Ocean Pines vacation rentals near the ocean
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Ocean Pines
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Ocean Pines vacation rentals
Ocean Pines condo rentals
Ocean Pines house rentals
Your guide to Ocean Pines
All About Ocean Pines
What started in 1968 as a small resort on Maryland’s Easter Shore has grown into a thriving seaside community with swimming pools, walking trails, a yacht club, and a marina ripe for stand-up paddleboarding, kayaking, and canoeing. Ocean Pines is home to a network of canals that offer direct access to the water for some residents.
At nearby Ocean City, just five miles away, you can stroll the boardwalk or go for a swim along the 10 miles of beaches. Amusement parks offer thrill rides and arcade games, and you can head over to Ocean City Life-Saving Station Museum to learn about the historic role performed by the United States Life-Saving Service. Ocean Pines is also less than 30 minutes away from the stunning Assateague Island, a National Natural Landmark known for its pristine landscapes and wildlife, including white-tailed deer, river otters, and muskrats.
The best time to stay in a vacation rental in Ocean Pines
The Ocean City area is an extremely popular summer destination thanks to the beautiful weather and sandy beaches. Accommodation options may be limited during this time so it is a good idea to book early. Fall and spring tend to be much quieter, and you may find that many of the amenities in Ocean Pines are largely empty on weekdays, as well as the Ocean City Boardwalk and beaches. Ocean City holds its annual Sunfest at the end of September, offering activities like arts and crafts as well as a variety of food.
During the winter, it gets very quiet in Ocean Pines, and many local businesses close for the season. However, this is still a great time to book an Ocean Pines rental as you can explore the nearby beaches and parks in solitude. There is also a farmer’s market held every Saturday to stock up on fresh produce and artisanal products. There are even themed markets for Halloween, Thanksgiving, and Christmas.
Top things to do in Ocean Pines
Twenty minutes outside of town, Assawoman Bay is a lagoon located on the northern end of Baltimore. It is a popular destination for many water activities, including boating and fishing. The most popular catches here are summer flounder, bluefish, and Atlantic stingray.
Located just a short drive from Ocean Pines, Ocean City offers all the bustling activities and attractions of a large resort city. Here, you can visit one of the many amusement parks such as Jolly Roger, watch the sunset on the boardwalk, or grab crab cakes and drinks at one of the local bars and restaurants.
This gorgeous uninhabited island stretched between Virginia and Maryland offers some of the area’s most pristine beaches and natural landscapes, including salt marshes and maritime forests surrounding the island’s stunning bays. It is a great spot for hiking and wildlife viewing and while you are there, you may even be able to see the island’s wild ponies.