Ocean Pines holiday rentals

We found 7,144 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

Kitchen table
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 AU$2,279
for 7 nights, 1 apartment
AU$326 per night
includes taxes & fees
FAIRWAY TO HEAVEN: GOLF course views and BEACH parking pass

Find spaces that suit your style

Find properties near top attractions in Ocean Pines

Find the best place to stay - Ocean Pines

Image of Patio, Pool Access! Coastal Ocean Pines Cottage

Patio, Pool Access! Coastal Ocean Pines Cottage

Sleeps 3 · 3 bedrooms · 1 bathroom
10 out of 10
exceptional
(3 reviews)
More information about Patio, Pool Access! Coastal Ocean Pines Cottage, opens in a new tab

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Find out more about Ocean Pines

Why visit Ocean Pines

  • Scenic coastal paths: Enjoy leisurely walks along the charming beach esplanade with magnificent ocean views.
  • Family-friendly attractions: Experience fun-filled days with nearby amusement park activities suitable for all ages.
  • Romantic retreats: Relish peaceful moments and intimate strolls along the serene shoreline perfect for couples.
  • Local cultural charm: Explore the relaxed, historical ambience that infuses the neighbourhood with character.
  • Outdoor adventures: Engage in a blend of natural beauty and outdoor activities for a memorable holiday escape.

Popular types of accommodation around Ocean Pines

Welcome to Ocean Pines, Berlin, Maryland, where a blend of coastal charm and relaxed living awaits. Enjoy magnificent ocean views from private holiday homes, cosy apartments, and modern condos. Discover local attractions and scenic experiences, making your stay a memorable retreat. Experience the best in holiday rentals, from ocean pines rentals to peaceful house rentals, ensuring a rejuvenating getaway.

  • Private Holiday Homes: The top choice for visitors, offering spacious and private living environments ideal for families or groups.
  • Condos: A popular option, these self-contained units often come with shared amenities, perfect for a convenient getaway.
  • Apartments: These versatile spaces provide a home-away-from-home experience, suitable for solo travellers and couples.
  • Cottages: Charming and quaint, cottages provide a cosy retreat amidst nature, perfect for a tranquil escape.
  • Villas: Elegant and luxurious, villas offer a premium holiday experience with ample space and upscale features.**

Top attractions near Ocean Pines

Ocean Pines, Berlin, Maryland, offers a delightful escape for those seeking outdoor adventures and romantic beach holidays. Visitors can enjoy the scenic beach and esplanade, perfect for leisurely strolls and relaxation. Families will appreciate the nearby amusement park, while culture enthusiasts can explore the charming local experiences. With its blend of natural beauty and engaging activities, Ocean Pines is an ideal destination for a memorable getaway.

  • Ocean City Boardwalk: A delightful esplanade offering outdoor family and romantic experiences, its ambience enhanced by scenic views, located 10km from Ocean Pines.
  • Ocean City Beach: A charming beach destination with quintessential seaside vibes, positioned 10km from Ocean Pines.
  • Jolly Roger Amusement Park: An exhilarating amusement park providing outdoor and adventurous family fun, situated 8km from Ocean Pines.

Things to do recommended for couples

For a romantic getaway in Ocean Pines, enjoy a sunset stroll along the picturesque beaches of Assateague Island, just a short drive away. Indulge in a candlelit dinner at a charming local restaurant, and take a leisurely bike ride through the scenic trails, soaking in the natural beauty together.

Things to do recommended for families

Families visiting Ocean Pines can enjoy a day at the local family park and explore interactive exhibits at nearby museums, providing a delightful mix of outdoor adventures and educational experiences.

Things to do recommended for groups

Groups visiting Ocean Pines, Berlin, Maryland can enjoy local experiences such as exploring nearby nature trails, engaging in community events and local culinary tours, while appreciating the unique charm of the region.

*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

Whether you are journeying with a group, as a family, with your pets, or seeking extended stays, ensure you apply the appropriate filters. Here are some Stayz booking pointers for you.

  • Traveling to Ocean Pines with a group: Consider the amount of bedrooms required, as well as facilities like a fully equipped kitchen or an outdoor area for group get-togethers. Fortunately, you can apply filters for all these options, and more, on Stayz.
  • Traveling to Ocean Pines with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, alongside ensuring access to suitable amenities, like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can greatly enhance your experience.
  • Taking your pets with you to Ocean Pines: For many, a family holiday isn’t complete without their furry companion. If that resonates with you, then explore Stayz properties that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds to ensure everyone feels right at home.
  • Planning for a long term stay visiting Ocean Pines: If you're seeking holiday lets that offer special rates for month-long stays or more, you've come to the right place. With the appropriate filter, you can effortlessly locate and save on monthly rentals. You might also consider including features such as parking, a well-equipped kitchen, or a private pool in your search.

Where to stay near Ocean Pines

Ocean Pines, Maryland offers a delightful blend of serene beach holidays and family-friendly attractions. Enjoy the scenic, outdoor ambience while exploring charming coastal paths and relaxing near the ocean. The local area exudes a relaxed, historical atmosphere with inviting spaces perfect for romantic getaways and family adventures alike.

  • Ocean City: Located a mere 10km from Ocean Pines, Ocean City is a vibrant coastal city renowned for its outdoor activities and family-friendly atmosphere. The famous boardwalk stretches along the beach, offering an array of shops, restaurants, and amusement rides. Visitors can enjoy a day at the beach, explore the local water park, or indulge in delicious seafood at one of the many dining establishments. The stunning esplanade is perfect for leisurely strolls, while the family beach area ensures fun for all ages, making it an ideal destination for a romantic getaway or a family holiday.
  • Isle of Wight: Just 5km away from Ocean Pines, Isle of Wight is a charming island that offers a delightful mix of outdoor adventures and family-friendly experiences. The boardwalk is perfect for leisurely walks, while the local theatre often showcases engaging performances. Golf enthusiasts will appreciate the scenic courses available on the island. Visitors can take in the beautiful views of the bay and marina, creating a picturesque setting for relaxation or exploration, making it a great spot for both romantic escapes and family outings.
  • Glen Riddle: Situated 5km from Ocean Pines, Glen Riddle is a serene neighbourhood that beckons outdoor enthusiasts and families alike. With access to a picturesque boardwalk and well-maintained golf courses, it offers ample opportunities for recreation. The local beach and esplanade are perfect for unwinding or enjoying family activities. The inviting atmosphere of Glen Riddle makes it a lovely choice for a romantic stroll or a fun-filled day with loved ones, ensuring a memorable stay.

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 MonthTemperaturePrecipitationCloudinessOccupancyPricing
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 Stayz is a breeze

Are you seeking to make your next journey more cost-effective? Being flexible with your travel dates can lead to substantial savings, as prices often fluctuate. Additionally, opting for a longer stay can also yield noteworthy discounts. To discover a Stayz property that aligns with your budget, utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Planning as easy as it gets

Stayz's cutting-edge Trip Board offers you a dedicated space to plan new adventures, pick up from where you last left off, or manage your existing itineraries. You can easily access properties that you've saved or booked, now organised under Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

Frequently Asked Questions

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.

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.

Are all fees included in the Ocean Pines holiday homes prices shown on Stayz?

Stayz 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.

Are there any Ocean Pines holiday homes with parking?

Stayz offers a wide selection of holiday homes 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 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.

Are there any discounts for Ocean Pines holiday homes?

You can find great discounts on holiday homes in Ocean Pines on Stayz, 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.

Can I change or cancel my Ocean Pines holiday home booking on Stayz?

To find Ocean Pines holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.

Can I find long-stay holiday homes in Ocean Pines?

A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

Can I plan a group trip on Stayz?

Stayz'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 favourites, and build the perfect itinerary together.

How early should I book a Ocean Pines holiday home?

Book your Ocean Pines holiday home 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 Stayz booking and occupancy data for 2024 stays.

How much does it cost to rent a holiday home in Ocean Pines?

Prices for holiday homes 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. Stayz offers something for every taste and budget, from affordable homes in Ocean Pines to more spacious homes.

What can I expect from Stayz customer service and StayzCare™ support?

Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.

What is StayzCare™ and how does it work?

Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.

Why should I join Stayz as a host?

Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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