House vacation rentals in Ocean Pines

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.

4.97 out of 5 average rating, 36 reviews

WHAT DAY IS IT???????

ENJOY YOUR VACATION WITH A NICE VIEW OF THE QUIET CANAL! THIS SPACIOUS 4 BEDRM/2.5 BATH SMOKE-FREE PROPERTY IS LOCATED IN OCEAN PINES WHERE YOU AND THE FAMILY CAN ENJOY 5 POOLS(w/ fee), THE BEACH, YACHT CLUB, TENNIS AND GOLFING. WE'RE JUST A SHORT DRIVE FROM OCEAN DOWNS CASINO, GO-CARTS, THE BOARDWALK, WATER PARKS, ASSATEAGUE ISLAND & MORE. THE SUNROOM LEADS TO A LARGE DECK WITH GRILL & FIRE PIT. OUR KITCHEN IS LOADED W/ ALL THE NECESSITIES. 2 OF THE BEDROOMS ARE LOCATED ON THE FIRST FLOOR.

A welcoming covered porch features comfortable seating arrangements, including a swing and cozy chairs. Lush plants are placed in yellow pots, adding greenery to the space. A chandelier is visible above, enhancing the inviting atmosphere of this shaded outdoor area.

4.86 out of 5 average rating, 91 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.

A pair of teal Adirondack chairs sits on a wooden dock overlooking calm water. Decorative pillows add a touch of comfort. Boat slips are visible in the background, with a soft reflection on the water's surface as the sun sets behind scattered clouds.

4.94 out of 5 average rating, 34 reviews

Cottage on the water

We are located right off of Route 90 and minutes to the beach. Ocean Pines is filled with amenities. We have a public access yacht club and golf course are close to the town of Berlin for dining and a visit to the famous Burley Oak Brewery. The family will enjoy Ocean City for fun at Jolly Rogers or the Boardwalk for the rides. West Ocean city has the famous Orange Crush at the Harborside restaurant and don't forget Assateague Island and the horses. We are also 2 miles from the local winery.

A gathering area features multiple wooden adirondack chairs arranged around a circular fire pit. The scenic view includes a calm body of water with boats docked nearby and houses lining the shore under a clear blue sky.

4.98 out of 5 average rating, 126 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!

A two-story blue house is framed by trees, with a well-maintained front yard. The home features black shutters and white steps leading to a central door. A porch flag and a welcoming bench are visible, enhancing the inviting exterior.

4.96 out of 5 average rating, 136 reviews

Little house in Berlin, Md.

Our home is located in Ocean Pines, Maryland. Spend the day at the beach, golf, come back and relax on our spacious screened porch. The community has 5 pools, walking trails, Parks, and more. The house is a short drive to Ocean City, Md. (8 Miles) via Rt. 90 or Rt. 50. Assateague Island National Seashore is also just a short drive 12 miles. You can see wild horses, beautiful sunsets, ride bikes, or go to the beach. There are many golf courses within 15 miles of the house all very nice.

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.

4.96 out of 5 average rating, 113 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.

The exterior of the rancher is shown, featuring a light gray facade with a welcoming porch and a decorative railing. A pathway leads to the entrance, surrounded by a manicured lawn and small shrubs. An American flag is displayed prominently on the right side.

4.98 out of 5 average rating, 89 reviews

Cozy home on quiet court; 10 mins from Ocean City

Beautiful, comfortable rancher on a quiet cul-de-sac, perfect for families and adults looking for a quiet, relaxing stay. We offer 3 bedrooms and 2 bathrooms on one level, located in the north side of the Ocean Pines community. We have a large driveway, and a combo screened in / open air deck for outside relaxation. Ocean Pines is a 10 minute drive to Ocean City and boasts over a dozen parks and walking trails, a public Yacht Club, 5 pools, 2 marinas, and a championship golf course.

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.

4.91 out of 5 average rating, 185 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!

Superhost

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.

5 out of 5 average rating, 63 reviews

Ocean Pines, Waterfront Oasis

"Endless Summer" is on the canal at Moonshell Dr. Located on the St Martins River, North of the Rt 90 bridge in Ocean Pines. Centrally located, close to downtown Ocean City, MD, "the boardwalk", bustling West OC and historic Berlin, MD. Explore Assateauge Island, Del. beaches all minutes' drive in the amenity filled [pools, golf, pickle ball, tennis, trails and parks] OP community. Linens, cleaning team and beach club parking included. Must be 25 or older or military service.

Superhost

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.

4.84 out of 5 average rating, 131 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*

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.

4.97 out of 5 average rating, 102 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.

A bright living area features a comfortable blue sofa and a cozy armchair, with a gas fireplace as the focal point. Natural light floods the space through large windows, while a dining table and chairs are visible in the background, creating an inviting atmosphere for gatherings.