Ocean Pines Rentals

Compare 45 vacation rentals.
USA > Maryland > Ocean Pines

Make Ocean Pines your next getaway

There's a lot more to Maryland than fantastic seafood and being the birthplace of Babe Ruth, Tom Clancy, and Edgar Allen Poe! Learn more about this eclectic state right in Ocean Pines, the perfect coastal getaway for your next vacation. With quick access to fishing, boating, nature trails, and shopping, there's something for everyone staying in one of our vacation rentals in this peaceful community.

Explore Ocean Pines house rentals, townhouses, and more


House rentals

View 41 House rentals


View 4 Townhouses

Ocean Pines vacation rentals for every getaway

Dog-friendly Hot tub Internet
Newport Dr 82
6 Bed | 3.5 Bath | Sleeps 12

Newport Dr 82 - Ocean Pines, MD

$500 avg / night
Teal Haven
3 Bed | 2 Bath | Sleeps 10

Teal Haven - Ocean Pines, MD

$219 avg / night
5 Whitecap
5 Bed | 3 Bath | Sleeps 10

5 Whitecap - Ocean Pines, MD

$470 avg / night
Turtle Shores-22 Boston
3 Bed | 2.5 Bath | Sleeps 12 (10 Adults Max)

Turtle Shores-22 Boston - Ocean Pines, MD

$297 avg / night
Whimsy Waterfront
3 Bed | 2 Bath | Sleeps 6

Whimsy Waterfront - Ocean Pines, MD

$261 avg / night

View 40 more homes

Recent Ocean Pines vacation rental reviews

The house was exactly as advertised. It was very clean and had all that we needed for a comfortable stay. Nothing was amiss. If you are looking for a quiet getaway in Ocean Pines, I would recommend this house.
John H. | Jan 2024
Stayed here before and always been a positive experience. Clean, easy to work with, and good location between OCMD and Berlin.
Eric S. | Jan 2024
This home was amazing to spend our Christmas away from home!
Rachel B. | Jan 2024
Ocean Pines Frequently Asked Questions

Yes, 169 of our Ocean Pines homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 2415 of our Ocean Pines vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >

Some of the most popular amenities in our Ocean Pines vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Ocean Pines team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Ocean Pines, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

Where is Ocean Pines?

Nestled among the pine trees inside the city limits of historic Berlin, Maryland, on 3,500 acres of former farmland and woodland, Ocean Pines is an ideal home base for exploring the nearby waterways and beaches. Isle of Wight Bay separates Ocean Pines from the significantly more bustling Ocean City, located just eight miles east. Known for its beaches, theme park attractions, and resort feel, it's easy to take a quick drive to this neighboring city from your vacation rental in Ocean Pines.

Things to do in Ocean Pines

Guests of our Ocean Pines vacation homes looking for a little outdoor excitement will not be disappointed! This serene community offers two marinas, a championship golf course, tennis complex, basketball courts, lakes, parks, playgrounds, and nature trails.

If you're up for a little angling, take a boat out on the waters surrounding the Isle of Wight wildlife conservation area known for croaker, sea trout, flounder, and bluefish, only six miles from your vacation rental.

For a little more activity, take a short, eight-mile trip over to Ocean City, Maryland's most famous resort, for sun, sand, and a historic and award-winning boardwalk where you can experience plenty of shopping, dining, and entertainment options for the whole family, including Trimper's Rides and Amusements at the southern end of the boardwalk. Join the kids for family bumper cars, tiptoe through the haunted house, ride the Ferris wheel all the way up, or gather your courage and dare to take a ride on the looping roller coaster!

If you're feeling lucky, head five miles south to Berlin and pay a visit to the Casino at Ocean Downs, where you'll find horse racing and over 800 slot machines and electronic table games to keep you occupied. 

Day trips from Ocean Pines

While you're certain to find plenty of exciting things to do right in Ocean Pines, be sure to check out some of the other nearby attractions to make your stay a truly memorable one. There are a number of quaint and historic towns close by, including Pocomoke (40 miles south), Salisbury (30 miles west), and Snow Hill (23 miles southwest). Walk among early American homes, schools, and storefronts, and get a taste of yesteryear in towns that can trace their humble beginnings as far back as the eighteenth and even seventeenth centuries!

Head up north and enjoy tax-free shopping in Delaware outlet malls. From Tommy Hilfiger to Coach, shopping enthusiasts are sure to find something that catches their eye! Spend a day hitting the wide, sandy beaches of Dewey Beach, just 30 miles north, and maybe even time your trip out to watch the King return for Elvis Fest!

If you're looking for some fun on the beach, out on the water, or in historic, early American towns, you'll find it all right here in beautiful Ocean Pines. Book the perfect vacation rental today and see how you can get the most out of your East Coast getaway!