Ocean Pines vacation rentals

We found 7,136 vacation rentals — enter your dates for availability

Select from 113 homes, 18 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:Mar 13 - Mar 20

Image gallery for W. Fenwick Beach Retreat-Saltwater Pool and Canal Front! Minutes to Fenwick & OC

Pool
10 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)

W. Fenwick Beach Retreat-Saltwater Pool and Canal Front! Minutes to Fenwick & OC

Selbyville, DE

12% off
Price is $376
$2,631 for 7 nights
All fees included
W. Fenwick Beach Retreat-Saltwater Pool and Canal Front! Minutes to Fenwick & OC

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Find out more about Ocean Pines

Why visit Ocean Pines

  • Outdoor Activities: Ocean Pines is perfect for outdoor adventures, offering beautiful beaches and scenic esplanades for exploration.
  • Charming Beach Town: Experience the serene atmosphere and stunning views, ideal for family getaways and romantic escapes.
  • Diverse Accommodation: Choose from a variety of rentals, including cozy beach homes, spacious condos, and trendy Airbnbs.
  • Family-Friendly Attractions: Enjoy nearby amusement parks and attractions that cater to families and cultural experiences.
  • Proximity to Ocean City: Explore the vibrant attractions of Ocean City, just a short drive away for more vacation fun.

Popular types of accommodation around Ocean Pines

Planning a getaway to Ocean Pines? You're in for a treat. Explore a variety of popular vacation rentals, including private homes, condos, and apartments. Whether you're seeking cozy beach rentals, spacious house rentals, or trendy Airbnbs, Ocean Pines has something for every traveler. Check out nearby Ocean City, MD, for even more vacation options, and get ready for a memorable escape.

  • Houses: The top choice for visitors in Ocean Pines, offering spacious and comfortable settings perfect for families or groups.
  • Condos: A popular option that provides modern amenities and often stunning views, ideal for couples or small families.
  • Apartments: A convenient choice for travelers looking for a home-like atmosphere with easy access to local attractions.
  • Cottages: Charming and cozy, these rentals are perfect for those seeking a quaint getaway experience.
  • Villas: Luxurious accommodations that offer a blend of comfort and style for an upscale vacation experience.**

Top attractions near Ocean Pines

Ocean Pines, located near Berlin, Maryland, is perfect for outdoor escapades, romantic getaways, and beach vacations. Visitors can explore beautiful beaches, enjoy the scenic esplanade, and have fun at nearby amusement parks. With attractions that cater to families and those seeking cultural experiences, Ocean Pines offers a delightful mix of activities for every traveler. Don't miss out on the charm and adventure this lovely area has to offer.

  • Ocean City Boardwalk: This lively esplanade offers a delightful mix of romance and family-friendly activities, featuring charming shops, delicious eateries, and stunning ocean views, all just 6 miles from Ocean Pines.
  • Ocean City Beach: Experience the quintessential beach vibes at this beautiful sandy stretch, perfect for sunbathing, swimming, and beach games, located 6 miles away from your base in Ocean Pines.
  • Jolly Roger Amusement Park: Just 5 miles from Ocean Pines, this amusement park is a thrilling destination with rides and attractions perfect for families seeking adventure and outdoor fun.

Things to do recommended for couples

Ready for a romantic getaway in Ocean Pines? Start with a fun evening at Seacrets, just 5 miles away, then enjoy a round of mini-golf at Maui Golf. Don't forget to savor the exquisite wines at Costa Ventosa Vineyard and Winery, located 6 miles from your stay.

Things to do recommended for families

Your family will have a blast at Northside Park, just 6 miles away, enjoying the serene atmosphere. For some excitement, head to Grand Prix Amusements, 4 miles away, for thrilling karting fun. Don’t miss the Carousel Ice Skating Rink, also 6 miles away, perfect for some adventurous ice skating.

Things to do recommended for groups

Your group can enjoy a visit to Seacrets Distilling Company for a lively atmosphere, play a round at Bayside Resort Golf Club for some outdoor fun, or shop at Tanger Outlet Center for a variety of entertainment and family-friendly options, all within 5 miles of Ocean Pines.

*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

If you're traveling with a group, with family, bringing your pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Ocean Pines with a group: Think about how many bedrooms you'll require, along with features like a fully-equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Ocean Pines with young kids: Traveling with little ones can be tough. It's important to prioritize their comfort and safety, along with finding age-appropriate amenities like a private pool. Additionally, 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 by their side. If that resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every family member feels at home.
  • Planning for a long term stay visiting Ocean Pines: If you're seeking vacation rentals with special offers 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 rentals. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay near Ocean Pines

Ocean Pines, located near Berlin, Maryland, offers an idyllic family getaway with stunning beach rentals and gorgeous views. Enjoy serene surroundings while exploring this charming beach town, perfect for outdoor and romantic vacations. With a friendly atmosphere and a blend of recreational activities, you’ll find plenty to unwind and create lasting memories with loved ones. Experience the best of both relaxation and adventure in this beautiful coastal region.

  • Ocean City: Located 6 miles from Ocean Pines, Ocean City is a vibrant coastal city known for its bustling boardwalk and family-friendly atmosphere. Visitors flock to Ocean City for outdoor activities, romantic strolls along the beach, and a variety of attractions that cater to all ages. The iconic boardwalk features shops, restaurants, and amusement parks, while the nearby family beach offers a relaxing spot for sunbathing and swimming. With its lively nightlife and numerous water sports opportunities, Ocean City is a must-visit destination for anyone looking to enjoy the sun and surf.
  • Isle of Wight: Just 3 miles from Ocean Pines, Isle of Wight is a picturesque island that promises outdoor adventure and stunning scenery. This serene locale is perfect for nature lovers and those seeking a peaceful retreat. Visitors can explore its scenic golf courses or spend a day at the family beach, where the natural beauty of the coast is on full display. The nearby nature reserve provides excellent opportunities for hiking, birdwatching, and immersing oneself in the local ecosystem, making Isle of Wight an ideal spot for outdoor enthusiasts.
  • Showell: A charming village located 3 miles from Ocean Pines, Showell offers a delightful blend of outdoor fun and family-oriented activities. Known for its welcoming atmosphere, visitors can enjoy a round of golf at the local course or take a leisurely stroll along the boardwalk. The nearby beach and family beach are perfect for a day of sun and sand, while the national state park invites exploration and adventure. Showell's quaint setting makes it a great choice for those looking to relax 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 simple

Are you aiming to save money on your next adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even more savings. To discover a Vrbo property that aligns with your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Save more with One Key

Plan your group getaway by booking an eligible Vrbo and earn OneKeyCash on your reservation. Being the organizer certainly has its perks. When you join our travel rewards program, One Key, you’ll gain immediate access to exclusive member discounts and the ability to earn and redeem OneKeyCash on qualifying bookings. Sign up today and begin your journey to savings.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform where you can easily plan new trips, resume your previous searches, and manage your travel itinerary. Within this space, you'll find your saved or booked properties neatly organized under categories such as Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/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 approximately 195 available in the area. These properties are typically situated in peaceful neighborhoods, offering spacious layouts that often include multiple bedrooms, fully equipped kitchens, and outdoor spaces like decks or patios for enjoying the pleasant Maryland weather. Additionally, there are about 22 charming cottages available, which provide a cozier atmosphere ideal for couples or small families. Condos, mobile homes, and apartments are also present in several numbers, suiting travelers looking for varied accommodations.
Are there any beach house rentals in Ocean Pines?
In Ocean Pines, Maryland, there are approximately 335 beach house rentals available, making it a popular destination for vacationers. These rentals typically include spacious private homes equipped with multiple bedrooms, fully stocked kitchens, and comfortable living areas, ideal for families and groups. Many properties also feature outdoor spaces such as decks or patios, allowing guests to enjoy the serene surroundings. Ocean Pines is conveniently located near attractions like the Ocean Pines Golf Club and the scenic coastal areas, providing easy access to both leisure and recreational activities. Find your rental near the beach in Ocean Pines.
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 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 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.
What are popular rental amenities in Ocean Pines?
In Ocean Pines, popular rental amenities include fully equipped kitchens, allowing travelers to prepare their own meals. Many rentals also feature shared swimming pools, great for cooling off during warm days. Outdoor spaces such as patios provide a great area for relaxation or dining al fresco. Additionally, properties often come equipped with coffee and tea makers for a quick morning brew, and onsite parking is typically available, making it convenient for guests traveling by car.
Are there any family house rentals in Ocean Pines?
In Ocean Pines, Maryland, there are numerous family-friendly house rentals available, with around 152 options to choose from. This community is well-suited for families, offering spacious properties that often include multiple bedrooms and ample living areas for everyone to gather. Many homes feature practical amenities such as fully equipped kitchens, allowing for easy meal preparation, as well as outdoor spaces for children to play or for barbecues.

The neighborhood is conveniently located near several attractions and points of interest. Visitors can easily access the beautiful beaches of Ocean City, which is just a short drive away, or enjoy the scenic views at nearby parks and recreational areas. See all family-friendly rentals in Ocean Pines.
Can I rent a vacation home with a pool or hot tub in Ocean Pines?
In Ocean Pines, travelers have a wealth of options for renting vacation homes that feature pools and hot tubs, with around 175 properties available that offer swimming pools and an additional 15 that come equipped with hot tubs. This charming community is located near the coast of Maryland and provides a peaceful retreat with easy access to nearby beaches and outdoor activities.

Visitors can expect a variety of amenities in these rentals, including private pools that are superb for relaxing or entertaining, as well as hot tubs that provide a soothing experience after a day of exploration. Many homes also feature spacious outdoor areas, fully equipped kitchens, and comfortable living spaces, making them ideal for families or groups looking to enjoy a memorable getaway. Find your rental in Ocean Pines with a pool or a hot tub.
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 travelers 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.
Are there pet-friendly vacation rentals in Ocean Pines?
In Ocean Pines, there are numerous pet-friendly vacation rentals available, with around 77 options for travelers to choose from. Many of these properties feature spacious layouts, fully equipped kitchens, and outdoor areas such as decks or patios, superb for enjoying the beautiful Maryland weather. Some rentals may also include amenities like hot tubs, community pools, and access to nearby recreational facilities.

The Ocean Pines community is conveniently located near various pet-friendly points of interest. For outdoor activities, the nearby Assateague Island National Seashore offers stunning landscapes and trails where pets are welcome, providing a fantastic opportunity for exploration and adventure. Additionally, the area is home to several local parks and dog-friendly beaches, making it an ideal destination for pet owners looking to enjoy both relaxation and outdoor fun. See all pet-friendly rentals in Ocean Pines.
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. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Ocean Pines for a vacation rental?
July is the most popular time to visit Ocean Pines, Maryland, drawing families and adventure seekers eager for a summer getaway. During the peak season of June through August, visitors can bask in warm temperatures, typically ranging from the mid-70s to low 90s Fahrenheit, superb for beach outings, water sports, and enjoying the local festivals. The vibrant atmosphere is complemented by the close proximity to Atlantic beaches, making it an excellent choice for outdoor activities and sightseeing.

If you're looking for a more budget-friendly option, consider visiting in November. This month, while quieter, offers a unique charm as the summer crowds have dissipated. You can take leisurely strolls along the picturesque coastal paths, explore local shops, or indulge in some post-season tranquility without the hustle and bustle of peak summer traffic.

Ultimately, the best time to visit Ocean Pines depends on your preferences. If you thrive on lively summer energy with various activities, July will be your ideal choice.
Are there any remote work vacation rentals in Ocean Pines?
In Ocean Pines, Maryland, there are numerous options for remote work vacation rentals, with around 200 available throughout the area. This charming community offers a variety of accommodations that cater specifically to working travelers. Many rentals come equipped with essential remote work amenities such as high-speed Wi-Fi, dedicated office spaces with desks and comfortable chairs, and even additional features like computer monitors and safes for securing valuables.

The location itself is serene and peaceful, making it an ideal place for productivity while still being close to local attractions. Within Ocean Pines, you'll find beautiful parks, scenic lakes, and walking trails, providing a relaxing environment to unwind after work hours. Additionally, the nearby coastal town of Ocean City is just a short drive away, offering beaches, dining, and entertainment options for your downtime. 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.
What are the top attractions in Ocean Pines?
In Ocean Pines, visitors can enjoy a range of attractions that cater to both relaxation and recreation. The community is known for its beautiful waterfront properties and access to scenic views of the Assawoman Bay. Nearby, the Ocean Pines Golf and Country Club offers an excellent golfing experience for enthusiasts, while the various parks within the community provide walking trails and picnic areas for families.

For those interested in water activities, the nearby beaches of Ocean City are just a short drive away, where you can enjoy sunbathing, swimming, and various water sports. Additionally, the area hosts several local events and farmers' markets throughout the year, allowing visitors to experience the local culture and community vibe.
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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 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.
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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, 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 organizing 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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