Ocean Pines vacation rentals

We found 7,140 vacation rentals — enter your dates for availability

Discover a selection of 105 homes and other vacation rentals in Ocean Pines that are 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:May 15 - May 22

Image gallery for Newley Renovated Beach Home, Min. to Ocean City,1st FL. Master Suite, walk in

Interior
10 out of 10, Exceptional, (23 reviews)
Exceptional
(23 reviews)

Newley Renovated Beach Home, Min. to Ocean City,1st FL. Master Suite, walk in

Ocean Pines

8% off
Price is $409
$2,860 for 7 nights
All fees included
Newley Renovated Beach Home, Min. to Ocean City,1st FL. Master Suite, walk in

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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 prevalent rental option, with about 174 available throughout the community. These properties typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups looking for comfort and convenience. Many houses also include outdoor spaces such as decks or patios, superb for enjoying the pleasant Maryland weather. Additionally, there are around 20 cottages, which offer a charming, cozy alternative for those seeking a more intimate stay.
Are there any beach house rentals in Ocean Pines?
In Ocean Pines, there are approximately 263 beach house vacation rentals available, making it a popular destination for travelers. These rentals are primarily located in peaceful neighborhoods, providing a relaxing atmosphere away from the hustle and bustle. Travelers can expect a variety of amenities, including fully equipped kitchens for home cooking, spacious living areas for gathering, and outdoor decks or patios for enjoying the pleasant coastal climate. Many properties also feature multiple bedrooms, which are ideal for families or larger groups.
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 vacation rental amenities include fully equipped kitchens, allowing guests to prepare their own meals conveniently. Many rentals also feature coffee and tea makers, ideal for those who enjoy a warm beverage in the morning. Onsite parking is a common amenity, providing easy access for travelers with vehicles. Additionally, many properties offer outdoor spaces such as decks or patios, superb for relaxing and enjoying the pleasant Maryland weather.
Can I find family house rentals in Ocean Pines?
In Ocean Pines, Maryland, there are numerous family-friendly house rentals available—specifically around 137 options to choose from. This community is well-suited for families, with spacious homes that often include multiple bedrooms, inviting living areas, and outdoor spaces for kids to enjoy. Many properties come equipped with full kitchens, allowing families to prepare meals together, as well as amenities such as Wi-Fi and air conditioning for added comfort.

The location is ideal for families looking to explore nearby attractions. Visitors can easily access the beaches of Ocean City, just a short drive away, where fun in the sun awaits. Additionally, the community has its own amenities, including parks, pools, and recreational facilities, ensuring that there's plenty to do right at your doorstep.
Can I rent a vacation home with a pool or hot tub in Ocean Pines?
In Ocean Pines, there are plenty of vacation homes available for rent that feature pools and hot tubs, with around 152 options for properties with pools and 13 that include hot tubs. This charming coastal community offers a variety of neighborhoods where these rentals can be found, including the serene areas near the marina and the more vibrant sections close to local amenities and recreational facilities.

Travelers can expect a range of amenities in these vacation homes, including private pools, relaxing hot tubs, spacious outdoor areas for gatherings, and fully equipped kitchens ideal for preparing meals. Many properties also have features such as outdoor dining spaces, barbecue grills, and easy access to nearby beaches, enhancing the overall enjoyment of a getaway in this picturesque setting.
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.
Can I book pet-friendly vacation rentals in Ocean Pines?
Yes, you can book pet-friendly vacation rentals in Ocean Pines, where there are approximately 72 options available to choose from. This community, located near the scenic shores of the Atlantic Ocean, offers a variety of properties that cater to travelers with pets. Many of these rentals come equipped with amenities such as spacious backyards, outdoor decks, and fully stocked kitchens, providing a comfortable home base for your stay.

In addition to the vacation rentals, Ocean Pines is conveniently located near several pet-friendly points of interest. The nearby beaches, particularly in the Ocean City area, welcome pets during certain times of the year, allowing for enjoyable beach outings. Additionally, the community features parks and walking trails that are great for daily strolls with your furry companions.
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, as families and beach enthusiasts flock to the area for sun-soaked days and a vibrant setting. The peak season extends from June to August, characterized by a lively blend of outdoor activities, including water sports, beach outings, and local festivals. Visitors can expect warm temperatures, typically ranging from the mid-70s to low 90s Fahrenheit, great for enjoying the beautiful coastal scenery and the nearby beaches.

During these summer months, Ocean Pines offers an array of activities, from kayaking in the tranquil waters to exploring the local nature trails. The community buzzes with energy, making it an ideal time for those seeking camaraderie and dynamic experiences.

For travelers looking for a more budget-friendly option, consider visiting in November. This month provides a quieter atmosphere while still allowing for enjoyable walks along the beach and the opportunity to appreciate the region's natural beauty without the summer crowds.

Ultimately, the best time for you to book a vacation rental in Ocean Pines depends on your preference for lively summer adventures or a more peaceful retreat in the off-season.
Are there any remote work vacation rentals in Ocean Pines?
In Ocean Pines, Maryland, travelers will find a substantial selection of remote work-friendly vacation rentals, with around 181 options available. This community offers a tranquil environment along the picturesque coastal region, making it an attractive choice for those looking to balance work and leisure. Many of the rentals come equipped with essential amenities such as high-speed Wi-Fi and dedicated workspaces, ensuring a productive atmosphere.

The area is known for its proximity to various recreational activities, including boating, fishing, and beautiful beaches. Rentals often feature comfortable living areas, full kitchens for meal preparation, and outdoor spaces ideal for relaxation or taking breaks during the workday. 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, Maryland, United States of America?
In Ocean Pines, visitors can enjoy a range of attractions that highlight the area's natural beauty and recreational opportunities. The community is known for its picturesque waterfront views and access to several lakes, making it ideal for fishing, kayaking, and paddleboarding. The nearby Ocean Pines Golf Club offers a well-maintained course for golf enthusiasts, while the community center hosts various events and activities throughout the year.

For those looking to relax, the nearby beaches, such as Ocean City, are just a short drive away, providing opportunities for sunbathing, swimming, and beachside dining. The area also features several parks and nature trails, superb for walking, biking, or simply enjoying the outdoors.
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.

Frequently asked questions

Are there vacation rentals in Ocean Pines?
Yes, there are vacation rentals close to top local attractions in Ocean Pines, or you can select a secluded option if you're looking for a relaxing stay. Ocean Pines is known for its seaside and live music.
How many vacation rentals are there in Ocean Pines?
With 105 Expedia vacation rentals, you're sure to find just the right place for your Ocean Pines stay.
What can I see and do in Ocean Pines?
While exploring the area, visit family-friendly sights like Jolly Roger Amusement Park, or get outside and enjoy nature at Isle of Wight Bay. Other places in town to visit include Ocean Pines Golf and Country Club and River Run Golf Club.
What are vacation rentals like in Ocean Pines?
Vacation rentals are private properties you can book for a couple of days or more in Ocean Pines. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for families.

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