Ocean Pines holiday lettings

We found 7,383 holiday rentals — enter your dates for availability

Select from 216 homes, 23 cottages and other holiday rentals in Ocean Pines to find one that's 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:2 Jan - 9 Jan

Image gallery for 10 minutes to Ocean/beaches, stylish, inviting home on a quiet tree-lined street

House Front/Driveway
10 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)

10 minutes to Ocean/beaches, stylish, inviting home on a quiet tree-lined street

Berlin, MD

8% off
Price is £1,823
for 7 nights, 1 home
£260 per night
includes taxes & fees
10 minutes to Ocean/beaches, stylish, inviting home on a quiet tree-lined street

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Frequently asked questions

What is the most popular type of holiday rental in Ocean Pines?
In Ocean Pines, holiday houses are the most popular type of rental, with around 195 available throughout the area. These properties are typically spacious and well-equipped, offering multiple bedrooms, fully equipped kitchens, and comfortable living areas, ideal for families and groups. Many houses also feature outdoor spaces, such as decks or gardens, allowing guests to enjoy the pleasant Maryland weather. Additionally, there are approximately 22 cottages that provide a charming, rustic escape, often with unique architectural details and a cosy atmosphere. For those seeking smaller accommodations, several condos and mobile homes are available, offering a more compact yet comfortable option for travellers.
Are there any beach house rentals in Ocean Pines?
In Ocean Pines, Maryland, there are approximately 245 beach house rentals available, making it a popular destination for holidayers seeking a coastal escape. These rentals are predominantly located in serene neighbourhoods close to the water, providing easy access to the beautiful beaches of the nearby Atlantic coast.
How much does it cost to rent a holiday home in Ocean Pines?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Ocean Pines to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Ocean Pines holiday house rentals?
You can find great discounts on house rentals in Ocean Pines on Vrbo, 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.
Are there any Ocean Pines holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
Can I find long-stay holiday rentals in Ocean Pines?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Ocean Pines for a holiday rental?
The best time to visit Ocean Pines for a holiday rental is during the summer months, particularly in July. This peak season, which runs from June to August, attracts a vibrant crowd seeking fun in the sun, with plenty of opportunities for outdoor adventures and relaxation by the water. Visitors can enjoy activities such as biking, kayaking, and sunbathing on nearby beaches, ensuring a memorable holiday experience.

In July, Ocean Pines offers warm temperatures, typically ranging in the high 20s to low 30s Celsius, creating ideal conditions for enjoying the great outdoors. The area buzzes with life, featuring numerous events and activities, including local festivals and farmers' markets that showcase the region's rich culture and produce.

For those looking to save a bit while still enjoying a lovely getaway, November presents a fantastic alternative. This month is quieter, allowing for a more peaceful exploration of the area's natural beauty and local attractions. The fall foliage can be particularly stunning, providing a picturesque backdrop for leisurely walks and scenic drives.
Are there any remote work holiday rentals in Ocean Pines?
In Ocean Pines, there are numerous remote work-friendly holiday rentals available, with around 210 options to choose from. This charming community in Maryland offers a variety of properties that cater to those looking to blend work and leisure. Many of these rentals come equipped with essential amenities for remote work, including high-speed Wi-Fi, dedicated desks, ergonomic chairs, and even laptop workspaces. Some properties may also feature additional conveniences like computer monitors and safes for keeping valuables secure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Ocean Pines holiday rental?
Book your Ocean Pines holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Ocean Pines home rental booking on Vrbo?
To find Ocean Pines holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Ocean Pines holiday rental prices shown on Vrbo?
Vrbo 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.

More holiday ideas

More holiday ideas