Ocean Pines Vacation Rentals

Our Favorite Vacation Rentals in Ocean Pines

  • 36283 Sunflower Boulevard
     3br Townhouse
    RedAwning
    From
    $411
  • Sandy Pines
     Country House
    Booking.com
    From
    $155
  • Spacious, two-story home w/full kitchen, balcony & outdoor fire pit
     5br Home/Apartment
    HolidayLettings
    From
    $307
  • SUNSET ISLAND 50
     6br Home/Apartment
    RedAwning
    From
    $969
  • Dockside Retreat
     Country House
    Booking.com
    From
    $149
  • Dog-Friendly Berlin Home w/ Pool & Water Access!
     2br Home/Apartment
    HolidayLettings
    From
    $221
  • 36301 Waterleaf Way
     5br Home/Apartment
    RedAwning
    From
    $678
  • Bayview Beauty
     Country House
    Booking.com
    From
    $140

Check prices for these upcoming dates

Ocean Pines Vacation Rentals with a Pool

  • Thunder Island A-19
     2br Home/Apartment
    RedAwning
    From
    $545
  • BAY PRINCESS 116
     2br Home/Apartment
    RedAwning
    From
    $559
  • 26388 Seabreeze Landing
     3br Townhouse
    RedAwning
    From
    $431
  • OUR PLACE AT THE BEACH 207 H
     2br Home/Apartment
    RedAwning
    From
    $500

Ocean Pines Vacation Rentals with Wi-Fi

  • Wild Bay Landing 2
     3br Home/Apartment
    RedAwning
    From
    $1,000
  • Gullway Villas 2628-202A
     2br Home/Apartment
    RedAwning
    From
    $205
  • KING GEORGE CONDO 710D
     3br Home/Apartment
    RedAwning
    From
    $634
  • Harbour Island 302L
     2br Home/Apartment
    RedAwning
    From
    $228

Ocean Pines Pet-Friendly Vacation Rentals

  • Ocean Pines House w/ Screened-In Deck & Grill!
     3br Home/Apartment
    HolidayLettings
    From
    $331
  • Waterfront West Ocean City Home w/ Skyline View!
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $328
  • Gorgeous Home Bayside OC Resort-Pools,Kayak dock, 5min to beach boardwalk, Golf
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $551
  • Cozy Millville Home w/Pool Near Bethany Beach!
     4br Home/Apartment
    HolidayLettings
    From
    $500

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
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
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
68° 11°
4
63° 13°
4
63° 18°
4
80° 29°
4
92° 44°
3
94° 48°
4
100° 60°
2
91° 58°
4
91° 47°
4
94° 40°
6
71° 21°
2
64° 19°
4
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Ocean Pines. The hottest month in Ocean Pines is June, when temperatures peak at 100 ˚F. The coolest month is December, when temperatures drop to 11 ˚F. The wettest month in Ocean Pines is March with 6.39 inches of rain, while the driest month is February with 1.85 inches of rain.

What Expert Travelers Think

  • — When I first opened up the AllTheRooms.com site, I was impressed right away... When I’m traveling, I don’t like to waste time searching multiple engines for accommodations, it gets overwhelming and frustrating fast. I want a unique, comfortable stay for the best deal

    Kaelin
    KaelinKindly Kae
  • — I love AllTheRooms because it enables me to compare a range of providers in just one search. I'd normally spend time checking prices across a range of platforms by visiting different websites one-by-one, so this helps me to save time on my accommodation searches while planning my upcoming trips

    Kacie Morgan
    Kacie MorganThe Rare Welsh Bit
  • — 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

Vacation Rentals in Ocean Pines

At AllTheRooms.com we have vacation rentals from all of the leading providers - Airbnb, Priceline, RedAwning and others. We have 466 vacation rentals, hotels and other accommodation types in Ocean Pines ranging from cheap options to luxury places to stay. A trip to Ocean Pines can be budget-friendly - our cheapest price rental is available at $27 a night. A typical accommodation in Ocean Pines costs on average $193 a night.

Those looking to get some work finished during their trip to Ocean Pines can pick from 142 places to stay that have WiFi. 8 of our accommodations include a breakfast in the price. Fitness addicts can get a workout in during their stay by choosing from 34 accommodations that have gyms. If you are driving to Ocean Pines, you'll want to pick from 152 places to stay that provide parking. We have 76 accommodations that have a pool or jacuzzi.

If you're traveling with your best friend, then be sure to choose one of the 38 pet-friendly accommodations available.

We combine a wide variety of Ocean Pines accommodations including vacation rentals, home stays, hostels and other unique places to stay into one easy search. We show results from more than 3 providers, including 145 places to stay from Airbnb, 6 accommodations from Priceline and 3 places to stay from RedAwning.

291 accommodations in Ocean Pines have been reviewed; 80% are rated excellent or good. You can instantly book any of 256 places to stay right now.

Destinations near Ocean Pines

  • Ocean City6,339 Properties
  • Oakland2,283 Properties
  • McHenry1,768 Properties
  • Swanton1,399 Properties
  • Annapolis1,190 Properties
  • Baltimore1,138 Properties
  • Bethesda587 Properties
  • Silver Spring441 Properties
  • Frederick402 Properties
  • Cambridge370 Properties
  • Rockville338 Properties
  • Berlin335 Properties
  • Gaithersburg305 Properties
  • Oxon Hill293 Properties
  • Laurel283 Properties
  • Columbia274 Properties
  • Salisbury254 Properties
  • Hanover234 Properties
  • Aberdeen201 Properties
  • Fort Washington193 Properties
  • Easton187 Properties
  • Takoma Park185 Properties
  • Stevensville168 Properties
  • Hyattsville154 Properties
  • Chestertown147 Properties
  • College Park90 Properties
  • St. Michaels81 Properties
  • North Beach57 Properties
  • Mount Rainier52 Properties
  • Accokeek45 Properties
  • Lusby40 Properties
  • Chesapeake Beach40 Properties
  • West Ocean City18 Properties
  • Emmitsburg10 Properties