Discover a selection of 6,000 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 private pools. Prices start at $95 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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Top rated rentals — Ocean Pines
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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.

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.

What are the top vacation rentals in or near Ocean Pines?

Whatever your getaway needs, you'll find a rental in or around Ocean Pines that's right up your alley. These are some of our top picks:

  • "Recovery Room Offers A Private Pool And Hot Tub Rental License # 1993" is a hit with guests. Around 1 mile from Ocean Pines, it has 2 bedrooms and loads of handy amenities, including air conditioning and a computer monitor.
  • Another great option is "Family Fun 6br, 4ba, 5 Pools, Linens Available At Cost", which is around 1 mile from Ocean Pines. Featuring 6 bedrooms, a nearby hospital and a dishwasher, it has everything you need to make your stay comfortable.

For even more great options, use the search bar at the top of the page to find the perfect Ocean Pines vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Ocean Pines?

Clock off on Friday afternoon and then forget all about work. If you're up for some relaxation and fun, these properties in and around Ocean Pines promise the perfect weekend getaway:

  • Leave the hustle and bustle behind at "Pet Friendly / Must Be 25 To Rent", which is around 1 mile to the north of central Ocean Pines. There's plenty of adventure and nature to keep you occupied here. Try parasailing and cycling or simply explore the sights of Sunset Park and Furnace Town Living Hertiage Museum.
  • "New Sfh, Close To Beaches, Golf" is another great property to consider. Around 1 mile northwest of Ocean Pines, use it as a base to try some cycling or surfing and boogie boarding. Sunset Park and Assawoman Bay should also be on your itinerary while you're here.

Can I find studio apartments for rent in and around Ocean Pines?

Studio apartments may be small, but they pack a mighty punch when it comes to location and convenience. Throw your bags down at one of these popular studio apartments in and around Ocean Pines:

  • After a fun-filled day of urban exploration, enjoy peace, quiet and privacy at "On Main Street - Apartment - B". Nearby hunting activities and a stovetop are among the useful amenities you'll find here.
  • Another great property is "On Main Street - Apartment - C". Don't let its modest size fool you — this comfy apartment is filled with useful amenities like a stovetop, a nearby beach and plenty more.

Can I find short term rentals in or near Ocean Pines?

Short-term rentals are in good supply in and around Ocean Pines. Stay for a night or two in a penthouse, a budget studio apartment or a roomy home. Whatever sort of vacation rental you're after, you'll have plenty to choose from with Vrbo. These are some of our faves:

  • "Private And Pet - Friendly In Op" is close to the center of Ocean Pines, which means there are plenty of things to keep you entertained. Check out well-known attractions like Casino at Ocean Downs and Main Street Berlin when you're not kicking back in your cozy property.
  • Wake up, enjoy a coffee and then plan what to explore around "Updated 3 Bedroom 2 Bathroom Home". Calvin B. Taylor House Museum and Frontier Town Water Park and Golf are must-do's if you choose to stay at this vacation rental.

What are the best large group vacation rentals in or near Ocean Pines?

Sneak a peek at these large group vacation rentals in or near Ocean Pines and don't worry about leaving anyone off your guest list:

  • You'll have loads of room to move at "Family Fun 6br, 4ba, 5 Pools, Private Ocean Beach Club". Around 1 mile northeast of Ocean Pines, this impressive retreat has 6 bedrooms and sleeps up to 12 guests. Amenities include a water view and a swimming pool.
  • "Modern Home With Central Ac, Free Wifi" is another excellent option. It's around 1 mile to the southeast of Ocean Pines, has 4 bedrooms and welcomes up to 12 guests. A kitchen and a water park are among the things designed to make your stay more comfortable.

Are there large vacation rentals that sleep 30 or more in or near Ocean Pines?

Whether you're planning a birthday party, a wedding or a getaway with friends and loved ones, we can help you find the ideal space for your group. Send invites out to your posse and take a look at these large vacation rentals in or around Ocean Pines:

  • "Almost Hooked - 4 Bedrooms, 2 Bathrooms": The more people you bring the merrier to this sought-after vacation rental. It has 4 bedrooms, accommodates up to 99 people and features loads of amenities, such as a kitchen and a nearby waterfront.
  • "Butt's Cottage - 3 Bedrooms, 2 Bathrooms": Offering the trifecta of space, privacy and comfort, this attractive property can fit up to 99 people in its 3 bedrooms. A kitchen and an oven are among the features that'll help keep your gang comfortable and content.

What are the best houses for rent with a pool in or near Ocean Pines?

From boisterous games of tag to quiet morning dips, a pool promises loads of fun for all ages. Earn brownie points with family or friends by booking a house with a place to swim in or near Ocean Pines:

  • Make every day a pool day at "New Delightful House With Fire Pit And Community Pool". A toaster and a dishwasher are a few of the other amenities that help make this place a favorite.
  • Another popular option is "Ocean Pines House With Screened - In Deck And Grill". There's loads to love about this retreat apart from its pool, such as a fridge and coffee and tea making facilities.

What are the best large family vacation rentals in or near Ocean Pines?

The first mission of any great family trip is finding the perfect place to stay. Whether you're organizing a fun escape with the kids or a multi-generational getaway with relatives, we've got large family vacation rentals in and around Ocean Pines with plenty of space for everyone. Here are a couple of popular options that would love to welcome you:

  • About 1 mile to the northeast of Ocean Pines, "Family Fun 6br, 4ba, 5 Pools, Private Ocean Beach Club" has 6 bedrooms that sleep as many as 12 guests. Amenities here include a microwave oven and a fridge.
  • "Private And Pet - Friendly In Op", around 1 mile to the north of central Ocean Pines, is also perfect for family gatherings. As many as 8 of your nearest and dearest can fit into this spacious rental which offers 3 bedrooms, towels, a smart TV and more.

As tempting as it is, don't spend all day kicking back indoors. Get out and see the area's family-friendly attractions, starting with Main Street Berlin.

What are the best large houses to rent with indoor pools in or near Ocean Pines?

Nothing says fancy-schmancy like having a pool right inside your house. Pack your bikini and take a dip in the comfort and privacy of one of these large vacation homes in or near Ocean Pines:

  • Invite friends and family over for a leisurely paddle around at "Updated 3 Bedroom 2 Bathroom Home". This property has space to spare, with 3 bedrooms sleeping up to 8 guests. A swimming pool and a kitchen are other things to love about this place.
  • Another inviting option is "This Is It Rancher Central To Beaches". With 4 bedrooms accommodating up to 10 people, you can invite all your friends to stay with you and swim. A swimming pool and a nearby waterfront are other amenities on offer here.

Want to see our full range of options? Find your dream pad by using the search bar at the top of the page. Simply adjust the filters to find the Ocean Pines vacation rental that's perfect for you.

Are there one-bedroom vacation rentals in or near Ocean Pines?

There sure are. You'll find a good variety of one-bedroom vacation rentals in or near Ocean Pines. If space is not a priority, one of these properties is sure to be a perfect fit:

  • Take a peek at "Beautiful 3 Bedroom Unit At Resort", a fantastic centrally located one-bedroom property. A fireplace and a sauna are available for use here.
  • Or perhaps "Beautiful 3 Bedroom Unit At Resort" is better suited. Another conveniently located one-bedroom option, this place has a swimming pool, a sauna and more.