Ocean Pines vacation rentals

We found 7,243 vacation rentals — enter your dates for availability

Select from 198 homes, 23 cottages, and other vacation rentals in Ocean Pines to find one that's perfect for your trip. Whether you’re staying in a vacation home with family or friends, you'll have the amenities you expect and more, which might include parking and a pool. Whatever you're looking for, you're sure to find a rental for everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Ocean Pines

Showing deals for:Feb 13 - Feb 20

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Awesome!
9.6 out of 10, Exceptional, (48 reviews)
Exceptional
(48 reviews)

An escape for all seasons

Berlin, MD

5% off
Price is CA $491
CA $4,714 total
includes taxes & fees
An escape for all seasons

Find spaces that suit your style

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Ocean Pines

Why visit Ocean Pines

  • Scenic Outdoor Activities: Ocean Pines offers stunning ocean views and sandy beaches, perfect for outdoor enthusiasts.
  • Charming Local Atmosphere: Explore nearby towns filled with friendly locals and historical sites that enrich your visit.
  • Golfing Delight: Enjoy a round at the Ocean Pines Golf Club, a highlight for golf lovers.
  • Family-Friendly Fun: Visit nearby amusement parks for exciting activities suitable for all ages.
  • Diverse Accommodation Options: Choose from a range of vacation rentals, including cozy homes and condos.

Popular types of accommodation around Ocean Pines

At Ocean Pines, we offer a diverse selection of vacation rentals that cater to your needs, including houses, condos, and apartments. Whether you're looking for a cozy house in Ocean Pines or a comfortable stay in nearby Ocean City, our platform provides transparent information to help you make the best choice. Enjoy savings and peace of mind as you embark on your Canadian getaway.

  • Houses: A favourite among visitors, these homes offer spacious accommodations ideal for families or groups seeking a home-like atmosphere during their stay in Ocean Pines.
  • Condos: These modern dwellings provide convenient amenities and are perfect for those looking for a blend of comfort and style.
  • Apartments: A practical option for solo travellers or couples, offering all the essentials for a comfortable getaway.
  • Cottages: These quaint retreats offer a charming and intimate atmosphere, perfect for a relaxing escape.
  • Villas: Luxurious and spacious, villas provide an upscale experience for those seeking a bit more indulgence during their stay.**

Top attractions near Ocean Pines

Ocean Pines, Maryland, is a perfect destination for outdoor enthusiasts and couples seeking a beach getaway. With attractions like the Ocean Pines Golf Club and nearby Ocean City Beach, visitors can enjoy a mix of recreation and relaxation. The area offers a variety of experiences, including scenic esplanades and family-friendly amusement parks, making it an ideal spot for cultural adventures and memorable vacations.

  • Ocean City Boardwalk: A vibrant esplanade featuring charming shops, tasty eateries, and fun-filled activities, perfect for couples and families alike. Enjoy romantic strolls or lively outdoor events while soaking in the stunning ocean views.
  • Ocean City Beach: A picturesque sandy beach offering a relaxing atmosphere. Enjoy sunbathing, swimming, or beach sports while listening to the soothing sound of the waves.
  • Jolly Roger Amusement Park: An exciting amusement park filled with thrilling rides and attractions for the whole family. Experience adventure in a fun, outdoor setting that guarantees a memorable day.

Things to do recommended for couples

For a romantic getaway in Ocean Pines, enjoy a round of mini-golf at Maui Golf or Embers Island, both offering fun vibes just 8.0km away. For a unique shopping experience, visit Seacrets, where you can soak up the local atmosphere and explore together.

Things to do recommended for families

Your family will love Northside Park for wellness and relaxation, just 9.7km from Ocean Pines. For adventure, visit Grand Prix Amusements, 6.4km away, or enjoy some fun at the Carousel Ice Skating Rink, also 9.7km from your location. It's a perfect blend of activities.

Things to do recommended for groups

Groups visiting Ocean Pines can enjoy a round of golf at the Bayside Resort Golf Club, indulge in shopping at the Tanger Outlet Center, and explore the Ocean Plaza Mall Shopping Center for a mix of family-friendly and entertaining experiences within a short drive.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Ocean Pines

When planning your trip, whether you're traveling with friends, family, pets, or seeking extended stays, be sure to apply the appropriate filters based on your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Ocean Pines with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Ocean Pines with young kids: Traveling with young children can present its challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Ocean Pines: For many, a family vacation wouldn’t feel complete without their furry companion. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties offer feeding bowls and cozy beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Ocean Pines: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don’t forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Ocean Pines

Ocean Pines, Maryland, offers a delightful blend of outdoor adventures and romantic beach getaways. With its stunning ocean views and sandy beaches, this family-friendly community is perfect for relaxation and recreation. Explore the charming nearby towns and immerse yourself in the local atmosphere, where friendly people and historical sites await. Whether you're seeking a vacation rental or a peaceful retreat, Ocean Pines has something for everyone looking to enjoy the beauty of the Eastern Shore.

  • Ocean City: Located a mere 9.7km from Ocean Pines, Ocean City is a bustling seaside resort renowned for its vibrant boardwalk and family-friendly attractions. This lively city offers a delightful mix of outdoor activities, romantic spots, and family adventures. Stroll along the boardwalk lined with shops and eateries, or spend a day at the water park for some thrilling fun. With beautiful beaches and the scenic esplanade nearby, Ocean City is perfect for those looking to soak up the sun and enjoy a lively atmosphere.
  • Isle of Wight: Situated 4.8km from Ocean Pines, Isle of Wight is an idyllic island offering stunning natural beauty and outdoor adventures. This charming area is ideal for those seeking scenic views and a touch of adventure. Golf enthusiasts can enjoy a round at the local golf course, while nature lovers can explore the serene nature reserve. With family-friendly beaches and picturesque landscapes, Isle of Wight is a fantastic spot for relaxation and outdoor exploration, making it a must-visit destination during your stay.
  • Glen Riddle: Just 4.8km from Ocean Pines, Glen Riddle is a quaint neighborhood that combines outdoor recreation with a romantic atmosphere. This charming area offers access to golf courses and beautiful beaches, perfect for families and couples alike. Visitors can enjoy a leisurely day at the beach or explore the nearby esplanade. Glen Riddle's inviting environment and array of activities, including its proximity to the boardwalk, make it a delightful place for those looking to unwind and connect with nature.

Best time to go to Ocean Pines

If you're planning a trip to Ocean Pines, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January38.1°F (3.4°C)Light RainMostly SunnyAverageSlightly Low
February40.1°F (4.5°C)Light RainMostly SunnyAverageSlightly Low
March45.3°F (7.4°C)Light RainMostly SunnyAverageSlightly Low
April54.5°F (12.5°C)Light RainMostly SunnyAverageAverage
May63.1°F (17.3°C)Light RainMostly SunnyAverageAverage
June72.0°F (22.2°C)Light RainMostly SunnyHighSlightly High
July77.5°F (25.3°C)Light RainMostly SunnyHighSlightly High
August76.3°F (24.6°C)Light RainMostly SunnyHighSlightly High
September71.2°F (21.8°C)Light RainMostly SunnyAverageAverage
October62.1°F (16.7°C)Light RainMostly SunnyLowAverage
November50.9°F (10.5°C)Light RainMostly SunnyLowAverage
December44.1°F (6.7°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay to enjoy substantial savings. To discover a Vrbo property that aligns with your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a user-friendly platform where you can craft new trips, continue from where you paused, or manage your existing plans. You'll find your saved or booked properties neatly organized under Potential, Upcoming, or Current Trips. To begin utilizing Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Ocean Pines?
In Ocean Pines, vacation houses are the most popular rental option, with around 195 available across the community. These properties typically offer spacious interiors, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many also feature outdoor decks or patios, great for enjoying the pleasant Maryland weather. Cottages are another option, with about 22 available, providing a charming, quaint experience for those seeking a more rustic feel. Additionally, there are several condos, mobile homes, and apartments scattered throughout the area, suiting varying preferences and budgets.
Are there any beach house rentals in Ocean Pines?
In Ocean Pines, Maryland, there are approximately 245 beach house rentals available, making it a popular destination for holidaymakers. These rentals are predominantly located in serene neighbourhoods, providing easy access to the nearby beaches and the scenic views of the surrounding area.
How much does it cost to rent a vacation home in Ocean Pines?
Prices for vacation rentals in Ocean Pines vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Ocean Pines to more spacious homes.
Are there any discounts for Ocean Pines vacation house rentals?
You can find great discounts on house rentals in Ocean Pines on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any Ocean Pines vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Ocean Pines with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay vacation rentals in Ocean Pines?
A long-stay vacation rental in Ocean Pines is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Ocean Pines for a vacation rental?
The best time to visit Ocean Pines for a vacation rental is during the peak summer months of June to August, with July being particularly popular. This vibrant season attracts families and beach lovers eager to soak up the sun on the beautiful shores of the Atlantic Ocean. With temperatures averaging around 29°C, it's an ideal time for outdoor activities such as swimming, kayaking, and enjoying the local festivals that bring the community to life.

The abundance of warm weather and lively events makes this period superb for those who thrive in a bustling atmosphere. Visitors can indulge in fresh seafood, explore nearby Assateague Island, and even catch a glimpse of the wild horses that roam the area. The proximity to the beach means your days can be filled with relaxation and fun, all within a short drive or bike ride from your accommodation.

For those seeking a more budget-friendly option, November offers a quieter alternative to the summer crowds, with milder weather around 13°C. This time of year allows for peaceful strolls along the shoreline and the opportunity to experience the off-season charm of Ocean Pines, including local shops and restaurants without the hustle and bustle of peak travel.
Are there any remote work vacation rentals in Ocean Pines?
In Ocean Pines, Maryland, there are numerous remote work vacation rentals available, with around 210 properties to choose from. This charming community, located near the scenic coastal areas, offers a variety of accommodations suitable for those looking to work remotely while enjoying a tranquil setting.

Many of these rentals come equipped with essential amenities for remote work, including Wi-Fi, dedicated desks, ergonomic chairs, and laptop workspaces, ensuring a comfortable and productive environment. Some properties may also feature additional facilities like safe workspaces and even office setups, suiting the needs of digital nomads or professionals looking to balance work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Ocean Pines vacation rental?
Book your Ocean Pines vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Ocean Pines home rental booking on Vrbo?
To find Ocean Pines vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Ocean Pines vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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