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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, 192 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! 🏖️💞☀️

Guest favourite
The exterior of the waterfront home is shown, with a spacious deck and screened porch overlooking the water. Lush landscaping and a pathway lead to the dock, while large windows create a welcoming atmosphere. A patio umbrella provides shade for outdoor seating.
Home in Ocean Pines
5 out of 5 average rating, 66 reviews

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.

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, 43 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
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, 398 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 modern dining area features a rectangular table surrounded by six upholstered chairs. Large windows allow natural light to fill the space, with views of the surrounding trees. A stylish light fixture hangs above the table, and a door leads to the outdoor deck.
Home in Ocean Pines
5 out of 5 average rating, 76 reviews

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

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, 140 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!

Guest favourite
Home in Ocean Pines
5 out of 5 average rating, 6 reviews

Waterfront Home-Turnville Creek

Nestled on turnville Creek, this 4 bedroom, 2.5 bath, pet-friendly waterfront home is the perfect place for multiple families to vacation in Ocean City. Waterfront views, spacious yard, and 10 minutes from ocean city situated behind the ocean downs casino on turnville creek. Bring your boat or a rent a boat and dock it here - there is a boat ramp a half mile down the road in our neighborhood. We hope to accommodate you and provide an experience that is becoming increasingly unique to find.

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.

Top guest favourite
A charming house with a light blue exterior is surrounded by lush greenery. A spacious deck features potted plants and outdoor seating. Colorful Adirondack chairs in red and blue are placed around a small fire pit on a patterned stone patio, inviting relaxation.
Home in Ocean Pines
5 out of 5 average rating, 13 reviews

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.

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*

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

Top guest favourite
Cottage in Ocean Pines
4.97 out of 5 average rating, 33 reviews

Cozy Cottage near the Ocean and Wild Horses

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
Home in Ocean Pines
4.85 out of 5 average rating, 52 reviews

Amazing and peaceful family fun 4 bedroom home

Top guest favourite
A welcoming entryway features a white door with a decorative window. Light wood flooring extends into a spacious living area, complemented by soft beige walls. A ceiling fan hangs above, while a table lamp illuminates a seating area. A glimpse of a well-equipped kitchen is visible in the background.
Flat in Ocean Pines
5 out of 5 average rating, 51 reviews

Be our guest

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
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

Superhost
A circular wooden deck overlooks tranquil waterfront views, featuring a mix of green grass and trees. Comfortable seating is positioned on the deck, allowing for relaxation while enjoying the serene surroundings. A two-story home and docks are visible in the background.
Home in Ocean Pines
4.79 out of 5 average rating, 14 reviews

Oceans End Waterfront Retreat

Guest favourite
A large outdoor swimming pool is surrounded by a paved deck equipped with numerous lounge chairs for relaxation. Lush greenery frames the area, and a few trees provide a touch of shade. A white building is visible nearby, adding to the inviting atmosphere.
Home in Ocean Pines
4.88 out of 5 average rating, 41 reviews

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

When is the best time to visit Ocean Pines?

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Avg. price£132£124£127£133£150£175£203£200£159£145£128£132
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 £37 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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