Ocean Pines holiday homes

We found 7,387 holiday rentals — enter your dates for availability
Discover a selection of 122 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:4 Dec - 11 Dec

Private kitchen
Pool
Fitness facility
Exterior
Exceptional
(47 reviews)

Bayside Resort Golf Club Townhome-Walk to pool, playground, tennis. Sleeps 11

Selbyville

8% off
NZ$4,786
for 7 nights, 1 home
NZ$684 per night
includes taxes & fees
Bayside Resort Golf Club Townhome-Walk to pool, playground, tennis. Sleeps 11
Upstairs kitchen/dinete
Terrace/patio
Upstairs sunroom
Upstairs sunroom
Exceptional
(73 reviews)

FAIRWAY TO HEAVEN: GOLF course views and BEACH parking pass

Berlin

5% off
NZ$2,651
for 7 nights, 1 apartment
NZ$379 per night
includes taxes & fees
FAIRWAY TO HEAVEN: GOLF course views and BEACH parking pass
Marina
Living area
Living area
Living area
Exceptional
(10 reviews)

Ocean Pines Chalet

Berlin

5% off
NZ$3,407
for 7 nights, 1 home
NZ$487 per night
includes taxes & fees
Ocean Pines Chalet
View of kitchen and dining area.
Exterior
Terrace/patio
Loft
Exceptional
(18 reviews)

Summer Breeze - Waterfront Cottage For Rent

Berlin

8% off
NZ$5,060
for 7 nights, 1 home
NZ$723 per night
includes taxes & fees
Summer Breeze - Waterfront Cottage For Rent
Interior
Room
Living area
Exterior detail
Exceptional
(44 reviews)

Ocean Pines Retreat with Beach Club

Berlin

8% off
NZ$3,330
for 7 nights, 1 home
NZ$476 per night
includes taxes & fees
Ocean Pines Retreat with Beach Club
Exterior
Private kitchen
Living area
Dining
Exceptional
(30 reviews)

Newley Renovated Beach Home, Min. to Ocean City,1st FL. Master Suite, walk in

Berlin

7% off
NZ$3,559
for 7 nights, 1 home
NZ$508 per night
includes taxes & fees
Newley Renovated Beach Home, Min. to Ocean City,1st FL. Master Suite, walk in
Interior
Pool
Exterior
Room
Exceptional
(5 reviews)

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

Berlin

8% off
NZ$4,624
for 7 nights, 1 home
NZ$661 per night
includes taxes & fees
Cozy house in Ocean pines, only 10 mins away from Ocean City.
Sunroom
Sunroom
Kitchen / Living Room
Kitchen
Exceptional
(127 reviews)

Pet Friendly Near Berlin, Assateague Island Beaches and Ocean City

Berlin

7% off
NZ$2,223
for 7 nights, 1 home
NZ$318 per night
includes taxes & fees
Pet Friendly Near Berlin, Assateague Island Beaches and Ocean City
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
Kitchen remodel completed Fall 2024
Exceptional
(29 reviews)

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

Berlin

7% off
NZ$2,927
for 7 nights, 1 home
NZ$418 per night
includes taxes & fees
Private and pet-friendly, with game room and upgraded kitchen
Interior
Pool
Exterior
Living area
Exceptional
(61 reviews)

Bear Trap Dunes: Spacious and Sparkling 3 Bedroom with All the Amenities!

Ocean View

8% off
NZ$2,666
for 7 nights, 1 home
NZ$381 per night
includes taxes & fees
Bear Trap Dunes: Spacious and Sparkling 3 Bedroom with All the Amenities!
Private kitchen
Interior
Sit by the water with a coffee or cocktail!
Dock for crabbing or watching wildlife
Exceptional
(101 reviews)

Stay at Heron Cove located in popular Mallard Lakes!

Selbyville

9% off
NZ$1,118
for 7 nights, 1 apartment
NZ$160 per night
includes taxes & fees
Stay at Heron Cove located in popular Mallard Lakes!
Screened-in deck
Back deck off of bedroom and screened-in deck off of living room.
View of playground from back deck
Kitchen
Exceptional
(204 reviews)

Gorgeous Renovated Townhouse-MUST BE OVER 25 TO RENT

Ocean City

8% off
NZ$2,667
for 7 nights, 1 home
NZ$381 per night
includes taxes & fees
Gorgeous Renovated Townhouse-MUST BE OVER 25 TO RENT
Living area
Property grounds
Exterior
Private kitchen
Exceptional
(111 reviews)

Direct Oceanfront 3 bedroom condo perfect for family and friends with pools

Ocean City

7% off
NZ$2,680
for 7 nights, 1 apartment
NZ$383 per night
includes taxes & fees
Direct Oceanfront 3 bedroom condo perfect for family and friends with pools
Living area
Interior
Living area
Dining
Exceptional
(53 reviews)

10 minute walk to the beach! Family- size condo

Ocean City

8% off
NZ$2,547
for 7 nights, 1 apartment
NZ$364 per night
includes taxes & fees
10 minute walk to the beach! Family- size condo
ADAGIO UNIT 207
LIVING ROOM
MASTER BEDROOM
LIVING ROOM
Exceptional
(94 reviews)

ADAGIO#207 BEAUTIFUL 3 BED/3 BATH OCEAN BLOCK CONDO W/INDOOR POOL STEPS TO BEACH

Ocean City

7% off
NZ$4,017
for 7 nights, 1 apartment
NZ$574 per night
includes taxes & fees
ADAGIO#207 BEAUTIFUL 3 BED/3 BATH OCEAN BLOCK CONDO W/INDOOR POOL STEPS TO BEACH
Private kitchen
Great sunset views of the bay!
Property grounds
Nice fireplace with 50” flatscreen tv above
Exceptional
(147 reviews)

BEAUTIFUL & CLEAN! Waterfront condo with epic sunsets and a POOL!

Ocean City

7% off
NZ$2,438
for 7 nights, 1 apartment
NZ$348 per night
includes taxes & fees
BEAUTIFUL & CLEAN! Waterfront condo with epic sunsets and a POOL!
Exterior
Super clean , fun condo to stay in
Ocean Front balcony, great place to relax and watch the waves!
Watch the waves, play games, watch tv! All the comforts of home !
Exceptional
(111 reviews)

Delightful Escape, Oceanfront 2BDR , Awesome Views, Pool, Clean!

Ocean City

7% off
NZ$2,620
for 7 nights, 1 apartment
NZ$374 per night
includes taxes & fees
Delightful Escape, Oceanfront 2BDR , Awesome Views, Pool, Clean!
Living area
Exterior
Room
Interior
Exceptional
(9 reviews)

Broad Marsh Beach Home | Pool + Balcony Views

Ocean City

5% off
NZ$4,093
for 7 nights, 1 apartment
NZ$585 per night
includes taxes & fees
Broad Marsh Beach Home | Pool + Balcony Views
Terrace/patio
Exterior
Bathroom
Bathroom
Exceptional
(90 reviews)

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

Ocean City

8% off
NZ$4,357
for 7 nights, 1 apartment
NZ$622 per night
includes taxes & fees
Great Location for your vacation. Very Pet Friendly!. Close to Boardwalk/Beach.
Interior
view from balcony to living area
Ocean Front view of the Pyramid the most unique building on the beach
Relax, Have dinner, Play games, see the ocean!
Exceptional
(101 reviews)

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

Ocean City

7% off
NZ$2,620
for 7 nights, 1 apartment
NZ$374 per night
includes taxes & fees
Escape to The Ocean! , Ocean Front, Beautiful View, Pool!
Indoor Pool (Open Summer months Only)
Winter is a Great Time to Enjoy the Beach!
Bedroom with Two Full-Size Beds & Flat-Screen HDTV
Lit Entry Hall to Condo - Front Door on Right.
Exceptional
(30 reviews)

Direct Ocean Front...In The Middle of it All!!!

Ocean City

6% off
NZ$7,039
for 7 nights, 1 apartment
NZ$1,006 per night
includes taxes & fees
Direct Ocean Front...In The Middle of it All!!!
Interior
Interior
Private kitchen
Exceptional
(65 reviews)

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

Ocean City

8% off
NZ$3,263
for 7 nights, 1 apartment
NZ$466 per night
includes taxes & fees
Beachfront living near Seacrets! Don't let this memorable getaway pass you by.
Dining
Living area
Dining
Dining
Exceptional
(53 reviews)

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

Ocean City

7% off
NZ$2,561
for 7 nights, 1 apartment
NZ$366 per night
includes taxes & fees
No need to look any further for a one bedroom in OC. Long term rates available.
Pool
Property grounds
Beach
Interior
Exceptional
(55 reviews)

Direct Oceanfront Condo remodeled with Breathtaking Views from two private decks

Ocean City

8% off
NZ$3,562
for 7 nights, 1 apartment
NZ$509 per night
includes taxes & fees
Direct Oceanfront Condo remodeled with Breathtaking Views from two private decks
  • 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

What is the most popular type of holiday home accommodation in Ocean Pines?
Based on our research, houses are the most desirable type of holiday home in Ocean Pines. But of course, everyone's idea of the perfect stay differs. Bookabach has holiday homes of all sizes and shapes, and we'll help you to find the perfect match.
How much does it cost to rent a holiday home in Ocean Pines?
Property type, length of stay and season are some of the conditions that can influence the price of a holiday home. Simply click on your travel dates to find your perfect fit. From comfy cottages to expansive luxury villas, all Bookabach holiday homes provide unbeatable value.
How much does it cost to rent a beach house in Ocean Pines?
Prices for beach houses in Ocean Pines vary depending on the style and size of the property and time of year you're travelling. Simply enter your dates of travel into Bookabach and the number of guests to view holiday home options and prices. From there you can use our filters to refine your search results by nearby activities, ratings, amenities and more.
Are there pet-friendly holiday homes in Ocean Pines?
Pack up a suitcase for the pooch in your life because Ocean Pines has 173 stays that welcome pets with open arms. Let your four-legged pal join in on the family trip at one of our pet-friendly holiday homes on Bookabach. Simply enter your travel dates then check the "Pets allowed" filter box.
Can I rent a house with a pool in Ocean Pines?
Grab your swimsuit and pool noodle, because there are 128 houses with a private pool in Ocean Pines. Stay at one of these superb holiday homes and you'll enjoy pool days every day. Simply enter your dates into Bookabach, then check the "pool" filter to find a place to make a splash!
What are popular home amenities in Ocean Pines?
A nearby waterfront, a lake view and a swimming pool are the most popular home amenities in Ocean Pines. Whether you're taking a trip by yourself, with your other half or a bunch of friends, Bookabach can help you find a holiday home that suits your style with all the features you'll enjoy.
Are there large group holiday homes in Ocean Pines?
You can choose from 44 holiday homes in Ocean Pines that can host a group of 10 or more people. Whether you're organising a holiday with extended family or a celebration like an anniversary, there's ample space to get your favourite people together under the same roof.
Are there holiday homes in Ocean Pines that welcome kids?
With 173 family-friendly holiday homes to choose from in Ocean Pines, now is the perfect time to introduce your little ones to the pleasures of travel. Simply click on our "Properties good for families" filter to look for stays that feature conveniences perfect for families on the move, such as multiple bedrooms, pools, hot tubs and bunk beds.
What are the top attractions for families in Ocean Pines?
Keeping the kids entertained during your stay in Ocean Pines is simple with these top family-friendly attractions:
  • Frontier Town Water Park and Golf
  • GlenRiddle Golf Club
  • River Run Golf Club
Are there one-bedroom holiday homes in Ocean Pines?
Yes, there are two one-bedroom properties in Ocean Pines to pick from. A one-bedroom holiday home is a great option if it's only two of you or if you're holidaying alone. Add in more convenience, space and privacy compared to a hotel, and you've got the makings of an unforgettable trip.
Can I find two-bedroom holiday homes in Ocean Pines?
Choose from 14 two-bedroom homes in Ocean Pines. Settle the kids into the second room or fill it with a couple of your nearest and dearest friends. There's a spot for whoever's lucky enough to be joining your journey.
Are there holiday homes with WiFi in Ocean Pines?
Whether you want to keep up with the headlines, make a video call or update your social media accounts, there are 41 holiday homes with WiFi in Ocean Pines. Check the "WiFi" box when searching on Bookabach and stay connected on your getaway.
How can I find holiday homes with air conditioning in Ocean Pines?
Ocean Pines has 166 holiday homes where you'll be able to spend your days in air-conditioned comfort. To find a stay on Bookabach that features this amenity, enter your desired travel dates and use the convenient filters to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Ocean Pines?
The minimum age requirements can differ across properties on Bookabach, so be sure to check the rules of the holiday home in Ocean Pines you want to book. But typically, it's 16, 18 or 21.
How long can I rent a holiday home in Ocean Pines for?
The amount of time you can rent an Ocean Pines holiday home for is down to each property. Just put in your dates of travel to see available options offering longer term stays. They come with all the things you need to make your extended break more enjoyable and convenient, such as kitchens and air conditioning. Some holiday homes may also offer weekly or monthly discounts, so you can stick around for longer for less.

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