Holiday houses in Ocean Pines
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Top-rated holiday rentals in Ocean Pines
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House with Fire Pit + Private Yard near Ocean City
Skies of Blue in Ocean Pines offers a 1400 sq ft spacious beach getaway for the entire family. With a bright open floorplan and 3 large bedrooms (King, Queen, 2 Twins + Full), this newly renovated home will meet all your vacation needs. The huge and private backyard is perfect for entertaining or relaxing, with a large deck, firepit, grill, sunroom, and a fenced yard. The house is just 7 miles from the shores of Ocean City and comes with a free beach parking pass at the OP Beach Club (49th ST).
Ocean Pines, Waterfront Oasis
Beautiful waterfront home! Park two boats. "Endless Summer" is on the canal. Located on the St Martins River in Ocean Pines. Centrally located, close to downtown Ocean City, MD, "the boardwalk", bustling West OC and historic Berlin, MD. Explore Assateague Island, Del. beaches, all just a short drive in the amenity filled [pools, golf, pickle ball, tennis, trails and parks] OP community. Linens, cleaning team & beach club parking included. Must be 25 or older or military service. No pets.
Salty Serenity
Relax and recharge at our cozy 3 bed/2 bath home in Ocean Pines, a peaceful community near Ocean City, MD. Enjoy bikes, kayaks, and a fire pit in the large backyard, or use the pools, marina, yacht club, and golf course in the neighborhood. Beach parking at the Ocean Pines Beach Club in Ocean City is included. You can explore the boardwalk, casino, outlets, and the many nearby restaurants. Or, visit Berlin, or see the wild horses at Assateague Island. Come experience all the area has to offer!
Stunning private waterfront suite
Welcome to your cozy getaway with stunning water views from every room! This sweet 2-bedroom, 1-bath suite boasts a private entrance, a living room, and a cute kitchenette. Nestled in a peaceful, family-friendly neighborhood, you'll have year-round access to swimming pools, a golf course, tennis courts, a Yacht club, and lovely parks nearby. Only a quick 10-minute drive lands you on the sandy beaches and lively Boardwalk of Ocean City. Park in the driveway and step into your own private escape!
OC Gateway: Modern 4BR/2.5BA home (dog friendly)
Have fun with the whole family at our stylish Ocean City-convenient home! This wooded beach house boasts many modern upgrades including a beautiful kitchen with gas range, large flat panel televisions in almost every room, a washer and dryer, and even a Wii video game system in the living room! Queens in 3 bedrooms and a bunk bed with trundle in the 4th! Finally, enjoy all the amenities of Ocean Pines including access to 5 pools, a private OC beach club (w/pool!), and much more! Lic. No. 4586
Ocean Pines marina view condo
Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included
Camelot
HIGHEST RATED HOUSE IN OCEAN PINES! CHECK OUT OUR AMAZING GUEST REVIEWS :) Jumpstart your ultimate beach getaway at this impressive 3-bedroom, 2-bathroom retreat house! Complete with amenity-packed living spaces with vaulted ceilings and a serene location, you’ll never hunger for entertainment at this family friendly home. Grill out on the patio, roast marshmallows by the fire pit, tee off at a nearby golf course, or enjoy some retail therapy at Outlets Ocean City! A short drive to the beach!
Oceans End Waterfront Retreat
Escape to a serene waterfront haven! This two-story home in Ocean Pines offers tranquil water views and endless relaxation. Enjoy the private dock for fishing, kayaking, relax with outdoor dining, or fire up the grill. Inside, vaulted ceilings and cozy furnishings surround you, while the fireplace adds warmth on cool evenings. Just minutes from trails, pools, and beach access, playground and farmers market every Saturday! Golf and yacht club with live music in community! 15 mins to OCMD!
Updated 3 Bedroom 2 Bathroom Home - Ocean Pines
Beautifully updated and recently renovated, rancher on a great street in Ocean Pines perfect for families and adults looking for a relaxing stay. We offer 3 bedrooms and 2 bathrooms on one level, with new large flat screen TV's, stainless appliances, and everything you'll need for your stay. We have a large driveway and a screened patio. Ocean Pines boasts over a dozen parks and walking trails, a public Yacht Club, 5 pools, 2 marinas, and a championship golf course - 10 min to the beach!
Serene OP cottage perfect for families!
Welcome to our Peaceful Pines Family Retreat located in the amenity rich community of Ocean Pines! Whether you are looking for a little R&R or seeking some outdoor adventure, you can enjoy it all just minutes from our cozy, inviting and updated coastal cottage. Our home is located just 8 miles from Ocean City, 7 miles from Berlin (voted America’s Coolest Small Town) 13 miles to Assateague State Park and 2.6 miles to Ocean Downs Casino among many other attractions. Rental Lic # 4033
Newly built bright and airy guest suite!!!!
FREE oceanfront parking pass with bookings. 2nd floor private suite with parking, patio/firepit, and self check-in private entry. We are located just minutes from the Ocean City beaches, quaint small town of Berlin, Ocean Downs Casino, Assateague, Windmill Creek Winery, restaurants, and outlets. Enjoy neighborhood amenities such as a waterfront Yacht Club with restaurant and live music (seasonal), golf, farm market, playgrounds, 5 pools/fee, (no pool on property) racquet club.
OceanPinesFamilyBeachRetreat~JettdTub~KingBed~Golf
Immediate removal of stress at the front door. Being nestled in a marina’s serene waterfront & nature park is good for the soul. Relax in a jetted tub after a sun filled day & an al fresco meal on a back porch with charming outdoor dining. An open concept main level features large windows & comfortable seating through the entire property. 2 full bathrooms upstairs & a king sized bed provide maximum comfort & outdoor living on 2 balconies. Additional fees for pools, pets may apply.
Popular amenities for Ocean Pines holiday rentals
Stay near Ocean Pines's top sights
Other great holiday rentals in Ocean Pines
Waterfront Vacation Home in Ocean Pines
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Beachin' it in Ocean Pines
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Coastal Oasis in Ocean Pines
Ocean Pines Chalet
When is the best time to visit Ocean Pines?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $260 AUD | $244 AUD | $251 AUD | $261 AUD | $295 AUD | $344 AUD | $399 AUD | $395 AUD | $314 AUD | $286 AUD | $253 AUD | $260 AUD |
| Avg. temp | 3°C | 4°C | 7°C | 13°C | 18°C | 23°C | 26°C | 24°C | 21°C | 15°C | 9°C | 5°C |
Frequently Asked Questions
What are the best places to stay in Ocean Pines?
Ocean Pines has a range of vacation rentals, including homes with woodland views and residences near community parks. Many visitors choose family-friendly neighborhoods or rentals with access to nearby golf and swimming amenities.
What are the best things to do in Ocean Pines with kids?
Families often explore local parks, play at community playgrounds, or visit nature trails. Around Ocean Pines, miniature golf and outdoor pools are frequently suggested for younger travelers.
What are some of the best things to do in Ocean Pines?
In Ocean Pines, you can explore scenic walking trails, enjoy boating along waterways, or experience local farmers markets. Golf and community events are also popular throughout the year.
How is the weather in Ocean Pines?
Ocean Pines has cool winters around 28–46°F (-2–8°C) and warm, humid summers near 66–87°F (19–31°C). Spring and fall bring milder temperatures and comfortable outdoor weather.
When is the best time to visit Ocean Pines?
Late spring through early fall is often recommended for Ocean Pines, when temperatures are warmer and outdoor activities are in full swing. Many visitors enjoy local festivals and family events during these months.
What are the best places to visit in Ocean Pines?
Ocean Pines has locally loved parks, nature trails, and marinas. The community center and weekly farmers markets draw both residents and visitors for social gatherings and local flavors.
What are some hiking trails in Ocean Pines?
You can explore woodsy paths through community parks and greenways, where many visitors enjoy peaceful walks and birdwatching. Nearby nature preserves often have gentle, family-friendly trails.
What are some family activities we can do in Ocean Pines?
Popular family activities in Ocean Pines include outdoor swimming pools, playground visits, and bike rides through local park areas. Seasonal craft fairs and farmers markets provide opportunities for all ages to connect.
What are some of the best day trip ideas from Ocean Pines?
Ocean Pines is located near coastal beaches, wildlife refuges, and small towns known for boardwalks and maritime history. Many travelers plan outings to regional amusement parks or nature centers.
Are there any pet friendly accommodations available in Ocean Pines?
Many vacation rentals in Ocean Pines are pet friendly, especially homes near walking paths and parks. When booking, it is common to find stays that accommodate furry companions.
What are some local tips for visiting Ocean Pines?
Pack layers, as temperatures can shift between breezy mornings and sunny afternoons. Bring bikes or comfortable shoes to explore the neighborhood’s paths, and check for community events at the recreation center or farmers market.
What is Ocean Pines known for?
Ocean Pines is known for its tree-lined neighborhoods, extensive network of parks, and community-centered activities. Access to outdoor recreation and a welcoming atmosphere draw many repeat visitors.
What are the best hidden gems to explore in Ocean Pines?
Locals often mention quiet neighborhood gardens, lesser-known nature trails, and seasonal art or craft fairs. Small marinas and dock areas provide peaceful spots to unwind near the water.
What are the best foods to try in Ocean Pines?
Ocean Pines has a range of local flavors, often highlighting fresh seafood such as Maryland blue crab and seasonal fish. Farmers markets feature regional produce, homemade baked goods, and traditional coastal recipes.
What should I bring for a trip to Ocean Pines?
Bring comfortable walking shoes, swimwear for pools or beaches, and layers for cool evenings even in summer. Rain gear and a reusable water bottle are handy for spontaneous outdoor activities.
What is the nightlife in Ocean Pines like?
Nightlife in Ocean Pines is mostly low-key, with neighborhood bars, community events, and live music at local venues. Many visitors unwind at casual restaurants or join in on outdoor summer gatherings.
What are the most popular events or festivals in Ocean Pines?
Ocean Pines has a variety of community events throughout the year, such as summer concerts, farmers markets, and seasonal craft fairs. Memorial Day and Labor Day weekends often feature special gatherings and celebrations for residents and visitors.
Are there family friendly vacation rentals in Ocean Pines?
Many vacation rentals in Ocean Pines are designed for families, including homes with multiple bedrooms or proximity to parks and pools. Features like full kitchens and outdoor space are commonly found for family comfort.
Quick stats about holiday rentals in Ocean Pines
Total holiday rentals
Explore 310 holiday rentals in Ocean Pines
Nightly prices starting at
Ocean Pines holiday rentals start at $44 AUD per night before taxes and fees
Verified guest reviews
Over 8,630 verified reviews to help you choose
Family-friendly holiday rentals
280 properties offer extra space and kid-friendly amenities
Pet-friendly accommodation
Find 100 rentals that welcome pets
Holiday rentals with a pool
160 properties feature pools
Rentals with dedicated workspaces
140 properties have a dedicated workspace
Wi-Fi availability
300 of Ocean Pines holiday rentals include Wi-Fi access
Popular amenities for guests
Guests love Self check-in, Gym and BBQ grill across Ocean Pines rentals
4.8 Average rating
Ocean Pines stays are highly rated by guests—averaging 4.8 out of 5!
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