Ocean Pines Rentals

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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.

Top Ocean Pines property types

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House rentals

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Condo rentals

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Popular amenities for Ocean Pines vacation rentals

Popular
Dog-friendly Internet Pool
The Point 1437
5 Bedroom | 3.5 Bath | Sleeps 10

The Point 1437 - Ocean Pines, MD

$404 avg / night
(excludes fees and taxes)
4.67 (3)
5 Whitecap
5 Bedroom | 3 Bath | Sleeps 10

5 Whitecap - Ocean Pines, MD

$369 avg / night
(excludes fees and taxes)
Battersea on the Canal
5 Bedroom | 3.5 Bath | Sleeps 10

Battersea on the Canal - Ocean Pines, MD

$359 avg / night
(excludes fees and taxes)
4.23 (26)
Drawbridge Rd 38
4 Bedroom | 2 Bath | Sleeps 8

Drawbridge Rd 38 - Ocean Pines, MD

$319 avg / night
(excludes fees and taxes)
4.0 (12)
Beaconhill Road 68
3 Bedroom | 2.5 Bath | Sleeps 8

Beaconhill Road 68 - Ocean Pines, MD

$181 avg / night
(excludes fees and taxes)

View 17 more homes

Recent Ocean Pines guest reviews

Nice house and location right on canal. Hope to return.
Chris T. | Aug 2026
We stayed at this beautiful home over the weekend with family and friends to celebrate my 60th birthday, and it was the perfect place for such a special occasion. The house was exceptionally clean, well organized, spacious, and very comfortable. All five bedrooms, as well as the living room, kitchen, dining area, and sunroom, were thoughtfully decorated with an ocean-inspired theme that immediately put us in a relaxing vacation mood. There was truly something for everyone. The kids enjoyed the playground and swings, and the deck was a wonderful place to enjoy breakfast and morning coffee, and the sunroom offered a peaceful space to sit, relax, and reflect. The location was another big advantage. It is only about 15–20 minutes from Ocean City, close enough to easily enjoy the beach and attractions while being far enough away to escape the crowds and enjoy a quiet, peaceful setting. For a large family or group of friends, this is an excellent choice. The house comfortably accommodates up to 10 people and gave us plenty of space to enjoy time together without feeling crowded. We made wonderful memories here celebrating my 60th birthday, and I would absolutely recommend this home. We would be very happy to stay here again!
Dereje T. | Aug 2026
Overall, the house itself was nice. It was spacious, located in a beautiful wooded area, and had everything we needed for our stay. It was also pretty clean, although the floors could definitely use a good deep scrub. Because the home is in the woods, there were quite a few mosquitoes both inside and outside, although that may have been due to a previous guest leaving the doors open. Unfortunately, our experience with the property management was extremely disappointing, and that is what ultimately ruined our vacation. The first major issue was that our front door would not lock. We immediately reported it and were told someone would come out, but no one showed up that night. We had to sleep in an unfamiliar area with an unlocked front door. We ended up putting a chair underneath the door handle and having someone sleep in the living room so we could feel somewhat safe. This was especially frustrating because we had children with us. We also had one of the shower handles break during our stay. To be fair, that issue was addressed within a few hours, and we appreciated the quick response. However, compared to everything else we were dealing with, that was obviously the least of our worries. The most serious issue was the fire alarm system. It began going off at 5:45 AM and continued until at least 8 PM, when we ultimately left, so it could have continued even longer. It was a whole-house alarm and was so loud that it was impossible to be in the house. Our neighbors could even hear it and came over to check on us as well as the fire department. Despite repeatedly reporting it, no one from property management ever came out to address the alarm. We believed one of the locked rooms may have been triggering the system, but no one from management ever came to properly resolve the issue. We were repeatedly told someone would contact us regarding the various issues, but the communication and follow-through were extremely poor. We lost multiple days of our vacation waiting around for maintenance people who either came very late, were unable to resolve the issue, or simply never showed up. We still have not been contacted regarding the situation. Because we could not get anyone to address the problem, we ultimately had no choice but to pack up our children and leave in the middle of the night to drive home, losing yet another vacation day. What makes this especially disappointing is that we booked this trip months in advance and were incredibly excited about it. Instead, we spent a significant portion of our vacation dealing with house issues, waiting for maintenance, and trying to get someone to take our concerns seriously. To be clear, my complaints are not about the house itself. The house was nice and had a lot of potential for a great vacation!
Paris P. | Aug 2026
Ocean Pines vacation rental FAQ

Yes. 2098 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 the 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 problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Ocean Pines, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
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Seamless check-in
Vacasa Guest Value Prop Icons 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!