Ocean Pines vacation rentals

We found 7,305 vacation rentals — enter your dates for availability

Select from 209 homes, 22 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:Aug 22 - Aug 29
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Find out more about Ocean Pines

Find out more about Ocean Pines

Why visit Ocean Pines

  1. Beautiful Beaches: Enjoy the stunning coastline and sandy shores of nearby Ocean City.
  2. Outdoor Activities: Explore scenic parks and indulge in hiking, biking, and water sports.
  3. Charming Neighborhoods: Discover unique architecture and picturesque homes throughout Ocean Pines.
  4. Family-Friendly Fun: Engage in activities suitable for all ages, ensuring memorable experiences for families.
  5. Cozy Accommodations: Choose from a variety of vacation rentals, from condos to lakefront homes.

Popular types of accommodation around Ocean Pines

If you're exploring vacation rentals in Ocean Pines, you're in for a treat! The most popular options include cozy condos, spacious apartments, and houses. Whether you're seeking an oceanfront escape, a charming Ocean City cottage, or a lakefront getaway, our diverse selection has something for everyone. Enjoy the luxury of a pool or the comfort of a spacious home—your perfect vacation awaits in Ocean Pines!

  • Condos: The top choice for vacationers in Ocean Pines, offering modern amenities and convenient access to local attractions.
  • Apartments: A popular option for travelers seeking comfortable and spacious living arrangements during their stay.
  • Houses: Ideal for families or groups looking for a home-like experience with added privacy and flexibility.
  • Cottages: Charming and cozy, these rentals provide a quaint escape close to nature.
  • Villas: Luxurious accommodations that cater to those desiring upscale amenities and beautiful surroundings.**

Top attractions around Ocean Pines

Ocean Pines, located in Berlin, Maryland, is the perfect destination for outdoor enthusiasts, families, and couples seeking a romantic getaway. Explore the beautiful beaches, scenic esplanades, and nearby state parks that offer a blend of culture and nature. Don’t miss the chance to view stunning houses in the area, enhancing your experience in this charming locale. Whether you're looking for adventure or relaxation, Ocean Pines has something for everyone.

  1. Ocean City Boardwalk: A vibrant 3-mile esplanade filled with family-friendly attractions, shops, and restaurants. Enjoy the lively atmosphere, take a romantic stroll, or indulge in delicious local treats while soaking in the outdoor vibes.
  2. Ocean City Beach: A beautiful sandy beach perfect for sunbathing, swimming, and beach games. Experience the relaxed beach vibes while enjoying stunning ocean views and refreshing breezes.
  3. Roland E. Powell Convention Center: A premier event venue hosting conferences, conventions, and entertainment events. Its business vibes make it an ideal spot for networking and experiencing local culture.

Things to do recommended for couples

Discover romance in Ocean Pines with a round of golf at the luxurious Ocean Pines Golf and Country Club. Enjoy a fun mini-golf adventure at Maui Golf, or savor exquisite wines at Costa Ventosa Vineyard and Winery, perfect for an unforgettable couple's experience.

Things to do recommended for families

Families visiting Ocean Pines will love Northside Park for its serene recreation, the Carousel Ice Skating Rink for thrilling ice skating fun, and Frontier Town Water Park and Golf for a splash of adventure. Each offers unique experiences just a short drive away.

Things to do recommended for groups

Experience the thrill of gaming at the Casino at Ocean Downs, just 3 miles from Ocean Pines. Enjoy entertainment and romance at Seacrets Distilling Company, 5 miles away, or hit the greens at Bayside Resort Golf Club, also 5 miles away, for some outdoor fun!

What do I need to keep in mind when booking a vacation around Ocean Pines

When planning your trip—whether you're traveling with a group, family, pets, or seeking extended stays—be sure to prioritize your preferences with the right filters. Here are some helpful Vrbo booking tips to guide 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 apply filters for these options and more on Vrbo.
  • Traveling to Ocean Pines with young kids: Traveling with young kids can be quite a challenge. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can enhance your travel experience.
  • Taking your pets with you to Ocean Pines: For many families, a vacation wouldn't be the same without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly homes come equipped with feeding bowls and beds, ensuring that both you and your pets feel completely at home.
  • Planning for a long term stay visiting Ocean Pines: If you're in search of vacation rentals that offer special rates for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay around Ocean Pines

Discover the charm of Ocean Pines, Maryland, where outdoor adventures meet family-friendly fun. Explore nearby Ocean City for stunning ocean views and a vibrant atmosphere perfect for singles and couples alike. Enjoy the scenic Eastern Shore, unwind by the waterfront, and immerse yourself in the rich history of the area. Whether you're seeking relaxation or excitement, Ocean Pines offers an ideal vacation experience for everyone.

  • Ocean City: Located approximately 6 miles from Ocean Pines, Ocean City is a bustling resort town renowned for its vibrant boardwalk, which stretches for miles along the Atlantic coast. This lively destination is perfect for outdoor enthusiasts and families alike, offering a plethora of activities such as water parks, shopping, and dining options. Notable attractions include the picturesque beach where you can soak up the sun, and the iconic esplanade, perfect for leisurely walks. With its combination of romance and family-friendly fun, Ocean City is a must-visit for any traveler.
  • Showell: Just 3 miles away from Ocean Pines, Showell offers a charming and tranquil escape for visitors searching for outdoor adventures and family activities. Known for its beautiful golf courses and picturesque parks, Showell is ideal for a leisurely day on the green or a fun-filled family outing. With attractions such as nearby beaches providing opportunities for sunbathing and swimming, Showell's friendly atmosphere makes it a great spot for both relaxation and recreation.
  • Glen Riddle: Glen Riddle, located a mere 3 miles from Ocean Pines, is a delightful neighborhood that combines outdoor activities with romantic settings. With access to premier golf courses and scenic boardwalks, Glen Riddle invites visitors to savor the beauty of its lush landscapes. Enjoy a day at the beach or take a stroll on the esplanade, where scenic views meet family-friendly fun. This neighborhood is an excellent choice for those looking to unwind while still enjoying a variety of attractions.

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 SunnyAverageModerately Low
February40.1°F (4.5°C)Light RainMostly SunnyAverageModerately Low
March45.3°F (7.4°C)Light RainMostly SunnyAverageAverage
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 SunnyHighModerately High
July77.5°F (25.3°C)Light RainMostly SunnyHighModerately High
August76.3°F (24.6°C)Light RainMostly SunnyHighModerately 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 SunnyLowModerately Low

Booking with Vrbo is simple

Are you hoping to cut costs on your next getaway? Being flexible with your travel dates can really make a difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that meets your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect spot for your trip!

Save more with One Key

Plan your group trip by booking an eligible Vrbo and earn OneKeyCash™ on your entire reservation. Being the planner truly has its rewards! When you join our travel rewards program, OneKey, you'll gain access to exclusive discounts and accumulate OneKeyCash™ on qualifying bookings. Sign up today and start enjoying the savings right away!

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient space for you to plan new adventures, manage your travel arrangements, and keep track of your bookings. Your saved or reserved properties are neatly organized into categories: Potential, Upcoming, and Current Trips. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Ocean Pines?
Based on our data, cottages are the most popular type of vacation property in Ocean Pines. But as you’d expect, everyone’s idea of an epic trip is bound to be different. Vrbo has vacation rentals of all sizes and shapes, and we’ll help you discover the perfect fit.
How much does it cost to rent a vacation rental in Ocean Pines?
The average price for a vacation rental in Ocean Pines depends on several factors, including length of stay, property type and season. Whether you’re thinking about a sprawling villa with space for the whole family or a quaint cabin for just you and the kids, just add your travel dates to find stays with unbeatable value.
How much does it cost to rent a beach house in Ocean Pines?
Prices for beach houses in Ocean Pines can differ depending on the type and size of the property and when you’re traveling. Simply enter your travel dates into Vrbo and how many guests to view your rental options and prices. From there you can use our filters to narrow your search by ratings, amenities and more.
Are there pet-friendly vacation rentals in Ocean Pines?
Yes. You’ll have a choice of 194 vacation rentals that cater to pets in Ocean Pines. Some of our pet-friendly vacation rentals have a backyard for your four-legged friend to play around in, complimentary treats, doggie beds and proximity to parks or green space. Apply the “Pets allowed” filter to find a vacation home on Vrbo that’s pawfect.
Can I rent a house with a pool in Ocean Pines?
Check the “pool” box in our filter tool and you can choose from 137 houses with private pools in Ocean Pines on Vrbo. Morning swim, afternoon splash or midnight soak? How you spend your leisure time is up to you when your vacation home comes with its own pool.
What are popular rental amenities in Ocean Pines?
The most popular rental amenities people are looking for in Ocean Pines are a nearby waterfront, a lake view and an ocean view. Whether you’re on a trip with family, friends or even pets, Vrbo vacation rentals come with the best amenities for fun and relaxation with the people closest to you.
Are there large group vacation rentals in Ocean Pines?
With 52 vacation rentals that can sleep 10 or more guests in Ocean Pines, you don’t have to leave anyone off your guest list. From extended family vacations to events like Christmas and birthday parties, Vrbo can help you find a large group rental that fits the occasion.
Are there vacation rentals in Ocean Pines that welcome kids?
Ocean Pines has 193 family-friendly vacation homes to pick from. And tracking down a stay that welcomes youngsters is simple with Vrbo’s “Properties good for families” filter. On top of having the whole place to yourselves, you’ll have access to amenities and perks like dining rooms, private pools and yards.
What are the top attractions for families in Ocean Pines?
Treat the kids to a good time at these fantastic family-friendly attractions in Ocean Pines:

  • Ocean Pines Golf and Country Club
  • River Run Golf Club

Are there one-bedroom vacation rentals in Ocean Pines?
Yes, there are three one-bedroom properties in Ocean Pines to select from. A one-bedroom vacation property is a great choice if it’s just you and your partner or if you’re flying solo. Toss in more privacy, convenience and space than a standard hotel, and you’ve got the makings of a memorable trip.
Can I find two-bedroom vacation rentals in Ocean Pines?
Ocean Pines has 18 two-bedroom properties to select from. Book a vacation home with all the comfort and privacy you want at a price that’s hard to resist on Vrbo.
Are there vacation rentals with WiFi in Ocean Pines?
Ocean Pines has 48 vacation rentals with WiFi, so you can stay connected while you’re traveling. Simply check the “WiFi” box in our handy search filter to find the perfect property. From streaming movies with your family to writing and sending emails, these Vrbo homes make it a breeze to go online.
How can I find vacation rentals with air conditioning in Ocean Pines?
Ocean Pines has 186 vacation rentals where you can kick back in air-conditioned comfort. To book a stay on Vrbo that features this amenity, enter your travel dates and use the filters to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Ocean Pines?
Age restrictions can vary across properties on Vrbo, so double-check the rules of the vacation home in Ocean Pines you want to book. But typically, it’s 16, 18 or 21.
How long can I rent a vacation rental in Ocean Pines for?
The length of time you can book a vacation rental in Ocean Pines depends on the property. Just enter your chosen travel dates to view a list of options offering extended stays. With lots of amenities like air conditioning and full kitchens, as well as some offering discounted weekly or monthly prices, you’re sure to find the perfect place to call your home away from home in Ocean Pines.
Does Vrbo offer discounts for vacation homes in Ocean Pines?
On Vrbo, we’ve got plenty of fantastic discounts and bargains for Ocean Pines. Check out our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you’re off on a weekend retreat or a longer stay, Vrbo offers options for all budgets and styles.

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