Vacation rentals with a fireplace in Ocean Pines

The entrance to the A-frame home features a well-maintained wooden deck, flanked by blooming flowers in planters. The door is painted in a welcoming shade of coral, and large windows allow natural light to illuminate the entryway.

5 out of 5 average rating, 49 reviews

hi-A-tus A-frame

Charming A-frame nestled in the heart of Ocean Pines. Open floor plan, softest sheets, flat screen TVs, high speed WiFi, in an amenity filled community surrounded by multiple beaches. 10 min from Ocean City and 15 min from Assateague! Sleeps 4 comfortably. Perfect for 4 adults or family. Must be 25 yrs old. Enjoy all that Ocean Pines has to offer including 5 pools, multiple playgrounds, yacht club and farmers market. Weekly rental during the high season. Please inquire about longer stays.

An inviting main living area features a spacious sectional sofa arranged for comfort and conversation, alongside a cozy fireplace. The room showcases vaulted wood ceilings and a tasteful blue accent wall, with a flat-screen TV mounted for entertainment and large windows allowing natural light to fill the space.

4.93 out of 5 average rating, 28 reviews

Ocean Pines Chalet

Nestled in the tranquil Ocean Pines, MD, Ocean Pines Chalet is a picturesque 4-bedroom, 3.5-bath haven exuding coastal charm. This delightful retreat is surrounded by a plethora of local amenities including community pools, parks, tennis and basketball courts, skate parks, golf, and a yacht club. A 15-minute drive from the bustling Ocean City beaches, it offers the perfect blend of serene living and beachside excitement, making it an ideal getaway for those seeking both relaxation and adventure

4.97 out of 5 average rating, 166 reviews

An expansive outdoor gathering area is filled with guests enjoying live music in the evening. The venue features a large multi-level building with blue roofs and surrounding greenery. The water is visible in the background, reflecting the twilight hues.

Condo in Ocean Pines

Getaway in Ocean Pines

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

A spacious bathroom features dark marble walls and a large bathtub with gold fixtures. A wide mirror reflects the bright room and various toiletries are visible on the countertop. Soft lighting creates an inviting ambiance, enhancing the functional layout.

4.85 out of 5 average rating, 84 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 rustic wooden barn door with a sliding rail is featured, adding a charming farmhouse touch. Beige walls complement the door, and a glimpse of a dining area with a wooden table and chairs is visible in the background, creating an inviting atmosphere.

4.93 out of 5 average rating, 27 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.

An aerial view captures a vibrant waterfront venue bustling with visitors enjoying an evening event. A spacious outdoor patio is highlighted, adjoined by a marina filled with boats. The setting sun casts a soft glow over the scene, while nearby trees outline the serene backdrop.

4.98 out of 5 average rating, 120 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!

4.95 out of 5 average rating, 59 reviews

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

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, >3 guests may apply.

A well-lit hallway is seen, featuring white paneled walls with a circular mirror on one side. A wall hanging displaying the word 'LOVE' adds a touch of color, while smooth flooring extends toward doorways leading to bedrooms and bathrooms.

4.83 out of 5 average rating, 59 reviews

Ocean Pines Escape

A quaint, newly renovated beach house in Ocean Pines, with three bedrooms and two baths. Full size kitchen with dining table for 6. It has a screened in deck out back with a grill. Use of parking pass for the Ocean Pines Beach Club in Ocean City, with acess to bar and concessions. Enough parking for 4-5 vehicles. Basketball hoop in driveway which is big enough for pickle ball. Games and PacMan video arcade for indoor fun. Non- smoking on property. No high school senior week guests.

4.99 out of 5 average rating, 161 reviews

A serene pathway meanders through a lush garden, bordered by tall trees and vibrant foliage. Stacked stones and gravel create a natural walkway, leading to serene ponds and landscaped areas. A wrought-iron bench sits nearby, inviting quiet moments in nature.

Cottage in Frankford

19th Century Coastal Cottage with Modern Amenities

Built from “clinker bricks” in 1941 to house poultry feed, this Airbnb is a dreamy place to slow down. Exposed wood beams and interior brick walls as well as all the luxuries required for a rural escape. This charming cottage near the beach & is surrounded by enchanted gardens. You will swoon over the carved marble bathtub and gorgeous living areas. Perfect for a romantic getaway, Hobbs and Rose Cottage is waiting to create a memorable experience for you! NEW for 2025, our mediation room!

Guest suite in Ocean Pines

A charming small-town street features a variety of storefronts with decorative signs and awnings. Potted plants adorn the sidewalks, and lampposts line the pathway. A few pedestrians stroll leisurely, conveying a peaceful and inviting atmosphere.

4.99 out of 5 average rating, 120 reviews

Newly built bright and airy guest suite!!!!

Welcome to our new 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 breathtaking waterfront Yacht Club with restaurant and live music (seasonal), Robert Trent Jones Sr. golf, farm market, playgrounds, 5 pools/fee (4 seasonal), and racquet club.

A spacious living area is highlighted by large windows allowing natural light to fill the room. Comfortable seating includes a sectional sofa and two armchairs. A coffee table sits in the center, while decorative elements and a fireplace add a cozy touch.

4.99 out of 5 average rating, 86 reviews

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!

A sandy beach view showcases gentle waves rolling in from the ocean. Grassy dunes frame the foreground, with a wooden post marking the beach entrance. A wooden fence runs parallel to the shoreline, creating a serene atmosphere for beachgoers.