Ocean Pines vacation rentals

We found 7,209 vacation rentals — enter your dates for availability

Discover a selection of 116 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:Jun 12 - Jun 19

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

Berlin

10% off
Price is CA $456
CA $4,255 total
includes taxes & fees
Newley Renovated Beach Home, Min. to Ocean City,1st FL. Master Suite, walk in

Find spaces that suit your style

Find out more about Ocean Pines

Why visit Ocean Pines

  • Scenic Outdoor Activities: Ocean Pines offers stunning ocean views and sandy beaches, perfect for outdoor enthusiasts.
  • Charming Local Atmosphere: Explore nearby towns filled with friendly locals and historical sites that enrich your visit.
  • Golfing Delight: Enjoy a round at the Ocean Pines Golf Club, a highlight for golf lovers.
  • Family-Friendly Fun: Visit nearby amusement parks for exciting activities suitable for all ages.
  • Diverse Accommodation Options: Choose from a range of vacation rentals, including cozy homes and condos.

Popular types of accommodation around Ocean Pines

At Ocean Pines, we offer a diverse selection of vacation rentals that cater to your needs, including houses, condos, and apartments. Whether you're looking for a cozy house in Ocean Pines or a comfortable stay in nearby Ocean City, our platform provides transparent information to help you make the best choice. Enjoy savings and peace of mind as you embark on your Canadian getaway.

  • Houses: A favourite among visitors, these homes offer spacious accommodations ideal for families or groups seeking a home-like atmosphere during their stay in Ocean Pines.
  • Condos: These modern dwellings provide convenient amenities and are perfect for those looking for a blend of comfort and style.
  • Apartments: A practical option for solo travellers or couples, offering all the essentials for a comfortable getaway.
  • Cottages: These quaint retreats offer a charming and intimate atmosphere, perfect for a relaxing escape.
  • Villas: Luxurious and spacious, villas provide an upscale experience for those seeking a bit more indulgence during their stay.**

Top attractions near Ocean Pines

Ocean Pines, Maryland, is a perfect destination for outdoor enthusiasts and couples seeking a beach getaway. With attractions like the Ocean Pines Golf Club and nearby Ocean City Beach, visitors can enjoy a mix of recreation and relaxation. The area offers a variety of experiences, including scenic esplanades and family-friendly amusement parks, making it an ideal spot for cultural adventures and memorable vacations.

  • Ocean City Boardwalk: A vibrant esplanade featuring charming shops, tasty eateries, and fun-filled activities, perfect for couples and families alike. Enjoy romantic strolls or lively outdoor events while soaking in the stunning ocean views.
  • Ocean City Beach: A picturesque sandy beach offering a relaxing atmosphere. Enjoy sunbathing, swimming, or beach sports while listening to the soothing sound of the waves.
  • Jolly Roger Amusement Park: An exciting amusement park filled with thrilling rides and attractions for the whole family. Experience adventure in a fun, outdoor setting that guarantees a memorable day.

Things to do recommended for couples

For a romantic getaway in Ocean Pines, enjoy a round of mini-golf at Maui Golf or Embers Island, both offering fun vibes just 8.0km away. For a unique shopping experience, visit Seacrets, where you can soak up the local atmosphere and explore together.

Things to do recommended for families

Your family will love Northside Park for wellness and relaxation, just 9.7km from Ocean Pines. For adventure, visit Grand Prix Amusements, 6.4km away, or enjoy some fun at the Carousel Ice Skating Rink, also 9.7km from your location. It's a perfect blend of activities.

Things to do recommended for groups

Groups visiting Ocean Pines can enjoy a round of golf at the Bayside Resort Golf Club, indulge in shopping at the Tanger Outlet Center, and explore the Ocean Plaza Mall Shopping Center for a mix of family-friendly and entertaining experiences within a short drive.

*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

When planning your trip, whether you're traveling with friends, family, pets, or seeking extended stays, be sure to apply the appropriate filters based on your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Ocean Pines with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Ocean Pines with young kids: Traveling with young children can present its challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to 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. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties offer feeding bowls and cozy beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Ocean Pines: If you're in search of vacation rentals that offer discounts 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 accommodations. Don’t forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Ocean Pines

Ocean Pines, Maryland, offers a delightful blend of outdoor adventures and romantic beach getaways. With its stunning ocean views and sandy beaches, this family-friendly community is perfect for relaxation and recreation. Explore the charming nearby towns and immerse yourself in the local atmosphere, where friendly people and historical sites await. Whether you're seeking a vacation rental or a peaceful retreat, Ocean Pines has something for everyone looking to enjoy the beauty of the Eastern Shore.

  • Ocean City: Located a mere 9.7km from Ocean Pines, Ocean City is a bustling seaside resort renowned for its vibrant boardwalk and family-friendly attractions. This lively city offers a delightful mix of outdoor activities, romantic spots, and family adventures. Stroll along the boardwalk lined with shops and eateries, or spend a day at the water park for some thrilling fun. With beautiful beaches and the scenic esplanade nearby, Ocean City is perfect for those looking to soak up the sun and enjoy a lively atmosphere.
  • Isle of Wight: Situated 4.8km from Ocean Pines, Isle of Wight is an idyllic island offering stunning natural beauty and outdoor adventures. This charming area is ideal for those seeking scenic views and a touch of adventure. Golf enthusiasts can enjoy a round at the local golf course, while nature lovers can explore the serene nature reserve. With family-friendly beaches and picturesque landscapes, Isle of Wight is a fantastic spot for relaxation and outdoor exploration, making it a must-visit destination during your stay.
  • Glen Riddle: Just 4.8km from Ocean Pines, Glen Riddle is a quaint neighborhood that combines outdoor recreation with a romantic atmosphere. This charming area offers access to golf courses and beautiful beaches, perfect for families and couples alike. Visitors can enjoy a leisurely day at the beach or explore the nearby esplanade. Glen Riddle's inviting environment and array of activities, including its proximity to the boardwalk, make it a delightful place for those looking to unwind 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 a breeze

Are you hoping to save on your upcoming adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay to enjoy substantial savings. To discover a Vrbo property that aligns with your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a user-friendly platform where you can craft new trips, continue from where you paused, or manage your existing plans. You'll find your saved or booked properties neatly organized under Potential, Upcoming, or Current Trips. To begin utilizing Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

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 travelling 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.
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.
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 travellers 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 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. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Ocean Pines for a vacation 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 vacation 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.
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 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.
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 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 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, Vrbo 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 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.

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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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