Holiday houses in Ocean Pines
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Quick stats about holiday rentals in Ocean Pines
Total holiday rentals
Explore 350 holiday rentals in Ocean Pines
Nightly prices starting at
Ocean Pines holiday rentals start at $138 NZD per night before taxes and fees
Verified guest reviews
Over 9,110 verified reviews to help you choose
Family-friendly holiday rentals
330 properties offer extra space and kid-friendly amenities
Pet-friendly accommodation
Find 100 rentals that welcome pets
Holiday rentals with a pool
190 properties feature pools
Rentals with dedicated workspaces
150 properties have a dedicated workspace
Wi-Fi availability
350 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.
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! 🏖️💞☀️
Updated Ocean Pines Getaway w Fire Pit, Grill + Be
Relax in this beach‑themed 3BR home with a loft in Ocean Pines, just 7 miles from the Ocean City beaches. Located at 865 Ocean Parkway, this spacious retreat features front and back decks, a gas fire pit, and a gas grill. The layout includes a king and queen bedroom downstairs, a full bedroom upstairs, and a loft lounge with queen sleep sofa, and a desk. Enjoy 24‑hour self check‑in, parking for 3 vehicles, an updated kitchen, full‑size washer/dryer, 4 smart TVs, outdoor fire pit trailer parking
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!
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
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.
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!
Waterfront w/Dock, Rooftop Terrace & 2 Kings
Enjoy stunning views from every room in this bayside beauty located in the peaceful Ocean Pines community just 9 miles from the beach and OC boardwalk. Designer finishes throughout, you'll find everything you need to enjoy a family or small group getaway. *We do not allow smoking or pets. *Saturday check-in with a 7 night minimum stay requirement from July-August. *We are located in a quiet, residential neighborhood. Please consider this when booking. *We do not supply sheets and towels.
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!
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.
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.
Summer By The Sea
Located on a quiet cul de sac, this cute 3 bedroom home is a perfect getaway. Enjoy the fun and excitement of Ocean City with its beach, boardwalk, restaurants and nightlife, and then retreat to the quiet relaxation of Ocean Pines. A movie theater, outlets, and fabulous eateries in West OC. Assateague Island National Seashore is only minutes away. Ocean Pines offers a state of the art public golf course, pool access(for a fee ) playgrounds, and beach club .
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
Salty Serenity
Birdies by the Bay | Waterfront & Private Dock
Peace in the Pines- 3BD, 2BA w/ Beach Club Pass
Family Oasis - 4BR 3BA on Golf Course
Private, pet-friendly, w/game room & new kitchen
Cabin in the Pines I Luxury Touches + EV Charging
Cozy home 8 miles from OCMD *Beach Pass Included*
Coastal Oasis in Ocean Pines
When is the best time to visit Ocean Pines?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $291 NZD | $286 NZD | $277 NZD | $310 NZD | $349 NZD | $408 NZD | $473 NZD | $468 NZD | $372 NZD | $339 NZD | $299 NZD | $308 NZD |
| 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.
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