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Ocean Pines vacation rentals near the ocean

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Top-rated vacation rentals in Ocean Pines

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Home in Ocean Pines
Peaceful Pines: 3 Bedroom Home with Coastal Charm
Enjoy a stay away from the crowds of OCMD in the family friendly location of Ocean Pines. Only 8 miles away from the beaches in OC and 15 miles away from Assateague. There is a boat/kayak launch with free parking only 3 minutes around the corner. Play at the playground/soccer field across the street or take a longer walk to the playground at White Horse Park. Visit OP Beach Club, spend the day at one of the 5 community pools, or enjoy a round of golf. Peaceful Pines has so much to offer!
$169 per night
Home in Ocean Pines
Nottingham Beach Retreat
PERSONAL RESERVATION SPECIALIST AVAILABLE 24/7 FREE LINENS & TOWELS PROVIDED! Welcome to our newly renovated beach home in the premiere residential community of Ocean Pines! Not only are we a short 12-minute ride into the resort town of Ocean City but here you have access to private community amenities, multiple pools open year-round, yacht club, state-of-the-art golf courses, and much more!
$100 per night
Home in Ocean Pines
Cozy home in Ocean Pines
Relax with the whole family at this peaceful place to stay, just 10 minutes away from Ocean City Beach.
$129 per night

Stay near Ocean Pines's top sights

Ocean Pines Yacht Club & Marina28 locals recommend
Abi's Diner4 locals recommend
Southgate Grill14 locals recommend
DeNovo's Trattoria8 locals recommend
Plaza Tapatia5 locals recommend
A Bagel And ...14 locals recommend

Ocean Pines vacation rentals

Home in Ocean Pines
Snowbird Bay Cottage
$92 per night
Home in Ocean Pines
*Catch Me By The Sea*
$216 per night
Home in Ocean Pines
Family Friendly Beach Home
$150 per night
Condo in Berlin
Waterfront on Gum Point Rd - Coral Tides Suite
$165 per night

Ocean Pines condo rentals

Condo in Ocean City
Oceanfront 1 Bedroom-Sleeps 6-Outdoor TV-King Bed
$112 per night
Condo in Ocean City
Oceanfront 1 Bedroom-Sleeps 4-Balcony-Laundry-WiFi
$109 per night
Condo in Ocean City
Oceanfront Studio Sleeps 4-Fireplace Pool Laundry
$100 per night
Condo in Ocean City
Oceanfront Studio-Sleeps 4-Balcony-Fireplace-WiFi
$119 per night

Ocean Pines house rentals

Home in Ocean Pines
Charming 2BR Dog Friendly | Pool | Fireplace
$74 per night
Home in Ocean Pines
Ocean Pines Home Away From Home
$187 per night
Home in Ocean Pines
Beachin' it in Ocean Pines
$144 per night
Home in Ocean Pines
Serene OP cottage perfect for your next getaway!
$200 per night

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.

  1. Airbnb
  2. United States
  3. Maryland
  4. Worcester County
  5. Ocean Pines