Ocean Pines holiday lettings

We found 7,148 holiday rentals — enter your dates for availability
Discover a selection of 117 homes and other holiday rentals in Ocean Pines that are perfect for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll have the best amenities for spending time at your home away from home, which might include parking and a garden. At the end of the day, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Ocean Pines

Showing deals for:29 Jan - 5 Feb

Image gallery for FAIRWAY TO HEAVEN: GOLF course views and BEACH parking pass

Terrace/patio
9.8 out of 10, Exceptional, (74 reviews)
Exceptional
(74 reviews)

FAIRWAY TO HEAVEN: GOLF course views and BEACH parking pass

Berlin

5% off
Price is £1,203
for 7 nights, 1 apartment
£172 per night
includes taxes & fees
FAIRWAY TO HEAVEN: GOLF course views and BEACH parking pass

Find spaces that suit your style

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  • More quality time

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  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Ocean Pines

  • Scenic Parks: Ocean Pines boasts picturesque parks perfect for leisurely strolls and family outings amidst nature.
  • Tranquil Waterways: Experience the serenity of the area's tranquil waterways, ideal for kayaking and fishing.
  • Outdoor Activities: Engage in various outdoor adventures, from cycling to picnicking in the beautiful surroundings.
  • Family-Friendly Atmosphere: The community offers a warm, inviting environment, making it perfect for family vacations.
  • Comfortable Accommodations: Enjoy a range of lodging options, including condos and private homes, tailored for a relaxing stay.

Popular types of accommodation around Ocean Pines

Welcome to Ocean Pines, a charming neighbourhood in Berlin, Maryland, offering a delightful escape for travellers. With its picturesque landscapes and serene environment, Ocean Pines is perfect for those seeking relaxation. Enjoy various attractions, including scenic parks, tranquil waterways, and recreational activities. The most popular types of accommodation here include condos, houses, and apartments, ensuring a comfortable stay tailored to your needs. Discover the warmth and beauty of Ocean Pines for your next getaway.

  • Condos: These modern, multi-storey rental units provide a comfortable stay with amenities, making them the top choice for visitors to Ocean Pines.
  • Houses: Spacious homes offering privacy and a home-like atmosphere, perfect for families or groups seeking relaxation.
  • Apartments: Conveniently located, these self-contained units offer essential comforts for a short getaway.
  • Cottages: Quaint and charming, these small houses provide a cosy retreat close to nature.
  • Villas: Luxurious properties offering upscale living, ideal for those seeking a lavish holiday experience.**

Top attractions near Ocean Pines

Ocean Pines in Berlin, Maryland, offers a delightful blend of outdoor and romantic experiences perfect for a beach vacation. Visitors can explore beautiful beaches, scenic esplanades, and family-friendly amusement parks. With a focus on outdoor activities and cultural experiences, Ocean Pines caters to those seeking relaxation and adventure alike, making it an ideal destination for families and couples looking to enjoy the picturesque surroundings.

  • Ocean City Boardwalk: A vibrant esplanade bustling with shops, eateries, and entertainment, perfect for a romantic stroll or family outing, set against the backdrop of the stunning Atlantic Ocean.
  • Ocean City Beach: Renowned for its golden sands and inviting waters, it's an ideal spot for sunbathing, swimming, and beach games, embodying the quintessential beach vibe.
  • Jolly Roger Amusement Park: A thrilling amusement park featuring rides and attractions for all ages, ensuring an action-packed day filled with adventure and family fun.

Things to do recommended for couples

Searching for a romantic getaway in Ocean Pines? Enjoy a scenic sunset at the beach, indulge in a couples' spa day, or take a leisurely bike ride through the tranquil nature trails. Don't forget to savour a candlelit dinner at a charming local restaurant.

Things to do recommended for families

Families visiting Ocean Pines can enjoy a delightful day at the nearby Assateague Island National Seashore, where children can marvel at wild ponies and explore beautiful beaches. Additionally, the Ocean Pines Community Centre offers fun activities like swimming and sports for all ages, ensuring a memorable family holiday.

Things to do recommended for groups

Groups visiting Ocean Pines can enjoy a delightful day at Assateague Island, where they can see wild ponies and relax on pristine beaches. Additionally, a visit to the charming town of Berlin offers unique shops and local dining experiences, perfect for creating lasting memories together.

*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 travelling with a group, your family, pets, or planning 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'll require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Ocean Pines with young kids: Travelling with young children can present its own set of challenges. It’s essential to prioritise their comfort and safety, alongside ensuring access to suitable amenities, like a private swimming pool. Additionally, it’s wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Ocean Pines: For many, a family holiday isn’t truly fulfilling without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels completely at home.
  • Planning for a long term stay visiting Ocean Pines: If you’re in search of holiday rentals with discounts for stays of a month or more, you’ve come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don’t forget to consider including amenities such as a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Ocean Pines

Ocean Pines, Berlin, Maryland, offers a delightful blend of outdoor adventures and serene relaxation. Nestled near stunning beaches, this charming neighbourhood is perfect for family-friendly outings and romantic getaways. Explore picturesque parks, enjoy leisurely strolls along scenic paths, and indulge in the warm, welcoming atmosphere of the community. With its recreational activities and beautiful landscapes, Ocean Pines promises a memorable escape for all who visit.

  • Ocean City: Located a mere 10km from Ocean Pines, Ocean City is a bustling seaside resort known for its lively atmosphere and stunning beachfront. This vibrant city offers a plethora of outdoor activities, making it perfect for families and couples alike. Stroll along the famous boardwalk, indulge in shopping, or enjoy a day at the water park. Key attractions include the picturesque esplanade and family-friendly beaches, ensuring a fun-filled experience for all visitors.
  • Isle of Wight: Just 5km away from Ocean Pines, Isle of Wight is a charming island that captivates visitors with its natural beauty and outdoor pursuits. Ideal for families and romantic getaways, this location boasts a delightful boardwalk, an engaging theatre, and excellent golf facilities. With scenic views of the bay and a welcoming marina, the Isle of Wight offers a tranquil escape while still being close to popular attractions, such as the esplanade.
  • Glen Riddle: Situated 5km from Ocean Pines, Glen Riddle is a picturesque neighbourhood that offers a perfect blend of outdoor activities and family-friendly experiences. Visitors can enjoy leisurely walks along the boardwalk or hit the golf course for a round or two. With easy access to beautiful beaches and the esplanade, Glen Riddle serves as a serene retreat while providing ample opportunities for fun and relaxation for all ages.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 simple

Looking to cut costs on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Furthermore, opting for a longer stay can often result in significant savings. To discover the ideal Vrbo property that suits your budget, utilise our filters to refine your search by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides you with a dedicated space to plan new adventures, manage your ongoing travel arrangements, or review and organise your bookings. Your saved or booked properties are conveniently categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

How much does it cost to rent a holiday home in Ocean Pines?
Prices for holiday 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 traveling 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. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Ocean Pines holiday 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 holiday rentals with parking?
Vrbo offers a wide selection of holiday 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 holiday rentals in Ocean Pines?
A long-stay holiday 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 holiday rental?
July is the most popular time to visit Ocean Pines, as the summer peak season runs from June to August. During these months, the area buzzes with activity, attracting families and beachgoers eager to soak up the sun along the beautiful Maryland coastline. The warm temperatures, typically ranging from 20 to 30 degrees Celsius, create the ideal setting for outdoor adventures, whether it's enjoying water sports, golfing, or leisurely strolls along the beach.

For those who prefer a more tranquil experience, November presents a fantastic opportunity to visit Ocean Pines at a lower cost. This month offers a quieter atmosphere, allowing visitors to appreciate the natural beauty of the area without the crowds. Crisp autumn air makes for pleasant walks, and the stunning fall foliage adds a unique charm to the landscape.

Ultimately, the best time to book a holiday rental in Ocean Pines hinges on your preferences: if you thrive on vibrant summer activities and community events, July is your month. However, if you seek a peaceful retreat with beautiful scenery, consider a visit in November.
How early should I book a Ocean Pines holiday rental?
Book your Ocean Pines holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Ocean Pines, Maryland, United States of America?
In Ocean Pines, visitors can enjoy a variety of attractions and activities that highlight the area's natural beauty and recreational opportunities. The Ocean Pines Golf Club offers a picturesque 18-hole course surrounded by lush landscapes, great for golf enthusiasts. Nearby, the community boasts several parks such as the community centre, which features walking trails, playgrounds, and sports facilities, making it an ideal spot for families.

For those looking to explore the waterfront, the nearby Assawoman Bay provides opportunities for kayaking, paddleboarding, and fishing, allowing for a relaxing day on the water. Additionally, Ocean Pines is just a short drive from the bustling resort town of Ocean City, where visitors can find famous boardwalk attractions, amusement parks, and beautiful beaches.
Can I change or cancel my Ocean Pines home rental booking on Vrbo?
To find Ocean Pines holiday 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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Ocean Pines holiday 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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