Ocean Pines holiday rentals

We found 7,356 holiday rentals — enter your dates for availability
Discover a selection of 118 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:6 Nov - 13 Nov

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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 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 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

What is the most popular type of holiday home accommodation in Ocean Pines?
Based on our research, houses are the most desirable type of holiday home in Ocean Pines. But of course, everyone's idea of the perfect stay differs. Stayz has holiday homes of all sizes and shapes, and we'll help you to find the perfect match.
How much does it cost to rent a holiday home in Ocean Pines?
Property type, length of stay and season are some of the conditions that can influence the price of a holiday home. Simply click on your travel dates to find your perfect fit. From comfy cottages to expansive luxury villas, all Stayz holiday homes provide unbeatable value.
How much does it cost to rent a beach house in Ocean Pines?
Prices for beach houses in Ocean Pines vary depending on the style and size of the property and time of year you're travelling. Simply enter your dates of travel into Stayz and the number of guests to view holiday home options and prices. From there you can use our filters to refine your search results by nearby activities, ratings, amenities and more.
Are there pet-friendly holiday homes in Ocean Pines?
Pack up a suitcase for the pooch in your life because Ocean Pines has 173 stays that welcome pets with open arms. Let your four-legged pal join in on the family trip at one of our pet-friendly holiday homes on Stayz. Simply enter your travel dates then check the "Pets allowed" filter box.
Can I rent a house with a pool in Ocean Pines?
Grab your swimsuit and pool noodle, because there are 128 houses with a private pool in Ocean Pines. Stay at one of these superb holiday homes and you'll enjoy pool days every day. Simply enter your dates into Stayz, then check the "pool" filter to find a place to make a splash!
What are popular home amenities in Ocean Pines?
A nearby waterfront, a lake view and a swimming pool are the most popular home amenities in Ocean Pines. Whether you're taking a trip by yourself, with your other half or a bunch of friends, Stayz can help you find a holiday home that suits your style with all the features you'll enjoy.
Are there large group holiday homes in Ocean Pines?
You can choose from 44 holiday homes in Ocean Pines that can host a group of 10 or more people. Whether you're organising a holiday with extended family or a celebration like an anniversary, there's ample space to get your favourite people together under the same roof.
Are there holiday homes in Ocean Pines that welcome kids?
With 173 family-friendly holiday homes to choose from in Ocean Pines, now is the perfect time to introduce your little ones to the pleasures of travel. Simply click on our "Properties good for families" filter to look for stays that feature conveniences perfect for families on the move, such as multiple bedrooms, pools, hot tubs and bunk beds.
What are the top attractions for families in Ocean Pines?
Keeping the kids entertained during your stay in Ocean Pines is simple with these top family-friendly attractions:

  • Frontier Town Water Park and Golf
  • GlenRiddle Golf Club
  • River Run Golf Club

Are there one-bedroom holiday homes in Ocean Pines?
Yes, there are two one-bedroom properties in Ocean Pines to pick from. A one-bedroom holiday home is a great option if it's only two of you or if you're holidaying alone. Add in more convenience, space and privacy compared to a hotel, and you've got the makings of an unforgettable trip.
Can I find two-bedroom holiday homes in Ocean Pines?
Choose from 14 two-bedroom homes in Ocean Pines. Settle the kids into the second room or fill it with a couple of your nearest and dearest friends. There's a spot for whoever's lucky enough to be joining your journey.
Are there holiday homes with WiFi in Ocean Pines?
Whether you want to keep up with the headlines, make a video call or update your social media accounts, there are 41 holiday homes with WiFi in Ocean Pines. Check the "WiFi" box when searching on Stayz and stay connected on your getaway.
How can I find holiday homes with air conditioning in Ocean Pines?
Ocean Pines has 166 holiday homes where you'll be able to spend your days in air-conditioned comfort. To find a stay on Stayz that features this amenity, enter your desired travel dates and use the convenient filters to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Ocean Pines?
The minimum age requirements can differ across properties on Stayz, so be sure to check the rules of the holiday home in Ocean Pines you want to book. But typically, it's 16, 18 or 21.
How long can I rent a holiday home in Ocean Pines for?
The amount of time you can rent an Ocean Pines holiday home for is down to each property. Just put in your dates of travel to see available options offering longer term stays. They come with all the things you need to make your extended break more enjoyable and convenient, such as kitchens and air conditioning. Some holiday homes may also offer weekly or monthly discounts, so you can stick around for longer for less.