Ocean Pines Rentals

Compare 51 vacation rentals. Enter your trip dates to get started.
USA > Maryland > Ocean Pines

Make Ocean Pines your next getaway—choose from 51 great vacation rentals

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, duplexes, and more


House rentals

View 41 House rentals


View 6 Townhouses


View 2 Duplexes

Ocean Pines vacation rentals for every getaway

Dog-friendly Hot tub Internet
Evergreen Shadow 3D Tour
3 Bedroom | 2 Bath | Sleeps 8

Evergreen Shadow - Ocean Pines, MD

From $89
Sailors Delight on Ocean Pkwy 3D Tour
4 Bedroom | 2 Bath | Sleeps 10

Sailors Delight on Ocean Pkwy - Ocean Pines, MD

From $114
Ocean Pines 74 - High Sheriff 3D Tour
3 Bedroom | 2.5 Bath | Sleeps 7

Ocean Pines 74 - High Sheriff - Ocean Pines, MD

From $89
Whimsical Willow 3D Tour
3 Bedroom | 2 Bath | Sleeps 8

Whimsical Willow - Ocean Pines, MD

From $104
Ambleside Court 9 3D Tour
3 Bedroom | 2 Bath | Sleeps 8

Ambleside Court 9 - Ocean Pines, MD

From $89

View 46 more homes

Recent Ocean Pines vacation rental reviews

We loved our stay at the bright, cheery round house. The house accommodated the 8 of us with everything needed. Loads of towels, blankets, fluffy pillows, spices in the kitchen and shampoo and conditioners in the bathroom. Although the weather was rainy the whole time the close proximity to Ocean City and local restaurants helped make our stay special.
Robert G. | May 2022
Place was cleaned nicely and good location. However I had to contact them for the check in code, which they never sent me. And the grill was missing, this was annoying because all of the food we brought was hamburgers and hotdogs, sausage etc... the grill is still listed in the description and pictures. That’s something they should have told me, especially when they’re advertising more of an outdoor experience home.
Emily L. | May 2022
Love that my dog was able to come with.
deborah M. | May 2022

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!