Ocean Pines Vacation Rentals

Our Favorite Vacation Rentals in Ocean Pines

  • Sandy Pines
     Country House
    Booking.com
    From
    $95
  • Dog-friendly condo with shared pool plus lake, canal, and golf course views
     3br Home/Apartment
    HolidayLettings
    From
    $227
  • Bayview Beauty
     Country House
    Booking.com
    From
    $101
  • Dog-Friendly Berlin Home w/ Pool & Water Access!
     2br Home/Apartment
    HolidayLettings
    From
    $215
  • Cottage on the Cape
     Country House
    Booking.com
    From
    $102
  • OC & bay views, indoor & outdoor pools, balcony.
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $496
  • Family Tides
     Country House
    Booking.com
    From
    $402
  • Charming dog-friendly townhouse just 1 1/2 blocks to the beach w/ shared pool
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $393

Check prices for these upcoming dates

Ocean Pines Vacation Rentals with a Pool

  • Unique waterfront home w/ shared pools, a furnished deck, & a full kitchen
    Excellent4br Home/Apartment
    Airbnb
    From
    $344
  • Eastern Shore Getaway (waterfront w/dock & kayaks)
    Excellent3br Home/Apartment
    Airbnb
    From
    $338
  • Ocean Pines waterfront house
    Excellent5br Home/Apartment
    Airbnb
    From
    $622
  • West OC Luxury Townhome, Close to Everything
    Excellent3br Home/Apartment
    Airbnb
    From
    $418

Ocean Pines Vacation Rentals with Wi-Fi

  • Sea Breeze Hideaway
     4br Home/Apartment
    Airbnb
    From
    $218
  • “The Green Anchor” Charming cabin 6 miles from OC
    ExcellentHome/Apartment
    Airbnb
    From
    $106
  • Ocean Pines Beach House
    Good5br Home/Apartment
    Airbnb
    From
    $224
  • Private Waterfront Apartment Minutes to Ocean City
    ExcellentHome/Apartment
    Airbnb
    From
    $185

Ocean Pines Pet-Friendly Vacation Rentals

  • Large Home with Assateague Island Views near Ocean City, Berlin and Frontierland
    Excellent5br Home/Apartment
    HolidayLettings
    From
    $393
  • NEW! Ocean View Resort Townhome - Bike to Beach!
     3br Townhouse
    HolidayLettings
    From
    $326
  • Dog friendly entire guest suite w/comm pool&marina
    ExcellentHome/Apartment
    Airbnb
    From
    $198
  • Newly renovated! Steps to beach & boardwalk!
    Excellent3br Home/Apartment
    Airbnb
    From
    $133

Ocean Pines Travel Guide

Ocean Pines is a quiet residential community that is located on the waterfront of Eastern Maryland. In the heart of Northern Worcester county, the properties here overlook the beach and offer over nine miles of pleasant coastal walks, in addition to 3,000 acres of woodland.

Things to Do in Ocean Pines

The best things to do in Ocean Pines involve getting outside and into nature. There are many golf clubs in the area that give visitors the chance to perfect their swing and work on their handicap. Taking the 5-mile drive to Ocean City beach is a nice way to spend the afternoon, as is enjoying one of the scenic trails through nearby White Horse Park, Bainbridge Park, and South Gate Pond.

Best Places to Stay in Ocean Pines

Bainbridge and Downtown are the best places to stay in Ocean Pines as they allow visitors to get around easily to the main parks, golf clubs, and other attractions without needing to drive. Those who prefer to spend time on the beach can consider accommodation near the Ocean City boardwalk where vibrant promenades and amusement parks offer fun for all the family.

Best Time to Visit Ocean Pines

The best time to visit Ocean Pines is during the summer months between June and August.

Price and Availability in Ocean Pines

Most expensive
Most availability
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The cheapest day to stay at a vacation rental in Ocean Pines tends to be Tuesday, while the most expensive day tends to be Friday. Vacation homes in Ocean Pines tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Ocean Pines is in July, while the cheapest month is in February. The most popular time to book a vacation rental in Ocean Pines is in the high season in August. Ocean Pines has its low season in November, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Ocean Pines

Rainy days
74° 23°
7
63° 23°
4
58°
5
74° 15°
2
67° 24°
3
74° 28°
2
87° 41°
10
91° 54°
6
91° 52°
6
95° 56°
2
89° 54°
4
84° 32°
5
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

This climate histogram shows you the weather patterns in Ocean Pines. The hottest month in Ocean Pines is May, when temperatures peak at 95 ˚F. The coolest month is December, when temperatures drop to 1 ˚F. The wettest month in Ocean Pines is August with 10.46 inches of rain, while the driest month is May with 1.71 inches of rain.

What Expert Travelers Think

  • — Like the buttons on the calendar which say today, tomorrow - that will make it easy for booking on the road. Website looks great - clean and easy to understand.

    Samantha Wragg
    Samantha WraggCoco Travels
  • — I love how AllTheRooms shows a map with room price tags straight away when you search, it makes it so quick and easy to choose the right hotel, at the right price in the right location. Perfect for those with busy lifestyles! The AllTheRooms website is so user friendly. WiFi. Brilliant!

    Amanda Alston
    Amanda AlstonAmanda Alston
  • — I love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time

    Jeff Campbell
    Jeff CampbellMiddle Class Dad

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