
Vacation rentals in Ocean Pines
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Top-rated vacation rentals in Ocean Pines
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Vacation rentals for every style
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Popular amenities for Ocean Pines vacation rentals
Ocean Pines vacation rentals near the ocean

Mid OC Bayside Canal Condo Remodeled-Pets Welcome!

The Purple Pad - Ocean City MD beach block cottage

Harbour Sails #304 Spectacular Waterfront Suite

Clean & New, Balcony With a View

Steps to Ocean! Uncrowded Beach. Midtown Retreat

Gorgeous New Beachfront! King Bed, Direct Sea View

GREAT LOCATION! Remodeled 1BR condo w/ Bay View!

Ocean Block with Ocean Views | Steps to the Beach!
Ocean Pines house rentals

Cozy home in Ocean Pines

Ocean Pines 2BR 1BA Cottage with Fire Pit

Salty Serenity

Watertown 104 with OCP Beach Passes

Little house in Berlin, Md.

Private, pet-friendly, w/game room & new kitchen

Serene OP cottage perfect for families!

Ocean City (OC) Beach Retreat
Ocean Pines homes near the ocean

Beach House on the MD-DE Border of Ocean City!

Beautiful, bright & steps to the beach

Beautiful 4 bd/3.5 ba Rehoboth Beach House

Seas The Bay on the Waterfront!

Walk to Everything, Fully Stocked, sleeps 10

Bay Dreamin; Townhouse steps to Beach & Boardwalk!

Private pool in BayVista! 4bdrm family beach house

New list 2024- Bethany Beach House- 3 bed, 2 bath
Quick stats about vacation rentals in Ocean Pines
Total rentals
300 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
7.8K reviews
Family-friendly rentals
280 properties are a good fit for families
Pet-friendly rentals
90 properties allow pets
Rentals with a pool
160 properties have a pool
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
Assawoman Bay
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.
Ocean City
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.
Assateague Island
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.
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Ocean Pines?
Yes! Work meets play with ease at over 140 vacation rentals in Ocean Pines featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Ocean Pines?
Four-legged friends are welcome in Ocean Pines. Choose from more than 90 vacation rentals for guests traveling with pets.
Are there Ocean Pines vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 160 vacation homes with pools in Ocean Pines, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in townhouse rentals in Ocean Pines?
Experience the best of Ocean Pines with our townhouse rentals, starting at about $130 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Ocean Pines have a bbq area?
Absolutely! We offer over 60 house rentals with a bbq area in Ocean Pines. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Ocean Pines have a gym?
Absolutely! We offer over 20 house rentals with a gym in Ocean Pines. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Ocean Pines have self check-in?
Absolutely! We offer over 70 house rentals with self check-in in Ocean Pines. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Ocean Pines?
Ocean Pines has more than 240 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
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- Ocean City Beach
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- Cape Henlopen State Park
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