Holiday rentals in Ocean Pines
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Top-rated holiday rentals in Ocean Pines
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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! 🏖️💞☀️
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
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
Peaceful Marina Village Condo with Marina View
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!
Newly Renovated Ocean Pines Cottage
Completely remodeled beach home with brand new furnishings in Ocean Pines. Open concept living on main level with beautiful well-equipped kitchen, seating for 10 total at island/dining table and a relaxing living room. Off the hallway is the king bedroom and separate full bathroom with bathtub. Spacious mud/laundry room with beach chairs, umbrella and wagon available for use. Open loft area upstairs with arcade game, lounging area, 2 additional bedrooms and full bath with stand-up shower.
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!
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.
Cozy beach home away from home!
Welcome! Come enjoy a cozy experience at this centrally located home in the desired Ocean Pines Community! This home is near the playground and allows access to the on-site golf course, five pools (including indoor pool!) tennis courts, and marina for a small fee. Fun in the sun awaits 15 minutes away in downtown Ocean City, where you can stroll the boardwalk, lounge on the sand, or hit the amusement park. Plenty of restaurants, grocery stores and shopping within 15 minutes.
Peaceful Beach Cottage - Sanitized & WiFi!
Fully renovated clean, sanitized, quaint house in a quiet neighborhood minutes from the beach/ocean! Community offers many amenities such as pools, restaurants, playgrounds, etc. Have peace and quiet while only being minutes from the beach and main OC drag. Very close to the casino! Voted "#1 Safest Neighborhood in Maryland!" *June-August we only accept 7 day rentals with a Saturday check in* *Memorial & Labor Day weekends have 3 night minimum with Fri check in*
Sweet Retreat
Sweet Retreat is conveniently located in Ocean Pines, Maryland. The premiere residential and resort community of Ocean Pines is located eight miles inland from the ocean resort town of Ocean City. Ocean Pines has over 9 miles of waterfront property and 3,000 acres of wooded areas. Community amenities include beaches, a yacht club, golf course, community center, a Beach Club Pool and other community pools. Passes are available at ocean Pines Association.
Popular amenities for Ocean Pines holiday rentals
Stay near Ocean Pines's top sights
Other great holiday rentals in Ocean Pines
Coastal Retreat: River View & Pine Haven
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Stubbe's Beach House, Home in Ocean Pines, MD
Ocean Pines Fun – Arcade, Pools & Near O.C. Beach
Family Oasis - 4BR 3BA on Golf Course
122 Ocean Parkway, Ocean Pines, MD
Charming cul-de-sac House just minutes from OC.
Ocean Pines, Waterfront Oasis
When is the best time to visit Ocean Pines?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $228 SGD | $214 SGD | $221 SGD | $229 SGD | $259 SGD | $302 SGD | $351 SGD | $347 SGD | $275 SGD | $251 SGD | $222 SGD | $228 SGD |
| 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 $38 SGD 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 & child-friendly amenities
Pet-friendly holiday rentals
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
Wifi availability
300 of Ocean Pines holiday rentals include wifi 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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