Holiday houses in Ocean Pines

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Quick stats about holiday rentals in Ocean Pines

  • Total holiday rentals

    Explore 320 holiday rentals in Ocean Pines

  • Nightly prices starting at

    Ocean Pines holiday rentals start at $73 AUD per night before taxes and fees

  • Verified guest reviews

    Over 8,440 verified reviews to help you choose

  • Family-friendly holiday rentals

    300 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 100 rentals that welcome pets

  • Holiday rentals with a pool

    170 properties feature pools

  • Rentals with dedicated workspaces

    140 properties have a dedicated workspace

  • Wi-Fi availability

    320 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!

Top-rated holiday rentals in Ocean Pines

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A single-story home sits nestled among lush greenery, featuring a welcoming front porch with a wooden railing. A set of steps leads up to the entrance, flanked by large windows adorned with green shutters, complementing the home's neutral exterior.
Cottage in Ocean Pines
4.9 out of 5 average rating, 199 reviews

Cozy Beach Getaway in the Lovely Ocean Pines North

Welcome to our Cozy Beach Getaway!! ☀️🌊👙⛱️🐚🏖️🌞🌅⛅️ This beautiful and peaceful home is located in Ocean Pines North. 3 bedrooms, 2 bathrooms. Peaceful front porch and back deck. 🏡🏝️ Whether you’re looking for a summer family vacation, girls weekend getaway, or just a break from reality, this is the perfect place! Washer/dryer 🧺, two smart TV’s 📺, driveway fits 4 cars comfortably 🚗. Enjoy the hustling city of Ocean City during the day and stay in the tranquility and peaceful Ocean Pines at night! 🏖️💞☀️

Top Guest favourite
A single-story home with a well-kept exterior is surrounded by trees, providing a serene setting. A covered porch with railings welcomes guests, while a gravel driveway leads to the entrance. The property features a reliable trash can and is nestled within a natural landscape.
Home in Ocean Pines
4.98 out of 5 average rating, 46 reviews

Tranquil Waters, OceanPines, 3 br, Dog Friendly

Peaceful Coastal Getaway – Dog Friendly! Relax with the whole family at this peaceful beach retreat! This 1,500 sq. ft. home away from home is perfect for a laid-back vacation near the shore. Featuring 3 bedrooms (King, Queen, and 2 Twins), this home is spotlessly disinfected before each stay and includes a full linen package for your comfort and convenience. Enjoy a free parking pass to the Ocean Pines Beach Club on 49th Street, and make the most of the beautiful outdoor space—a low fenced-i

Top Guest favourite
An A-frame structure is set amidst lush greenery, featuring a welcoming front porch with steps leading up to the entrance. Two bicycles are positioned nearby, and vibrant flowers adorn the edges. Sunlight filters through the leafy trees, enhancing the natural surroundings.
Home in Ocean Pines
5 out of 5 average rating, 53 reviews

hi-A-tus A-frame

Charming A-frame nestled in the heart of OP. Open floor plan, softest sheets, flat screen TVs, high speed WiFi, in an amenity filled community surrounded by multiple beaches. 10 min from OC & 15 min from Assateague! Sleeps 4 comfortably. Perf for 4 adults or fam. Must be 25 yrs old. Enjoy all that OP has to offer including 5 pools, multiple playgrounds, yacht club & farmers market. Weekly rental during the high season (6/6 - 8/29), Sat check-in/Sat check-out only! If you book diff, we'll cancel

Top Guest favourite
A cozy living area features a white couch and two accent chairs with a leaf pattern. A glass coffee table sits on a woven area rug. Large sliding doors provide a view of the outdoor patio, framed by greenery and water, enhancing the space's natural light.
Guest suite in Ocean Pines
4.95 out of 5 average rating, 407 reviews

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!

Top Guest favourite
A serene waterfront scene is captured at sunset, with vibrant colors reflected in the calm water. A charming building with large windows is illuminated, surrounded by lush trees, and boats are docked along the waterfront, creating a peaceful atmosphere.
Condo in Ocean Pines
4.97 out of 5 average rating, 218 reviews

Water view at Ocean Pines Yacht Club 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

Top Guest favourite
A cozy living area features a light gray sofa adorned with decorative pillows and a small blue ottoman. Natural light brightens the space, showcasing art on the walls and a dining area in the background, complemented by a wooden table and chairs.
Home in Ocean Pines
4.87 out of 5 average rating, 103 reviews

Home Away from Home , Pet friendly retreat

Welcome to Ocean Pines Getaway, Enter home through a beautiful covered porch with swing for two and lovely seating area. This sweet home has 3 bedrooms & 2 full baths. A fully stocked kitchen , with eat in breakfast nook, Also proper dining room plenty of seating for family Cozy living room with working fireplace. All season sunroom plenty of seating, pub table & bar. Doggie door in sunroom large enough for 100 lb dog, leads to fenced in backyard. $100 pet fee and $125 linens & bath towels.

Top Guest favourite
The exterior of a single-story house is visible, featuring a spacious front porch with white railings. Large windows allow natural light to enter, while a driveway provides parking for two vehicles. A wooded area surrounds the property, enhancing its peaceful setting.
Home in Ocean Pines
4.98 out of 5 average rating, 145 reviews

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!

Top Guest favourite
The living area features large sliding doors that open to a porch with stunning bay views during sunset. A neutral-colored couch and a cozy chair create a welcoming space. A wooden dining table complements the serene atmosphere, illuminated by the warm glow from the setting sun.
Townhouse in Ocean City
4.97 out of 5 average rating, 520 reviews

Edgewater Escape - Luxury Bayfront Loft with Porch

You've never seen waterfront like this. Welcome to Edgewater Escape, a luxury bayfront loft apartment that hangs entirely over the bay on 7th street in downtown Ocean City. Sit on the bay front porch or hang out inside and watch boats, dolphin, birds, and sometimes even seals swim by within feet of the porch. The loft has a roomy king sized bed and the downstairs couch pulls out into a comfy queen bed. Recently renovated, it comes fully equipped for your big trip or quiet staycation :)

Guest favourite
A waterfront backyard features sandy areas lined with a white picket fence. A picnic table is positioned on the beach, facing the calm waterway. Houses are visible along the banks, framed by trees and distant structures under a soft evening sky.
Home in Ocean Pines
4.91 out of 5 average rating, 201 reviews

Waterfront Beach Home in the Ocean City, MD Area

There is room for 8 adults (plus 2 kids). Located in the premiere seaside community in the Ocean City area, Ocean Pines, this wonderful waterfront home provides amazing views both day and night. The open floor plan provides guests with lots of room to socialize and bond, but also has secluded bedrooms that provides needed privacy. The outdoor living area is to die for. Sit back and watch the sun set over the canal while you catch up with friends or loved one. Use our bikes!

Top Guest favourite
A bright, open kitchen area is visible, featuring modern appliances and a spacious countertop. Large windows allow natural light to fill the room. A comfortable chair sits beside a decorative rug, while a sleek ceiling fan contributes to the airy atmosphere.
Guest suite in Ocean Pines
4.99 out of 5 average rating, 138 reviews

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.

Top Guest favourite
Vibrant orange and yellow lilies are in full bloom, positioned in the foreground along a pathway. The path leads towards a waterfront area, with chairs visible in the background. A clear sky and soft sunlight enhance the peaceful ambiance of the setting.
Townhouse in Ocean City
4.96 out of 5 average rating, 47 reviews

Bayfront - Walk to Beach & Boardwalk - King Bed

Welcome to our Home Beach Resort! Just a 5-minute walk to Ocean City Beach, boardwalk, bars, restaurants, and amusement parks. 🌅 Bayfront Views – Enjoy stunning sunrises from the master bedroom and sunsets on the bay. 🏡 Comfort & Convenience – Fully furnished home with a private gated boardwalk. 🎣 Outdoor Fun – Fish and crab right in front of the house! ☕ Modern Amenities – Fully equipped kitchen, Keurig coffee maker, WiFi-6. Book now for the ultimate Ocean City getaway!

Superhost
Guesthouse in Ocean Pines
5 out of 5 average rating, 4 reviews

Coastal Retreat near the beach

Kick back and relax in this calm, stylish space just 15 minutes from Ocean City MD beaches. The unit has marsh and water views of Assawoman Bay/Manklin Creek. Located across the bay from Ocean City , MD you are close to the action but can retreat back to a quiet sanctuary when you are looking for some relaxation away from the beach crowds. If you like nature, frequent visitors include, deer, fox, blue heron, egrets, bald eagles, owls and many other birds.

Popular amenities for Ocean Pines holiday rentals

When is the best time to visit Ocean Pines?

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Avg. price$245 AUD$241 AUD$234 AUD$261 AUD$294 AUD$344 AUD$399 AUD$395 AUD$313 AUD$286 AUD$252 AUD$260 AUD
Avg. temp3°C4°C7°C13°C18°C23°C26°C24°C21°C15°C9°C5°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.

Destinations to explore

  1. Airbnb
  2. United States
  3. Maryland
  4. Worcester County
  5. Ocean Pines