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Holiday rentals in Ocean Pines

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Top-rated holiday rentals in Ocean Pines

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

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Top 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, 194 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
Home in Ocean Pines
5 out of 5 average rating, 22 reviews

Whimsical Willow l Beach Club Pass and No Pet Fee

Discover this charming 3-bedroom home! With wood floors throughout, it features a king master suite, a queen bedroom, and a kids’ room with a twin-over-full bunk. Enjoy a fully stocked kitchen, fast WiFi, a screened-in porch, and a jetted tub for ultimate relaxation. Perfect for families or dual-family stays! Explore Ocean Pines or take a quick 10-minute drive to Ocean City for endless fun. Included is the Beach Club Parking Pass! Plus- A local manager is here to ensure everything goes smoothly.

Top guest favourite
A scenic collage features various images: a tranquil beach sunset, a lush golf green with a white sand trap, a wooden pier stretching over gentle waves, wild horses running along the shore, and a charming screened porch nestled among tall trees.
Home in Ocean Pines
4.97 out of 5 average rating, 60 reviews

Ocean Pines-OCMD Bliss at the Beach- Sat. to Sat.

Welcome to Bliss at the Beach, our charming 3br, 2ba home nestled in the desirable, beloved Ocean Pines community. Loved for its safe, quaint, family friendly neighborhoods. Find yourself less than 15 minutes away from the beautiful beaches and vibrant shopping, dining and boardwalk district of Ocean City. Enjoy the ease of the prepaid parking at the Ocean Pines Beach club on 49th street, just unload the family and walk on the beach!! Summer months Bliss is a 7-night minimum to guests 25+older

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, 400 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.
Apartment in Ocean Pines
4.97 out of 5 average rating, 214 reviews

Ocean Pines Getaway 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

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, 141 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
An open-concept living area features a well-equipped kitchen with modern appliances and a dining table surrounded by blue chairs. A spacious seating area is visible, leading to a staircase that ascends to an upper loft with a railing overlooking the main level.
Home in Ocean Pines
4.96 out of 5 average rating, 117 reviews

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.

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, 196 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, 135 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.

Superhost
An aerial view of a marina with multiple boats docked along a well-maintained pathway. The surrounding residential community and parking area are visible, as sunlight reflects off the peaceful water, highlighting the scenic environment.
Townhouse in Ocean Pines
4.89 out of 5 average rating, 95 reviews

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.

Guest favourite
A modern kitchen features light grey cabinetry and stainless steel appliances. A round table is set for dining, accompanied by stylish metal chairs. Natural light filters through the window, enhancing the warm, inviting layout that connects seamlessly to adjacent living spaces.
Home in Ocean Pines
4.85 out of 5 average rating, 137 reviews

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*

Top guest favourite
A cozy living area presents a light brown couch adorned with colorful cushions and a decorative throw. Two accent chairs sit across from the couch, positioned on a patterned area rug. Natural light filters through sheer curtains covering a large window, illuminating the space.
Home in Ocean Pines
4.97 out of 5 average rating, 105 reviews

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

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Ocean Pines's top sights

GlenRiddle Golf Club

28 locals recommend

Ocean Pines Golf Club

32 locals recommend

River Run Golf Club & Community

17 locals recommend

Other great holiday rentals in Ocean Pines

Guest favourite
The exterior of a three-bedroom home is showcased amidst tall pine trees. A gravel driveway leads to a garage, while two blue chairs are positioned on the front steps by the entrance, inviting relaxation in the natural surroundings.
Home in Ocean Pines
4.95 out of 5 average rating, 56 reviews

Coastal Retreat: River View & Pine Haven

Guest favourite
A light-colored home is featured, set against a backdrop of trees. The large front window allows natural light to enter the living space. A gravel driveway leads up to the entrance, with a small porch and railing providing access to the front door.
Home in Ocean Pines
4.85 out of 5 average rating, 53 reviews

Amazing and peaceful family fun 4 bedroom home

Top guest favourite
A tranquil waterfront scene captures a canal-side home surrounded by lush greenery. A private boat slip is visible alongside the property, accommodating boats up to 23' long. The sun-filled exterior features a light-colored facade and a cozy patio, enhancing the serene atmosphere.
Home in Ocean Pines
5 out of 5 average rating, 21 reviews

Waterfront Vacation Home in Ocean Pines

Guest favourite
A deck with a metal table and chairs overlooks a serene canal. Boats are docked nearby, while charming homes line the opposite bank, surrounded by lush trees. The clear blue sky reflects the tranquil atmosphere of the waterfront setting.
Home in Ocean Pines
4.97 out of 5 average rating, 38 reviews

WHAT DAY IS IT???????

Guest favourite
The cottage exterior is framed by tall trees, showcasing a welcoming entrance with a deck and steps leading up to a door. The light-colored siding and contrasting teal door create a fresh appearance. Surrounding landscaping includes a gravel path and shrubs, providing a natural setting.
Home in Ocean Pines
4.82 out of 5 average rating, 143 reviews

122 Ocean Parkway, Ocean Pines, MD

Guest favourite
A spacious sectional sofa occupies a corner of the living room, adorned with decorative pillows featuring ocean-themed designs. Soft, neutral-colored walls enhance the airy feel of the space, while sunlight filters through the nearby windows, creating a bright and inviting environment.
Home in Ocean Pines
4.88 out of 5 average rating, 41 reviews

Charming cul-de-sac House just minutes from OC.

Guest favourite
Home in Ocean Pines
4.9 out of 5 average rating, 40 reviews

Cozy Stay by the Bay

Guest favourite
Home in Ocean Pines
4.98 out of 5 average rating, 62 reviews

Cozy home 8 miles from OCMD *Beach Pass Included*

When is the best time to visit Ocean Pines?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price€ 144€ 142€ 137€ 154€ 173€ 202€ 235€ 232€ 184€ 168€ 149€ 153
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.

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 € 43 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    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

  • Wifi availability

    320 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!

Destinations to explore

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  3. Maryland
  4. Worcester County
  5. Ocean Pines