Ocean Pines holiday homes

We found 7,255 holiday rentals — enter your dates for availability
Discover a selection of 117 homes and other holiday rentals in Ocean Pines that are perfect for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll have the best amenities for spending time at your home away from home, which might include parking and a garden. At the end of the day, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Ocean Pines

Showing deals for:15 Jan - 22 Jan

Upstairs kitchen/dinete
Terrace/patio
Upstairs sunroom
Upstairs living room
Exceptional
(73 reviews)

FAIRWAY TO HEAVEN: GOLF course views and BEACH parking pass

Berlin

5% off
NZ$2,793
for 7 nights, 1 apartment
NZ$399 per night
includes taxes & fees
FAIRWAY TO HEAVEN: GOLF course views and BEACH parking pass
Living area
Living area
Living area
Living area
Exceptional
(11 reviews)

Ocean Pines Chalet

Berlin

5% off
NZ$4,495
for 7 nights, 1 home
NZ$642 per night
includes taxes & fees
Ocean Pines Chalet
Exterior
Property grounds
Living area
Room
Exceptional
(108 reviews)

Huge Direct Oceanfront Townhouse with Beautiful Sunrises

Ocean City

7% off
NZ$4,266
for 7 nights, 1 home
NZ$609 per night
includes taxes & fees
Huge Direct Oceanfront Townhouse with Beautiful Sunrises
View of kitchen and dining area.
Exterior
Front Entrance
Loft
Exceptional
(18 reviews)

Summer Breeze - Waterfront Cottage For Rent

Berlin

8% off
NZ$5,304
for 7 nights, 1 home
NZ$758 per night
includes taxes & fees
Summer Breeze - Waterfront Cottage For Rent
Living area
Exterior
Private kitchen
Dining
Exceptional
(93 reviews)

Great Location for your vacation. Very Pet Friendly!. Close to Boardwalk/Beach.

Ocean City

8% off
NZ$4,378
for 7 nights, 1 apartment
NZ$625 per night
includes taxes & fees
Great Location for your vacation. Very Pet Friendly!. Close to Boardwalk/Beach.
Room
Pool
Interior
Property grounds
Exceptional
(5 reviews)

Cozy house in Ocean pines, only 10 mins away from Ocean City.

Berlin

8% off
NZ$4,845
for 7 nights, 1 home
NZ$692 per night
includes taxes & fees
Cozy house in Ocean pines, only 10 mins away from Ocean City.
Room
View from the Kitchen and living room. Back Deck
Living area
Private kitchen
Exceptional
(31 reviews)

SERENE WATER VIEWS-Relaxing family beach house

Ocean City

8% off
NZ$6,593
for 7 nights, 1 home
NZ$942 per night
includes taxes & fees
SERENE WATER VIEWS-Relaxing family beach house
Interior
Interior
Private kitchen
Property grounds
Exceptional
(67 reviews)

Beachfront living near Seacrets! Don't let this memorable getaway pass you by.

Ocean City

8% off
NZ$3,435
for 7 nights, 1 apartment
NZ$491 per night
includes taxes & fees
Beachfront living near Seacrets! Don't let this memorable getaway pass you by.
Interior
Room
Exterior detail
Terrace/patio
Exceptional
(46 reviews)

Ocean Pines Retreat with Beach Club

Berlin

8% off
NZ$3,575
for 7 nights, 1 home
NZ$511 per night
includes taxes & fees
Ocean Pines Retreat with Beach Club
Fully equipped kitchen
Community pool - short walk
Dining area
Great room
Exceptional
(28 reviews)

Available for Rent 2025! Bear Trap Condo - overlooking hole #2

Ocean View

7% off
NZ$3,512
for 7 nights, 1 apartment
NZ$502 per night
includes taxes & fees
Available for Rent 2025! Bear Trap Condo - overlooking hole #2
Dining room for 8; doors can close for privacy in sitting room
Larger couch and ottoman, open to kitchen
There are 5 community pools available to guests for a daily fee
Old fireplace was replaced with electric fireplace w/ remote control
Exceptional
(31 reviews)

Private and pet-friendly, with game room and upgraded kitchen

Berlin

7% off
NZ$3,083
for 7 nights, 1 home
NZ$440 per night
includes taxes & fees
Private and pet-friendly, with game room and upgraded kitchen
Exterior
Dining
Private kitchen
Dining
Exceptional
(16 reviews)

LAST DATES! Bay Sunset Getaway • Pool • 2BR/2BA • Free Linens

Ocean City

8% off
NZ$6,393
for 7 nights, 1 apartment
NZ$913 per night
includes taxes & fees
LAST DATES! Bay Sunset Getaway • Pool • 2BR/2BA • Free Linens
ext+deck+vfne
Living area
05-1Q7A4356
06-1Q7A4263
Wonderful
(9 reviews)

Biscayne Bungalow– Coastal Charm Near the Beach

Ocean City

5% off
NZ$3,975
for 7 nights, 1 home
NZ$568 per night
includes taxes & fees
Biscayne Bungalow– Coastal Charm Near the Beach
Living area
Living area
Beach
Pool
Exceptional
(58 reviews)

Beautiful Beachfront 2 Level Penthouse w 2 balconies! Full Ocean Views SLEEPS 7!

Ocean City

7% off
NZ$9,836
for 7 nights, 1 apartment
NZ$1,405 per night
includes taxes & fees
Beautiful Beachfront 2 Level Penthouse w 2 balconies! Full Ocean Views SLEEPS 7!
Ocean Front view of the Pyramid the most unique building on the beach
view from balcony to living area
Breathtaking nighttime view from the condo
Interior
Exceptional
(103 reviews)

Escape to The Ocean! , Ocean Front, Beautiful View, Pool!

Ocean City

7% off
NZ$2,415
for 7 nights, 1 apartment
NZ$345 per night
includes taxes & fees
Escape to The Ocean! , Ocean Front, Beautiful View, Pool!
Diamond Head - less than a half block to the beach and close to many OC attractions
Kitchen with all major appliances and 2-seat breakfast bar
Beautiful ocean views
Beautiful ocean views
Exceptional
(15 reviews)

Private Pool Steps From the Beach

Ocean City

7% off
NZ$2,223
for 7 nights, 1 apartment
NZ$318 per night
includes taxes & fees
Private Pool Steps From the Beach
Private kitchen
Living area
Living area
Interior
Exceptional
(12 reviews)

Brand New 3-bedroom, 3 1/2 bathroom townhome walking distance to the beach.

Ocean City

12% off
NZ$12,166
for 7 nights, 1 home
NZ$1,738 per night
includes taxes & fees
Brand New 3-bedroom, 3 1/2 bathroom townhome walking distance to the beach.
Private kitchen
Pool
Interior
Sports court
Exceptional
(6 reviews)

2BR Condo,Pools & Walk to Beach

Ocean City

7% off
NZ$3,429
for 7 nights, 1 apartment
NZ$490 per night
includes taxes & fees
2BR Condo,Pools & Walk to Beach
Living area
Living area
Interior
Property grounds
Exceptional
(72 reviews)

12th St & Boardwalk, Direct Oceanfront Amazing View

Ocean City

7% off
NZ$1,798
for 7 nights, 1 apartment
NZ$257 per night
includes taxes & fees
12th St & Boardwalk, Direct Oceanfront Amazing View
Private kitchen
Exterior
Room
Interior
Exceptional
(87 reviews)

Great Location for your vacation. Very Pet Friendly!. Close to Boardwalk/Beach.

Ocean City

8% off
NZ$4,378
for 7 nights, 1 apartment
NZ$625 per night
includes taxes & fees
Great Location for your vacation. Very Pet Friendly!. Close to Boardwalk/Beach.
Dining
Room
Exterior
Room
Exceptional
(47 reviews)

V73 - Beautiful 3BR/2BA Ocean View! Pet-Friendly! Just one bldg from the beach!

Ocean City

7% off
NZ$3,106
for 7 nights, 1 apartment
NZ$444 per night
includes taxes & fees
V73 - Beautiful 3BR/2BA Ocean View! Pet-Friendly! Just one bldg from the beach!
Dock for crabbing or watching wildlife
Interior
Interior
Private kitchen
Exceptional
(105 reviews)

Stay at Heron Cove located in popular Mallard Lakes!

Selbyville

9% off
NZ$1,290
for 7 nights, 1 apartment
NZ$184 per night
includes taxes & fees
Stay at Heron Cove located in popular Mallard Lakes!
Dining
Living area
Dining
Dining
Exceptional
(59 reviews)

No need to look any further for a one bedroom in OC. Long term rates available.

Ocean City

7% off
NZ$2,695
for 7 nights, 1 apartment
NZ$385 per night
includes taxes & fees
No need to look any further for a one bedroom in OC. Long term rates available.
Interior
Living area
Room
Private kitchen
Exceptional
(9 reviews)

Makai Sunset Cove all-season indoor pool

Ocean City

5% off
NZ$2,536
for 7 nights, 1 apartment
NZ$362 per night
includes taxes & fees
Makai Sunset Cove all-season indoor pool
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Ocean Pines

  • Scenic Beaches: Enjoy the beautiful sandy beaches perfect for sunbathing and swimming, offering a relaxing coastal experience.
  • Outdoor Activities: Engage in various recreational activities, from leisurely walks along the esplanade to fun family outings at local parks.
  • Cultural Experiences: Immerse yourself in the rich local culture through community events and charming neighbourhood interactions.
  • Serene Ocean Views: Take in breathtaking ocean vistas that provide a picturesque backdrop for a romantic getaway or family adventure.
  • Amusement Attractions: Visit engaging amusement parks that offer exciting rides and entertainment for visitors of all ages.

Top attractions near Ocean Pines

Ocean Pines offers a delightful mix of outdoor and beach experiences perfect for a romantic or family getaway. Enjoy the sandy beach, scenic esplanade, and engaging amusement park, all designed to provide a rich cultural and beach holiday experience. Whether you're looking for a leisurely stroll or fun family activities, Ocean Pines in Berlin, Maryland delivers a memorable blend of natural beauty and local charm.

  • Ocean City Beach: A stunning stretch of sandy shoreline perfect for sunbathing and swimming, this beach offers a vibrant atmosphere with various water activities and beachfront dining.
  • Jolly Roger Amusement Park: This amusement park is a hub of outdoor fun, featuring thrilling rides and family-friendly attractions, ideal for a day full of adventure and excitement.
  • Ripley's Believe It or Not. A fascinating museum showcasing oddities and curiosities from around the world, providing a unique glimpse into the bizarre and extraordinary.

Things to do recommended for couples

For a romantic getaway in Ocean Pines, consider a sunset kayak tour on the tranquil waters or a leisurely stroll along the picturesque beaches of Assateague Island. Indulge in a candlelit dinner at a charming local restaurant, and don't miss the chance to explore the scenic coastal trails together.

Things to do recommended for families

Families visiting Ocean Pines can enjoy a day at local parks, explore interactive exhibits at community museums, and take part in kid-friendly activities at the waterfront. Experience the charm of Maryland with plenty of local delights for all ages.

Things to do recommended for groups

Explore Ocean Pines with your mates, enjoying local hikes, fishing, and scenic cycling routes. Discover the charm of Maryland’s coastal lifestyle and sample fresh seafood at local eateries for an authentic group adventure.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Ocean Pines

Whether you're journeying with a group, as a family, with your furry mates, or planning an extended stay, make sure to refine your search with the appropriate priorities. Below are some Vrbo booking pointers for you.

  • Traveling to Ocean Pines with a group: Consider how many bedrooms will suit your needs, along with extra features like a full kitchen or a backyard for group outings. Luckily, you can easily filter for all these options—and more—on Vrbo.
  • Traveling to Ocean Pines with young kids: Traveling with little ones can be demanding. You'll want to ensure their comfort and safety while providing age-suitable amenities, such as a private swimming pool. It's also wise to consider how close you are to family-friendly attractions.
  • Taking your pets with you to Ocean Pines: For many families, a trip just isn’t the same without their furry companion by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Ocean Pines: If you're in search of holiday rentals with great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include preferences like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Ocean Pines

Ocean Pines in Berlin, Maryland offers a charming coastal escape ideal for a romantic or family-friendly getaway. Explore scenic beaches, relaxed outdoor activities, and a historical atmosphere in this friendly neighbourhood. Enjoy leisurely strolls, local recreation, and the serene ocean view, making it a perfect destination for travellers seeking a mix of relaxation and cultural experiences.

  • Ocean City: Situated a mere 10km from Ocean Pines, Ocean City is a vibrant coastal city renowned for its outdoor, romantic, and family-friendly experiences. Visitors can enjoy the iconic boardwalk that stretches for miles, lined with shops, eateries, and entertainment options. The local water park adds a splash of fun for families, while the pristine beaches offer a perfect spot for relaxation and sunbathing. Notable landmarks include the esplanade and family beach, making Ocean City a must-visit destination for those seeking a lively beach atmosphere.
  • Isle of Wight: Located just 5km from Ocean Pines, Isle of Wight is a picturesque island that beckons outdoor enthusiasts and families alike. With its charming boardwalk and a local theatre providing cultural experiences, the island is perfect for a leisurely day out. Golf courses offer recreation for sports lovers, while the stunning bay and marina create opportunities for water activities like boating and fishing. The natural beauty and tranquil ambiance of Isle of Wight make it an ideal spot for romantic getaways and family adventures.
  • North Ocean City: Also situated 10km from Ocean Pines, North Ocean City is a delightful neighbourhood known for its outdoor, romantic, and beach experiences. The area boasts a lively boardwalk and shopping area, making it a great place for leisurely strolls and shopping excursions. Families can enjoy the local recreation park, while the nearby beaches provide ample space for sunbathing and beach games. With its inviting atmosphere, North Ocean City is perfect for those looking to unwind and immerse themselves in beach life.

Best time to go to Ocean Pines

If you're planning a trip to Ocean Pines, it's a good idea to check both the weather and property rates. The warmest month is July.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January38.1°F (3.4°C)Light RainMostly SunnyAverage
February40.1°F (4.5°C)Light RainMostly SunnyAverage
March45.3°F (7.4°C)Light RainMostly SunnyAverage
April54.5°F (12.5°C)Light RainMostly SunnyAverage
May63.1°F (17.3°C)Light RainMostly SunnyAverage
June72.0°F (22.2°C)Light RainMostly SunnyHigh
July77.5°F (25.3°C)Light RainMostly SunnyHigh
August76.3°F (24.6°C)Light RainMostly SunnyHigh
September71.2°F (21.8°C)Light RainMostly SunnyAverage
October62.1°F (16.7°C)Light RainMostly SunnyLow
November50.9°F (10.5°C)Light RainMostly SunnyLow
December44.1°F (6.7°C)Light RainMostly SunnyLow

Booking with Vrbo is a breeze

Are you hoping to save on your next adventure? Being flexible with your travel dates can really pay off, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To help you discover the perfect Vrbo property that fits your budget, utilise our filters to sort by price, location, and type of holiday rental. We're here to support you in finding the best options for your trip.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a handy way to plan your trips, revisit your previous arrangements, or keep track of your travel plans. You can easily find the properties you've saved or booked, organised into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

When is the best time to visit Ocean Pines for a holiday rental?
July is the most popular time to visit Ocean Pines, as the summer peak season runs from June to August. During these months, the area buzzes with activity, attracting families and beachgoers eager to soak up the sun along the beautiful Maryland coastline. The warm temperatures, typically ranging from 20 to 30 degrees Celsius, create the ideal setting for outdoor adventures, whether it's enjoying water sports, golfing, or leisurely strolls along the beach.For those who prefer a more tranquil experience, November presents a fantastic opportunity to visit Ocean Pines at a lower cost. This month offers a quieter atmosphere, allowing visitors to appreciate the natural beauty of the area without the crowds. Crisp autumn air makes for pleasant walks, and the stunning fall foliage adds a unique charm to the landscape.Ultimately, the best time to book a holiday rental in Ocean Pines hinges on your preferences: if you thrive on vibrant summer activities and community events, July is your month. However, if you seek a peaceful retreat with beautiful scenery, consider a visit in November.
What are the top attractions in Ocean Pines, Maryland, United States of America?
In Ocean Pines, visitors can enjoy a variety of attractions and activities that highlight the area's natural beauty and recreational opportunities. The Ocean Pines Golf Club offers a picturesque 18-hole course surrounded by lush landscapes, great for golf enthusiasts. Nearby, the community boasts several parks such as the community centre, which features walking trails, playgrounds, and sports facilities, making it an ideal spot for families.For those looking to explore the waterfront, the nearby Assawoman Bay provides opportunities for kayaking, paddleboarding, and fishing, allowing for a relaxing day on the water. Additionally, Ocean Pines is just a short drive from the bustling resort town of Ocean City, where visitors can find famous boardwalk attractions, amusement parks, and beautiful beaches.
Are all fees included in the Ocean Pines holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Ocean Pines holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Ocean Pines with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Ocean Pines holiday homes?
You can find great discounts on holiday homes in Ocean Pines on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Ocean Pines holiday home booking on Bookabach?
To find Ocean Pines holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Ocean Pines?
A long-stay holiday home in Ocean Pines is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Ocean Pines holiday home?
Book your Ocean Pines holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Ocean Pines?
Prices for holiday homes in Ocean Pines vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Ocean Pines to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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