Destination guide

Ocean Pines: a peaceful community with first-class amenities

Situated on Maryland’s picturesque Eastern Shore, Ocean Pines is a peaceful gated community nestled on nearly 3500 shaded acres. With all the amenities of a modern town, this self-contained enclave offers visitors the opportunity to play a round of golf, hit the hiking trails, or kick back at the yacht club. You’ll find a range of dining options, and at only 10 miles from bustling Ocean City, an Ocean Pines vacation rental will put you within reach of one of America’s classic beach destinations.

Things to do

Trails and trattorias: attractions in Ocean Pines

With towering pines, sparkling waters, and verdant hills, Ocean Pines is a pleasure to explore, and an amble around the walking trails is a great way to spend a summer morning. Any visit should include a round of golf on the 18-hole, Robert Trent Jones-designed golf course, while foodies will find a range of dining options ranging from seafood restaurants and crab shacks, to trattorias and family-friendly eateries. An Ocean Pines vacation rental is also only a 20-minute drive from Ocean City, where you can stroll the iconic 3-mile boardwalk, catch a concert, and charter a fishing boat. Crisp falls and crabbing weather: Ocean Pines’ seasons


Ocean Pines offers action-packed days and tranquil nights

An Ocean Pines vacation rental offers the perfect combination of long, relaxing days and peaceful nights. Kick-start your morning with a swim in one of 5 pools, including a heated indoor pool, and while away an afternoon with a game of basketball, or kayak out to Isle of Wight Bay. The yacht club not only offers mooring, but a restaurant with seasonal live music. There’s even a year-round farmers market if you want to prepare an Eastern Shore-inspired feast—think fresh crab cakes, huckleberry pudding, and avocado salad.


Crisp falls and crabbing weather: Ocean Pines’ seasons

July and August are the hottest months in Ocean Pines, with average highs in the mid- to upper 80s. Winters are cool, with average lows between 28 and 30, and average highs reaching 47 in January. The peak time to visit is between Memorial Day and Labor Day; this is when local crabbing is at its best and nearby Ocean City is at its liveliest. Rain is evenly distributed across the seasons, and the area experiences occasional snowfall in January and February, although it’s less than the national average.

Natural features

Ocean Pines offers easy access to the bay and the beach

Ocean Pines is set on Maryland’s Eastern Shore, in Northern Worcester County. It covers nearly 3500 acres, and is peppered with pine trees and shaded walking trails. The marina provides access to Isle of Wight Bay, where you can fish for flounder, tautog, and Atlantic croaker. Ocean City is less than a 20-minute drive from Ocean Pines, and is one of the Eastern seaboard’s most popular beach destinations. Alternatively, take a trip to Assateague Island, where you can wander through the lush pine forests and watch wild ponies on the beach.

How to get there

Traveling to and around Ocean Pines

The nearest airport is in Ocean City, MD (OCE-Ocean City Municipal), located 5.4 mi (8.8 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional), which is 19.5 mi (31.4 km) away.

Where to stay around Ocean Pines?

Our 2019 property listings offer a large selection of 4,260 vacation rentals near Ocean Pines. From 741 Houses to 2,724 Condos/Apartments, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Ocean Pines for a holiday or a weekend are on HomeAway.

What is the best area to stay when traveling to Ocean Pines?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Ocean Pines:

  • Midtown Ocean City: 1,904 vacation rentals
  • Sunset Island: 188 vacation rentals
  • Caine Woods: 851 vacation rentals
  • Montego Bay: 645 vacation rentals
  • Tower Shores: 85 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular points of interest near where I can stay when traveling to Ocean Pines?

HomeAway offers a large selection of vacation rentals near lovely places in Ocean Pines. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Ocean Pines Golf and Country Club: 165 vacation rentals
  • Bethany Beach Boardwalk: 3,407 vacation rentals
  • Assateague Island National Seashore: 5,305 vacation rentals
  • Delaware Seashore State Park: 7,169 vacation rentals
  • Bayside Resort Golf Club: 7,080 vacation rentals

But there are many other points of interest around Ocean Pines listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Ocean Pines?

Yes, of course. HomeAway has 741 Houses in Ocean Pines. Our other popular types of vacation rentals in Ocean Pines include:

  • Condos/Apartments: 2,724 rentals available
  • Cottages: 37 rentals available
  • Townhouses: 681 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Villas and more.

Can I find a vacation rental with pool in Ocean Pines?

Yes, you can select your preferred vacation rental with pool among our 2,693 vacation rentals with pool available in Ocean Pines. Please use our search bar to access the selection of vacation rentals available.

    Explore destinations around Ocean Pines

    Ocean City
    5,443 vacation rentals
    Rehoboth Beach
    3,438 vacation rentals
    Bethany Beach
    6,192 vacation rentals
    Fenwick Island
    5,504 vacation rentals
    3,335 vacation rentals
    Ocean View
    2,258 vacation rentals
    3,011 vacation rentals
    4,045 vacation rentals
    South Bethany Beach
    3,479 vacation rentals
    2,723 vacation rentals
    5,602 vacation rentals
    West Ocean City
    3,841 vacation rentals
    Tower Shores
    85 vacation rentals
    1,700 vacation rentals
    6,258 vacation rentals
    4,676 vacation rentals
    Angola by the Bay
    2,001 vacation rentals
    Long Neck
    388 vacation rentals
    3,761 vacation rentals
    Pocomoke City
    213 vacation rentals