer
    • Grill
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Ocean Pines, Maryland 21811
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Fabulous, Spacious Beautiful home on Quiet Street and close to everything1 / 22
    (4)Very good
    Ocean Pines
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Satellite TV
    • Hot Tub
    • Internet Access
    • Patio
    • Air Conditioning
    • Washer
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Ocean Pines, Maryland 21811
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Spacious Waterfront home with dock, sleeps 14 with pool table1 / 19
    (9)Very good
    Ocean Pines
    8 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    • DVD Player
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Satellite TV
    • Grill
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Ocean Pines, Maryland 21811
    Rental Home - 8 Bedrooms, 3 Bathrooms, Sleeps 16
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    Ocean Pines
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Internet Access
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    Pet friendly
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    Smoking allowed
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    Location Information
    Ocean Pines, Maryland 21811
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Waterfront*Private Hot Tub*WiFi*Bikes*Kayak*Gas Fire Pit*OP beach club parking1 / 23
    (11)Excellent
    Ocean Pines
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Patio
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    • Washer
    • Shared Indoor Pool
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Ocean Pines, Maryland 21811
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    L**K...Gorgeous!!! 2 Master Bedroom Suites!1 / 24
    (5)Excellent
    Ocean Pines
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Shared Indoor Pool
    • Washer
    • Grill
    • Patio
    • Air Conditioning
    • DVD Player
    • Housekeeping Included
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Ocean Pines, Maryland 21811
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    The following rentals are within 5 miles of Ocean Pines.
    Glen Riddle Townhouse 2 miles from Ocean City, MD1 / 9
    (5)Excellent
    Berlin
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Sauna
    • Patio
    • Satellite TV
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    The townhouse location was absolutely fabulous! Location from the beach is unbeatable. You got thw convenience of being close but yet far enough away to not deal with the noise...
    Reviewed July 9, 2017
    This was our first time staying in Glen Riddle. The private gated community settled on two golf courses in nothing short of beautiful!! From our condo it was a short walk to the...
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    About this property
    Glen Riddle Gated Community located on two golf courses 2 miles from Ocean City, MD. Large swimming pool, Clubhouse w/ fitness room, pool table, table tennis, kids play room, 2 tennis courts, and sauna. Marina with boat slip. Great place to ride bikes. Close to Tanger Outlet, Casino,and many...
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    Berlin, Maryland 21811
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    Berlin
    8 Bedrooms, 7 Bathrooms, Sleeps 21 Quick View
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    • Grill
    • Internet Access
    • Patio
    • Washer
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make your next family reunion or group retreat a memorable one at this eight-bedroom West Ocean City property, an expansive estate and adjacent farmhouse with incredible amenities that include a private swimming pool, two hot tubs, a well-stocked game room with a wet bar, and plentiful outdoor...
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    Location Information
    Berlin, Maryland 21811
    Rental Home - 8 Bedrooms, 7 Bathrooms, Sleeps 21
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    Back Bay Bungalows - Unit 11 / 28
    (13)Excellent
    Berlin
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Porch
    • Air Conditioning
    • Satellite TV
    • Waterfront
    • DVD Player
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 21, 2016
    We stayed at Back Bay Bungalows for 3 nights. We wish it had been more. The rooms were very clean and nicely decorated. The views were wonderful. We spent a lot of time just...
    Reviewed September 19, 2015
    It is clear that the owner really cares about the Back Bay Bungalows. The cottages are charming, well equipped, modern, and clean. The grounds and surrounding bay access draw...
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    About this property
    Across the bay from Ocean City, MD., Back Bay Bungalows is a two acre peninsula with great views and deep water access to the bay. This unit has great waterfront views and access. Our property features a boat ramp, two fishing and crabbing piers, kayaks, volleyball/badminton court, hammocks, sandy...
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    Location Information
    Berlin, Maryland 21811
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Ocean Pines Ocean Parkway 1101 / 19
    (1)Excellent
    Berlin
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Balcony
    • Internet Access
    • Terrace
    • Washer
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 7, 2016
    Execllent property! I look forward to staying with them again in the future! The location was just right and it was not too far from the beach
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    About this property
    Ocean Pines - Ocean Parkway 110 Spacious Pet-Friendly Home - Access to Ocean Pines Parking Lot on 49th St. in Ocean City! Ocean Parkway 110 in Ocean Pines is the perfect spot for your family vacation! Spacious, relaxing and comfortable, this lovely 3-BR, 2-BA home features WiFi, a garage, fully...
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    Location Information
    Berlin, Maryland 21811
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Berlin
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Balcony
    • Internet Access
    • Washer
    • Satellite TV
    • Patio
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful manor - styled home in newer luxury resort community with indoor & outdoor pools, fishing lake, tennis courts, crabbing pier, kayak docks, state-of -the-art fitness center, clubhouse, game rooms, playground. Luxury home offers front porch and balcony off bedrooms, recessed lighting,...
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    Location Information
    Berlin, Maryland 21811
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Berlin
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Grill
    • DVD Player
    • Central Heating
    • Washer
    • Patio
    • Waterfront
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One-of-a-Kind Bayfront Estate Vacation at your very own waterfront estate! Assateague Bay Retreat is an exquisite 5,000-SqFt, 4-BR, 4-BA home (plus dens & loft) located in the bayfront golfing community of Rum Pointe. Situated on a 3-acre lot along the Sinepuxent Bay with a shared dock, this...
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    Location Information
    Berlin, Maryland 21811
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    Berlin
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
    • Parking
    • DVD Player
    • Air Conditioning
    • Balcony
    • Terrace
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Suitable for up to eight lucky guests, this luxurious, three-level villa home features multiple living areas, furnished decks, and access to several deluxe, on-site amenities through the Bayside Resort. With the Stephen Decatur Highway to the west and Assateague State Park dominating to the east,...
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    Berlin, Maryland 21811
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Berlin
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    This beautiful 2 bedroom cottage sleep 6 and includes a fully functional kitchen (stove/oven, microwave,coffee maker, refrigerator), cookware and utensils, full bath (shower/tub combo), furnished living room with cable TV, wireless internet, heat & a/c. The cottage does have a porch with a ceiling...
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    Berlin, Maryland 21811
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Berlin
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
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    • Porch
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Deluxe Park Model Cabin sleeps up to 6 people and comes fitted with a screened-in porch, master bedroom with queen-size bed, second bedroom with 1 twin-size bed and 1 full-size bed, full-size sectional sleeper sofa, full-size shower and bathroom. Other features include central AC/heat, color TV...
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    Location Information
    Berlin, Maryland 21811
    Cabin - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Ocean Pines Flight and Weather Info
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