Holiday rentals with a fireplace in Ocean Pines

4.99 out of 5 average rating, 132 reviews

A vibrant neon sign reading 'Sea Glass Sunrise' is framed by lush green foliage, set against a backdrop of a serene beach at dawn. The soft pastel colors of the sky create a peaceful atmosphere, enhancing the welcoming ambiance of the space.

Apartment in Ocean City

Gorgeous Beachfront! King Bed, Direct Ocean View!

Stunning beachfront condo with direct view of the ocean! Your vacation home away from home! Everything you need right ON the beach. All linens, supplies and a well-stocked kitchen! New 65" TV w/free 4K Netflix provided! Modern serene decor in the heart of OC! Feel like getting out? Enjoy walking distance to Seacrets, Mackey's, and Fager's Island, Subway, Candy Kitchen or Dumsers' Dairyland! More adventure? Walk to minigolf, pontoon boats and jetski rentals! Only 4 minute drive to the boardwalk!!

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.

4.98 out of 5 average rating, 46 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

4.97 out of 5 average rating, 217 reviews

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

Ocean Pines Yacht Club Getaway Waterview

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 cozy living area features a light gray sofa adorned with decorative pillows and a small blue ottoman. Natural light brightens the space, showcasing art on the walls and a dining area in the background, complemented by a wooden table and chairs.

4.87 out of 5 average rating, 102 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.

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.

4.98 out of 5 average rating, 143 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, 126 reviews

A modern living room features a comfortable sectional sofa in neutral tones, paired with a rustic wooden coffee table. A television is mounted above a stone accent wall. Glass doors open to a balcony, allowing natural light to fill the space.

Apartment in Ocean City

Breezy Point #305 - Rooftop Deck Panoramic Sunsets

Welcome to Your Bayside Escape at Breezy Point! Step into style at this sleek bayside condo where modern comfort meets bayside views. Relax on the rooftop terrace and enjoy stunning sunset views and the fresh air. Tucked just off 28th Street, you're near restaurants, shops and quick bites. The boardwalk and beach are an easy walk or a quick drive away. A comfortable and convenient home base for couples and families. Hosting a bigger group? Ask about our other units in the same building!

Guest suite in Ocean Pines

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.

4.99 out of 5 average rating, 137 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.

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.

5 out of 5 average rating, 14 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.

4.98 out of 5 average rating, 102 reviews

The backyard features a well-maintained putting green, with white flags marking the holes. A spacious home with a covered patio and landscaped garden is visible in the background, surrounded by lush greenery and trees.

Home in Berlin

Assateague, Golf, Ocean City, all Within Minutes!

Worcester Co. Lic. #859 PLEASE NOTE: number of allowed guests: No more than 8 golfers. (Min age 25) No more than 10 adults. (Min age 25) Related families up to 12 guests. We do NOT rent to high school senior groups. Please note, we own the white house next to our STR. Occasionally you may see us there, however, we are committed to your comfort & privacy. Located 1.5 miles from Assateague Island beaches. 3 courses within .5 miles. Towels and linens for every guest.

5 out of 5 average rating, 238 reviews

A charming cottage facade is framed by white columns and features a gabled roof. Two black rocking chairs, adorned with pillows, sit on a brick porch surrounded by colorful potted flowers. Lush greenery enhances the inviting atmosphere.

Cottage in Frankford

Hobbs & Rose | A Peaceful Cottage Escape

Built in 1941 from historic “clinker bricks,” this restored cottage is a dreamy place to slow down and reconnect. Surrounded by enchanted gardens and close to the beach, Hobbs & Rose is filled with charm—gorgeous living spaces, a carved marble soaking tub, and thoughtful details throughout. Enjoy a romantic getaway and unwind in our Sanctuary meditation room, where birdsong and forest friends welcome you. You relax—we’ve created every detail to help you feel restored.

4.96 out of 5 average rating, 202 reviews

A charming bungalow features dark blue siding and large front windows, framed by neatly trimmed bushes. A concrete walkway leads to the front door, and a well-maintained lawn surrounds the home. The sky is partly cloudy, adding to the inviting exterior.

Home in Ocean City

Pet Friendly SFH w/ fenced yard, 2blocks to BEACH!

PET FRIENDLY with fenced in yard, 2 blocks to the beach! Summer rentals avail. Sunday - Sunday. An 8min walk to the beaches of N. Ocean City! Our home is located in a quiet neighborhood, between the beach & bay! You'll have access to a fenced backyard, full kitchen, smart TV, & WIFI. We expect guests to be courteous to neighbors. Parties & loud music are not permitted. **Not traveling with pets? Check out our ocean side condo near Northside Park!**

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, 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 rentals with a fireplace in Ocean Pines

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a fireplace

4.97 out of 5 average rating, 31 reviews

A screened-in room features a comfortable sectional sofa adorned with pillows, alongside a glass-topped table. Two high-backed chairs are positioned at a small table, with a view of a serene landscape and sunset reflected in the glass doors.

Home in Selbyville

Cozy Beach Escape Mallard Lakes Resort Amenities

A family-friendly home is nestled among trees, featuring a cozy outdoor area with a hammock and fire pit. The interior includes a spacious living room with a Smart TV and a welcoming layout that captures natural light, presenting a relaxing environment for guests.

5 out of 5 average rating, 58 reviews

Ocean Pines Fun – Arcade, Pools & Near O.C. Beach

5 out of 5 average rating, 42 reviews

Home in Ocean City

Bayside - Waterfront - Dock - Quiet Area

A spacious living area features a soft sectional sofa, positioned for cozy relaxation. A gas fireplace, framed by a white mantel, adds a warm touch. A smart TV is mounted on the wall, and a glass door leads to a dining area with natural light.

4.89 out of 5 average rating, 38 reviews

Serene OP cottage perfect for families!

Superhost

Home in Ocean City

5 out of 5 average rating, 4 reviews

Your Ideal Gateway Awaits

5 out of 5 average rating, 21 reviews

Villa Caribbean OCMD

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.

4.95 out of 5 average rating, 40 reviews

Cottage on the water

The exterior of a two-story home is shown, surrounded by lush greenery and mature trees. A wooden deck with railings is featured at the entrance, overlooking a pathway made of stones, while a large tree stands prominently beside the house.

4.86 out of 5 average rating, 21 reviews

Cozy Corner Retreat

Apartment rentals with a fireplace

A light-filled room features a cozy gray sofa and a large bean bag chair with decorative pillows. Three framed ocean-themed prints decorate the walls, contributing to a calming ambiance. Natural light streams through two white-framed windows with light blinds, illuminating the space.

4.9 out of 5 average rating, 40 reviews

Mermaid Cove

The kitchen area features a wooden countertop with a modern sink and stylish faucet. Shelves hold various glassware and dinnerware, while a spacious dining area is visible in the background, showcasing a large table surrounded by natural lighting.

5 out of 5 average rating, 35 reviews

Bayside Bungalow - Waterfront

Superhost

A scenic sunset is captured over calm waters, reflecting orange and yellow hues. Silhouetted structures border the image, with a wooden pier extending into the bay. A tranquil atmosphere is evoked by the soft colors of dusk.

4.67 out of 5 average rating, 94 reviews

Oasis On The Bay Amazing Bayviews. Amazing sunset.

5 out of 5 average rating, 25 reviews

A sunroom offers expansive views of a creek, showcasing sliding glass doors that allow natural light. Comfortable seating with orange cushions is arranged around a small table. A ceiling fan hangs above, and a television is mounted on the wall, creating a welcoming space.

Flat in Selbyville

Creek Suite

The spacious living room is furnished with a large sectional sofa and a smaller couch, providing ample seating. A wooden coffee table sits centrally on a light area rug. Natural light fills the room through sliding doors, leading to the dining area visible in the background.

4.94 out of 5 average rating, 89 reviews

Jada Oceanside with pool walking distance to beech

5 out of 5 average rating, 11 reviews

A dining area features a black wooden table surrounded by eight chairs, set against cheerful yellow walls adorned with framed coastal artwork. A cozy living space includes a light blue sofa and additional seating, complemented by large windows allowing natural light to fill the room.

Flat in Selbyville

Luxurious Bayville Shores Home Close to the Beach!

A serene bedroom offers a king-sized bed adorned with soft bedding, complemented by a sea-themed color palette. A large window provides expansive ocean views, while natural light fills the space. A flat-screen TV is mounted on the wall, and light drapes frame the window.

4.97 out of 5 average rating, 33 reviews

Oceanfront Oasis | Indoor Pool | Hot Tub | Deck

The exterior of the Beach Winds condo building is shown, featuring three levels with several balconies, white railings, and an overhang. The structure is painted in soft green and beige tones, with stairs ascending to each floor, framed by neatly landscaped greenery.

4.85 out of 5 average rating, 247 reviews

Ocean view 2 Bed 2 bath CLEAN!

Villa rentals with a fireplace

The exterior of a spacious home is surrounded by greenery, featuring large windows that invite natural light. A gravel driveway leads to the entrance, which is accented with steps and a circular front window.

Villa in Ocean Pines

4.43 out of 5 average rating, 72 reviews

Luxe Homey Get-Away Beach Cove

New place to stay

Bear Trap. First-Floor, Pet-Friendly & Pond Views

The living room offers comfortable seating with two upholstered chairs and a sectional sofa. A glass coffee table is centered on a plush carpet, while a gas fireplace and Smart TV are positioned on the wall. Natural light is welcomed through large front windows.

4.82 out of 5 average rating, 45 reviews

4 Mi to Bethany Beach: Sunny Escape w/ Porches!

The exterior of the condo unit is shown, featuring a covered deck and a screened porch. Green grass surrounds the building, while neatly trimmed hedges add to the landscaping. Steps lead up to the entrance, and the structure is painted in light tones with multiple windows.

4.9 out of 5 average rating, 155 reviews

Modern 3 BR 1st floor resort villa, near beach

4.99 out of 5 average rating, 92 reviews

Villa in Ocean City

Walk to the Beach! Fire Pit-Fenced Yard-N64-Bikes!

A comfortable living room is highlighted by a spacious gray sectional sofa and a circular wooden coffee table. A flat-screen TV is mounted above a modern fireplace, while large windows allow natural light to illuminate the space. A colorful area rug adds a cozy touch.

Villa in Millville

5 out of 5 average rating, 7 reviews

Screened Porch, Outdoor Shower: Millville Villa

Two adirondack chairs are positioned on a balcony, facing a golf course with lush green grass and a serene lake. A small table holds two cocktails, complemented by the backdrop of trees and a clear sky.

Villa in Ocean Pines

5 out of 5 average rating, 4 reviews

Lakeview/Golf course front home - 4 Bed/3 baths

The exterior of the villa is shown, featuring a modern design with a combination of stone and painted siding. The first-floor unit is highlighted, showcasing a private entrance and a small patio area. Large windows offer a view of the well-kept landscaping.