Ocean Pines is a modern community with a great range of contemporary vacation rentals. What's more, the surrounding woodland and nearby water give it that "back to nature" feel.

Top 15 Recommended vacation rentals in Ocean Pines
Find your perfect vacation rental in Ocean Pines from just $172 per night!
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844 beautiful properties from 9 partner websites can be compared in Ocean Pines, with prices starting at $172 a night. By comparing these properties, HomeToGo features the best deals and the most popular accommodations in Ocean Pines.
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Popular Rental Amenities in Ocean Pines
Many of the accommodations include a pool, which makes Ocean Pines a great destination for people looking to make a splash. In addition, properties with pools in Ocean Pines cost, on average, $460 per night. Most of the available properties with pools are hotel room. If you would ideally like to be close to the water, one-third of the properties offering a pool are within 2 miles of the waterfront.
Waterfront Vacation Rentals in Ocean Pines

Family activities in Ocean Pines
Come together as a family in Ocean Pines as you enjoy walking trails, kayaking, and numerous parks, including the waterfront Homer Gudelsky Park.
Or head to the Frontier Town High Ropes Adventure Park, just 20 minutes away from your vacation home. Zip lining, forest canopy obstacle courses, and a theme park are just some of the thrilling attractions here.
Seaside fun at Ocean City
Just ten miles away from Ocean Pines is the lively seaside town of Ocean City, offering classic American coastal fun at its best. Boardwalks, sandy beaches, fairground rides, and family restaurants – Ocean City has the lot.
Ocean city is also where you'll find the Jolly Roger Amusement Park. Part water park, part fairground, this modern theme park has rides and attractions to amuse visitors of all ages.
Information about vacation rentals in Ocean Pines
🏡 Vacation rentals available | 844 rentals |
---|---|
💳 Possible discounts | up to 15% |
🌙 Nightly prices starting at | $172 |
⭐ Popular amenities | Pets allowed, Pool and Internet |
🐾 Pet friendly homes | 219 homes |
🏊 Vacation rentals with pools | 536 homes |
Frequently Asked Questions
What is the typical nightly price for a vacation home in Ocean Pines?
The average accommodation in Ocean Pines is priced at $172 per night. Nightly prices for house rentals are $538 on average. Cottages in Ocean Pines cost on average $398 per night.
How many vacation homes are available to book in Ocean Pines?
There are 844 vacation rentals from 9 providers in Ocean Pines.
What amenities are most popular for vacation homes in Ocean Pines?
Three most popular amenities for vacation home rentals in Ocean Pines include accommodations that have: Pool, Pets allowed, and Internet.
How many vacation homes with pools are there in Ocean Pines?
Choose from 536 vacation rentals available to book in Ocean Pines.
Are pets allowed in vacation homes in Ocean Pines?
Finding a vacation rental in Ocean Pines that allows dogs is easy, with 219 pet-friendly available.
What are the best months to travel to Ocean Pines?
If booking a vacation rental in Ocean Pines, consider that rainy season is usually in March or December, with August often being the driest.
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Top cities to visit
- Cape May
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- Annapolis
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- Edgewater
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