Ocean Pines holiday rentals

We found 7,378 holiday rentals — enter your dates for availability
Discover a selection of 119 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:11 Dec - 18 Dec

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

FAIRWAY TO HEAVEN: GOLF course views and BEACH parking pass

Berlin

5% off
AU$2,224
for 7 nights, 1 apartment
AU$318 per night
includes taxes & fees
FAIRWAY TO HEAVEN: GOLF course views and BEACH parking pass
Living area
Living area
Living area
Marina
Exceptional
(10 reviews)

Ocean Pines Chalet

Berlin

5% off
AU$2,856
for 7 nights, 1 home
AU$408 per night
includes taxes & fees
Ocean Pines Chalet
Exterior detail
Room
Living area
Terrace/patio
Exceptional
(44 reviews)

Ocean Pines Retreat with Beach Club

Berlin

7% off
AU$2,761
for 7 nights, 1 home
AU$394 per night
includes taxes & fees
Ocean Pines Retreat with Beach Club
View of kitchen and dining area.
Exterior
Front Entrance
Loft
Exceptional
(18 reviews)

Summer Breeze - Waterfront Cottage For Rent

Berlin

8% off
AU$4,162
for 7 nights, 1 home
AU$595 per night
includes taxes & fees
Summer Breeze - Waterfront Cottage For Rent
Property grounds
Pool
Room
Interior
Exceptional
(5 reviews)

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

Berlin

8% off
AU$3,800
for 7 nights, 1 home
AU$543 per night
includes taxes & fees
Cozy house in Ocean pines, only 10 mins away from Ocean City.
Room
Private kitchen
Dining
Exterior
Exceptional
(31 reviews)

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

Berlin

7% off
AU$2,912
for 7 nights, 1 home
AU$416 per night
includes taxes & fees
Newley Renovated Beach Home, Min. to Ocean City,1st FL. Master Suite, walk in
There are 5 community pools available to guests for a daily fee
Larger couch and ottoman, open to kitchen
Old fireplace was replaced with electric fireplace w/ remote control
Kitchen remodel completed Fall 2024
Exceptional
(31 reviews)

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

Berlin

7% off
AU$2,453
for 7 nights, 1 home
AU$350 per night
includes taxes & fees
Private and pet-friendly, with game room and upgraded kitchen
Dock for crabbing or watching wildlife
Interior
Interior
Sit by the water with a coffee or cocktail!
Exceptional
(102 reviews)

Stay at Heron Cove located in popular Mallard Lakes!

Selbyville

9% off
AU$906
for 7 nights, 1 apartment
AU$129 per night
includes taxes & fees
Stay at Heron Cove located in popular Mallard Lakes!
Exterior
Pool
Living area
Living area
Exceptional
(61 reviews)

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

Ocean View

8% off
AU$2,238
for 7 nights, 1 home
AU$320 per night
includes taxes & fees
Bear Trap Dunes: Spacious and Sparkling 3 Bedroom with All the Amenities!
Private kitchen
Living area
Beach
Living area
Exceptional
(57 reviews)

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

Ocean City

7% off
AU$7,343
for 7 nights, 1 apartment
AU$1,049 per night
includes taxes & fees
Beautiful Beachfront 2 Level Penthouse w 2 balconies! Full Ocean Views SLEEPS 7!
Living area
Interior
Dining
Living area
Exceptional
(55 reviews)

10 minute walk to the beach! Family- size condo

Ocean City

8% off
AU$2,098
for 7 nights, 1 apartment
AU$300 per night
includes taxes & fees
10 minute walk to the beach! Family- size condo
Dining Room
Property grounds
Living area
Private kitchen
Exceptional
(111 reviews)

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

Ocean City

7% off
AU$2,206
for 7 nights, 1 apartment
AU$315 per night
includes taxes & fees
Direct Oceanfront 3 bedroom condo perfect for family and friends with pools
LIVING ROOM
LIVING ROOM
MASTER BEDROOM
ADAGIO UNIT 207
Exceptional
(95 reviews)

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

Ocean City

8% off
AU$3,237
for 7 nights, 1 apartment
AU$462 per night
includes taxes & fees
ADAGIO#207 BEAUTIFUL 3 BED/3 BATH OCEAN BLOCK CONDO W/INDOOR POOL STEPS TO BEACH
Nice fireplace with 50” flatscreen tv above
Great sunset views of the bay!
Property grounds
Exterior
Exceptional
(149 reviews)

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

Ocean City

7% off
AU$2,007
for 7 nights, 1 apartment
AU$287 per night
includes taxes & fees
BEAUTIFUL & CLEAN! Waterfront condo with epic sunsets and a POOL!
Welcome to Diamond Head 305 - 1 bedroom, 1.5 bathroom oceanview with building pool
Kitchen with all major appliances and 2-seat breakfast bar
Beautiful ocean views
Beautiful ocean views
Exceptional
(14 reviews)

Private Pool Steps From the Beach

Ocean City

7% off
AU$1,707
for 7 nights, 1 apartment
AU$244 per night
includes taxes & fees
Private Pool Steps From the Beach
Interior
view from balcony to living area
Breathtaking nighttime view from the condo
Relax, Have dinner, Play games, see the ocean!
Exceptional
(102 reviews)

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

Ocean City

7% off
AU$2,158
for 7 nights, 1 apartment
AU$308 per night
includes taxes & fees
Escape to The Ocean! , Ocean Front, Beautiful View, Pool!
Property grounds
Interior
Private kitchen
Exceptional
(66 reviews)

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

Ocean City

8% off
AU$2,581
for 7 nights, 1 apartment
AU$369 per night
includes taxes & fees
Beachfront living near Seacrets! Don't let this memorable getaway pass you by.
Sports court
Pool
Room
Interior
Exceptional
(6 reviews)

2BR Condo,Pools & Walk to Beach

Ocean City

8% off
AU$2,952
for 7 nights, 1 apartment
AU$422 per night
includes taxes & fees
2BR Condo,Pools & Walk to Beach
Living area
Living area
Atrium
Kitchen
Exceptional
(105 reviews)

Direct Oceanfront Condo on 11th Floor with Amazing views of Ocean and Bay

Ocean City

7% off
AU$1,723
for 7 nights, 1 apartment
AU$246 per night
includes taxes & fees
Direct Oceanfront Condo on 11th Floor with Amazing views of Ocean and Bay
Exterior
Private kitchen
Room
Dining
Exceptional
(46 reviews)

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

Ocean City

7% off
AU$2,430
for 7 nights, 1 apartment
AU$347 per night
includes taxes & fees
V73 - Beautiful 3BR/2BA Ocean View! Pet-Friendly! Just one bldg from the beach!
Lit Entry Hall to Condo - Front Door on Right.
Winter is a Great Time to Enjoy the Beach!
Private kitchen
Indoor Pool (Open Summer months Only)
Exceptional
(30 reviews)

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

Ocean City

6% off
AU$5,672
for 7 nights, 1 apartment
AU$810 per night
includes taxes & fees
Direct Ocean Front...In The Middle of it All!!!
Dining
Living area
Dining
Dining
Exceptional
(56 reviews)

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

Ocean City

7% off
AU$2,107
for 7 nights, 1 apartment
AU$301 per night
includes taxes & fees
No need to look any further for a one bedroom in OC. Long term rates available.
Property grounds
Interior
Room
Private kitchen
Exceptional
(49 reviews)

Fantastic Bay View with romantic sunsets!

Ocean City

8% off
AU$1,594
for 7 nights, 1 apartment
AU$228 per night
includes taxes & fees
Fantastic Bay View with romantic sunsets!
40-1Q7A8864
32-1Q7A8831
18-1Q7A8770
45-1Q7A8892
Exceptional
(5 reviews)

Sunkissed Ocean Haven

Ocean City

6% off
AU$3,884
for 7 nights, 1 apartment
AU$555 per night
includes taxes & fees
Sunkissed Ocean Haven
  • 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 coastal paths: Enjoy leisurely walks along the charming beach esplanade with magnificent ocean views.
  • Family-friendly attractions: Experience fun-filled days with nearby amusement park activities suitable for all ages.
  • Romantic retreats: Relish peaceful moments and intimate strolls along the serene shoreline perfect for couples.
  • Local cultural charm: Explore the relaxed, historical ambience that infuses the neighbourhood with character.
  • Outdoor adventures: Engage in a blend of natural beauty and outdoor activities for a memorable holiday escape.

Popular types of accommodation around Ocean Pines

Welcome to Ocean Pines, Berlin, Maryland, where a blend of coastal charm and relaxed living awaits. Enjoy magnificent ocean views from private holiday homes, cosy apartments, and modern condos. Discover local attractions and scenic experiences, making your stay a memorable retreat. Experience the best in holiday rentals, from ocean pines rentals to peaceful house rentals, ensuring a rejuvenating getaway.

  • Private Holiday Homes: The top choice for visitors, offering spacious and private living environments ideal for families or groups.
  • Condos: A popular option, these self-contained units often come with shared amenities, perfect for a convenient getaway.
  • Apartments: These versatile spaces provide a home-away-from-home experience, suitable for solo travellers and couples.
  • Cottages: Charming and quaint, cottages provide a cosy retreat amidst nature, perfect for a tranquil escape.
  • Villas: Elegant and luxurious, villas offer a premium holiday experience with ample space and upscale features.**

Top attractions near Ocean Pines

Ocean Pines, Berlin, Maryland, offers a delightful escape for those seeking outdoor adventures and romantic beach holidays. Visitors can enjoy the scenic beach and esplanade, perfect for leisurely strolls and relaxation. Families will appreciate the nearby amusement park, while culture enthusiasts can explore the charming local experiences. With its blend of natural beauty and engaging activities, Ocean Pines is an ideal destination for a memorable getaway.

  • Ocean City Boardwalk: A delightful esplanade offering outdoor family and romantic experiences, its ambience enhanced by scenic views, located 10km from Ocean Pines.
  • Ocean City Beach: A charming beach destination with quintessential seaside vibes, positioned 10km from Ocean Pines.
  • Jolly Roger Amusement Park: An exhilarating amusement park providing outdoor and adventurous family fun, situated 8km from Ocean Pines.

Things to do recommended for couples

For a romantic getaway in Ocean Pines, enjoy a sunset stroll along the picturesque beaches of Assateague Island, just a short drive away. Indulge in a candlelit dinner at a charming local restaurant, and take a leisurely bike ride through the scenic trails, soaking in the natural beauty together.

Things to do recommended for families

Families visiting Ocean Pines can enjoy a day at the local family park and explore interactive exhibits at nearby museums, providing a delightful mix of outdoor adventures and educational experiences.

Things to do recommended for groups

Groups visiting Ocean Pines, Berlin, Maryland can enjoy local experiences such as exploring nearby nature trails, engaging in community events and local culinary tours, while appreciating the unique charm of the region.

*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 are journeying with a group, as a family, with your pets, or seeking extended stays, ensure you apply the appropriate filters. Here are some Stayz booking pointers for you.

  • Traveling to Ocean Pines with a group: Consider the amount of bedrooms required, as well as facilities like a fully equipped kitchen or an outdoor area for group get-togethers. Fortunately, you can apply filters for all these options, and more, on Stayz.
  • Traveling to Ocean Pines with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, alongside ensuring access to suitable amenities, like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can greatly enhance your experience.
  • Taking your pets with you to Ocean Pines: For many, a family holiday isn’t complete without their furry companion. If that resonates with you, then explore Stayz properties that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds to ensure everyone feels right at home.
  • Planning for a long term stay visiting Ocean Pines: If you're seeking holiday lets that offer special rates for month-long stays or more, you've come to the right place. With the appropriate filter, you can effortlessly locate and save on monthly rentals. You might also consider including features such as parking, a well-equipped kitchen, or a private pool in your search.

Where to stay near Ocean Pines

Ocean Pines, Maryland offers a delightful blend of serene beach holidays and family-friendly attractions. Enjoy the scenic, outdoor ambience while exploring charming coastal paths and relaxing near the ocean. The local area exudes a relaxed, historical atmosphere with inviting spaces perfect for romantic getaways and family adventures alike.

  • Ocean City: Located a mere 10km from Ocean Pines, Ocean City is a vibrant coastal city renowned for its outdoor activities and family-friendly atmosphere. The famous boardwalk stretches along the beach, offering an array of shops, restaurants, and amusement rides. Visitors can enjoy a day at the beach, explore the local water park, or indulge in delicious seafood at one of the many dining establishments. The stunning esplanade is perfect for leisurely strolls, while the family beach area ensures fun for all ages, making it an ideal destination for a romantic getaway or a family holiday.
  • Isle of Wight: Just 5km away from Ocean Pines, Isle of Wight is a charming island that offers a delightful mix of outdoor adventures and family-friendly experiences. The boardwalk is perfect for leisurely walks, while the local theatre often showcases engaging performances. Golf enthusiasts will appreciate the scenic courses available on the island. Visitors can take in the beautiful views of the bay and marina, creating a picturesque setting for relaxation or exploration, making it a great spot for both romantic escapes and family outings.
  • Glen Riddle: Situated 5km from Ocean Pines, Glen Riddle is a serene neighbourhood that beckons outdoor enthusiasts and families alike. With access to a picturesque boardwalk and well-maintained golf courses, it offers ample opportunities for recreation. The local beach and esplanade are perfect for unwinding or enjoying family activities. The inviting atmosphere of Glen Riddle makes it a lovely choice for a romantic stroll or a fun-filled day with loved ones, ensuring a memorable stay.

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. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

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

Booking with Stayz is a breeze

Are you seeking to make your next journey more cost-effective? Being flexible with your travel dates can lead to substantial savings, as prices often fluctuate. Additionally, opting for a longer stay can also yield noteworthy discounts. To discover a Stayz property that aligns with your budget, utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Planning as easy as it gets

Stayz's cutting-edge Trip Board offers you a dedicated space to plan new adventures, pick up from where you last left off, or manage your existing itineraries. You can easily access properties that you've saved or booked, now organised under Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.stayz.com.au/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 Stayz?
Stayz 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?
Stayz 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 Stayz, 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 Stayz?
To find Ocean Pines holiday rentals with free cancellation, just use Stayz'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, Stayz 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 Stayz?
Stayz'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 Stayz 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. Stayz offers something for every taste and budget, from affordable homes in Ocean Pines to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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 StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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 Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz 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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