Discover a selection of 4,000 vacation rentals in Ocean Pines, MD that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and kitchens. Prices start at $131 per night, and houses and condos are popular options for a stay in Ocean Pines. Either way, you'll find a rental for everyone's needs.
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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

Activities

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.

Weather

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.

How many vacation rentals are available around Ocean Pines, MD?

Our 2020 property listings offer a large selection of 4,111 vacation rentals around Ocean Pines. From 696 house rentals to 2,659 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

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: 1,821 vacation rentals
  • Caine Woods: 849 vacation rentals
  • South Bethany Harbor: 81 vacation rentals
  • Montego Bay: 666 vacation rentals
  • Heron Harbour Isle: 555 vacation rentals

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

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

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

  • Ocean Pines Golf and Country Club: 153 vacation rentals
  • Pine Shore Golf North: 5,409 vacation rentals
  • Assateague Island National Seashore: 5,086 vacation rentals
  • Bethany Beach Boardwalk: 3,302 vacation rentals
  • Bayside Resort Golf Club: 6,833 vacation rentals

But there are many other points of interest around Ocean Pines listed on Vrbo 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. Vrbo has 696 Houses in Ocean Pines. Our other popular types of vacation rentals in Ocean Pines include:

  • Condos/Apartments: 2,659 rentals available
  • Townhouses: 635 rentals available
  • Cabins: 30 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Cottages 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 2,504 vacation rentals with pool available in Ocean Pines. Please use our search bar to access the selection of vacation rentals available.

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