We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals in Ocean Pines

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    €163 Average
    |||
    |||
    €0€1,000+
    Suitability
    More filters
    Travellers to Ocean Pines are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    All 17 Rentals in Ocean Pines
    Sort by:
    Default
    14 Hickory Way1 / 14
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Studio, 3 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Ocean Pines, Maryland 21811
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Your Ocean Pines retreat 5 miles from the beach1 / 20
    (16)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Grill
    • Hot Tub
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 days ago
    Stayed two week at this beach home! Very comfortable, clean and great location.The home had everything we needed and eating out or carry out was hassle free.We paid the...
    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...
    See all reviews
    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...
    View all property information
    Location Information
    Ocean Pines, Maryland 21811
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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....
    View all property information
    Location Information
    Ocean Pines, Maryland 21811
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    Make Enquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Ocean Pines, Maryland 21811
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Ocean Pines, Maryland 21811
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    Waterfront Home in Ocean Pines with Pier and View!1 / 34
    (4)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Ocean Pines, Maryland 21811
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Ocean Pines, Maryland 21811
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Save time - get the best Ocean Pines rentals sent straight to your email!
    Get the List
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Ocean Pines, Maryland 21811
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Ocean Pines, Maryland 21811
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Ocean Pines, Maryland 21811
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Ocean Pines, Maryland 21811
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 7
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Ocean Pines, Maryland 21811
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Ocean Pines, Maryland 21842
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Ocean Pines, Maryland 21811
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    List your property
    Owner log in