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Ocean Pines Vacation Rentals

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See all 509 deals in Ocean Pines

Our Favorite Vacation Rentals in Ocean Pines

  • 36283 Sunflower Boulevard
     3br Townhouse
    RedAwning
    From
    $455
  • Sandy Pines
     Country House
    Booking.com
    From
    $125
  • NEW LISTING! Spacious, two-story home w/full kitchen, balcony & outdoor fire pit
     5br Home/Apartment
    HolidayLettings
    From
    $308
  • Sunset Island 41 Townhouse
     5br Home/Apartment
    RedAwning
    From
    $800
  • Dockside Retreat
     Country House
    Booking.com
    From
    $114
  • Dog-friendly condo with shared pool plus lake, canal, and golf course views
     3br Home/Apartment
    HolidayLettings
    From
    $241
  • Bay Cove 3
     2br Home/Apartment
    RedAwning
    From
    $258
  • Bayview Beauty
     Country House
    Booking.com
    From
    $105
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Check prices for these upcoming dates

Ocean Pines Vacation Rentals with a Pool

  • 36301 Waterleaf Way
     5br Home/Apartment
    RedAwning
    From
    $693
  • Gullway Villas 2628-202A
     2br Home/Apartment
    RedAwning
    From
    $239
  • Sunset Bay 417
     2br Home/Apartment
    RedAwning
    From
    $235
  • Thunder Island 141D
     2br Home/Apartment
    RedAwning
    From
    $207
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Ocean Pines Vacation Rentals with Wi-Fi

  • 26388 Seabreeze Landing
     3br Townhouse
    RedAwning
    From
    $533
  • Harbour Island 308M
     3br Home/Apartment
    RedAwning
    From
    $427
  • Bimini 106
     2br Home/Apartment
    RedAwning
    From
    $306
  • Our Place At The Beach 105E
     2br Home/Apartment
    RedAwning
    From
    $207
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Ocean Pines Pet-Friendly Vacation Rentals

  • NEW! Ocean Pines House w/ Screened-In Deck & Grill
     3br Home/Apartment
    HolidayLettings
    From
    $340
  • Montego Bay - South Ocean Drive 203
     3br Home/Apartment
    RedAwning
    From
    $217
  • Montego Bay - Peachtree Road 122
     3br Home/Apartment
    RedAwning
    From
    $201
  • Gorgeous Home Bayside OC Resort-Pools,Kayak dock, 5min to beach boardwalk, Golf
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $551
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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.

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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.
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The Weather in Ocean Pines

Rainy days
89 º54
4
84 º32
5
74 º23
7
63 º23
4
58 º1
5
74 º15
2
67 º24
3
74 º28
2
87 º41
10
91 º54
6
91 º52
6
95 º56
2
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

This climate histogram shows you the weather patterns in Ocean Pines. The warmest months in Ocean Pines are May and July, when temperatures reach 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.

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What Expert Travelers Think

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    Whitney WearTravel Better Guide
    Travel Better Guide

  • — Site is easy to use; clean, laid out well, good colors and branding, fun logo and title that connects to the purpose of the brand. The blog, vacation destinations, and rental destinations is a great feature and really make the brand stand apart from other sites!

    Laurelle McVicker
    Laurelle McVickerLaurelle McVicker
    Laurelle McVicker

  • — As a mom of 5 kids who enjoy traveling, I love AllTheRooms! It is quick and easy to find the best deal on lodging that fits our family, in the area we'd like. AllTheRooms really does save you time, money, and hassle.

    Becky
    BeckyKid World Citizen
    Kid World Citizen

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