House holiday rentals in Ocean Pines

The front exterior of the house features a yellow facade with large windows and a welcoming doorway. A wooden deck is accessed by a set of stairs, and outdoor chairs are positioned for seating. Surrounding trees indicate a natural, wooded setting.

4.95 out of 5 average rating, 39 reviews

Salty Serenity

Relax and recharge at our cozy 3 bed/2 bath home in Ocean Pines, a peaceful community near Ocean City, MD. Enjoy bikes, kayaks, and a fire pit in the large backyard, or use the pools, marina, yacht club, and golf course in the neighborhood. Beach parking at the Ocean Pines Beach Club in Ocean City is included. You can explore the boardwalk, casino, outlets, and the many nearby restaurants. Or, visit Berlin, or see the wild horses at Assateague Island. Come experience all the area has to offer!

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, 98 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, 137 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 spacious living area is furnished with two dark leather sofas, providing ample seating. A ceiling fan enhances airflow. The open layout connects to a dining area featuring wooden chairs, while the kitchen is visible in the background, showcasing modern appliances and cabinetry.

4.94 out of 5 average rating, 227 reviews

Right behind Alley Oops & Crab Bag. Walk to beach

Look no further! With Alley OOps in the backyard and a 5-minute walk to the beach, pool, tennis, and shopping, the fun is endless. This 3 bedroom, 2 bathroom house has high-end furniture, fast wifi, 4 flat screens and 2 free parking spots with street parking when available. Our Community offers all of these amenities included in your rental and free putt-putt too! Enjoy our natural wood-burning fireplace and large porch to take in the sunset through the trees. We do not rent to under 25.

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, 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.

A spacious living room features a comfortable dark sofa, two brown chairs, and a cozy fireplace. Natural light enters through large windows adorned with light blue drapes. A ceiling fan and recessed lighting contribute to a bright and airy atmosphere, complemented by modern decor.

4.99 out of 5 average rating, 110 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 vibrant living area is highlighted by tropical-patterned wallpaper and warm wooden flooring. Comfortable seating is arranged around a central coffee table, complemented by an accent table in the corner. A large mirror reflects the space, adding depth and light.

4.83 out of 5 average rating, 41 reviews

Cottage in the Pines

The mid-century modern house sleeps 6 with 3 bedrooms and 1 ½ baths. There is a peaceful back porch, parking for 3 cars, laundry, and wifi. Ocean Pines has community pools, tennis and pickleball courts, a golf course, yacht club, and playgrounds. It’s a great place for fishing, boating, kayaking, biking and hiking, and just a 10-minute drive to the boardwalk or a 20-minute drive to Assateague Island National Seashore. Guests can access Ocean Pines pools and beach club for a fee.

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, 12 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.

A barn-style exterior of the condo is showcased, featuring a metal roof and three large garage doors at ground level. The second floor includes a deck with an entrance door. Expansive green space surrounds the property, with trees visible in the background under a clear blue sky.

4.95 out of 5 average rating, 80 reviews

SpaciousCondo nearOcean City|Winery|Golf on 5Acres

Come stay in our 2nd Floor Condo on our private 5-Acre Property! Enjoy the Barn-Like look from the outside, but inside, find a modern & spacious condo with a fully-equipped kitchen. Located in Berlin, Maryland, you are minutes to Historic Berlin and only 15 minutes to all the fun that Ocean City, Maryland has to offer! Have your morning coffee on the deck and soak in the scenic views or pitch a tent, light up the fire pit, let the kids run wild! We'll see you soon!

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.

4.85 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*

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.

Superhost

A cozy living area features a leather armchair positioned next to a small side table with a lamp. A storage chest rests on the floor beneath a collection of framed artworks and a flat-screen television, enhancing the eclectic atmosphere of the space.

4.82 out of 5 average rating, 140 reviews

Joy in the Morning @ Berlin Boho Bungalow

The Berlin Boho Bungalow is the dream home of a family of artists—a mother and daughter team, a contractor husband, and adult grandkids. Set on 1.5 acres in historic Berlin, MD. There are two units in the house. This is the downstairs guest house. We invite you to start family traditions here and return year after year. As we lovingly restore this old farmhouse, you can celebrate the transformation of a once-abandoned home into something beautiful.

Popular amenities for house rentals in Ocean Pines

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The living room features two plush sofas and two accent chairs, arranged around a circular coffee table. A flat-screen TV is mounted above a gas fireplace, and large windows allow natural light to fill the space, showcasing views of the bay.

4.96 out of 5 average rating, 23 reviews

Beach Paradise 2101-Downtown Luxury Condo Bay View

5 out of 5 average rating, 106 reviews

The exterior of the single-family home is shown, featuring a welcoming entrance with a striped awning. A well-maintained front yard with shrubs and a tree provides shade, while the attached garage is visible on the left.

Home in Frankford

Quiet 3BR Coastal Home Minutes to Bethany Beach

5 out of 5 average rating, 58 reviews

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

Superhost

A cozy living area is presented with a neutral color palette, featuring a comfortable gray sofa, two matching chairs, and a wooden coffee table. Natural light fills the space through sliding glass doors, which offer access to an outdoor deck, while a framed artwork enhances the decor.

4.89 out of 5 average rating, 18 reviews

Bayside Townhome with Ample Parking

A wooden pier extends into calm waters, framed by posts topped with white caps. A vibrant sunset bathes the scene in warm hues of orange and yellow, reflecting beautifully on the water's surface. The distant silhouette of trees and community is visible against the dramatic sky.

4.81 out of 5 average rating, 212 reviews

Bayside community near OCMD great rates

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, 138 reviews

Little house in Berlin, Md.

4.9 out of 5 average rating, 40 reviews

The living room features ample seating on a sectional couch, complemented by an area rug and coffee table. Natural light streams through large windows, illuminating the space. A TV and sound bar are mounted on the wall, enhancing the entertainment options.

Home in Ocean View

Boho Beach Golf Villa- 2026 booking fast!

A welcoming approach to a spacious home is depicted, framed by tall trees reaching towards a bright blue sky. A neatly paved driveway guides the eye towards the house, with manicured lawns and colorful foliage adding to the inviting landscape.

4.97 out of 5 average rating, 69 reviews

Coastal Oasis in Ocean Pines

Weekly house rentals

A dining area displays a wooden table set for six, featuring white plates, silver cutlery, and sparkling glasses. A vibrant centerpiece of sunflowers and decorative pumpkins is placed on a bright red runner. The adjoining kitchen is visible, showcasing modern cabinetry.

4.97 out of 5 average rating, 64 reviews

Summer By The Sea

Superhost

4.5 out of 5 average rating, 4 reviews

Bayfront on Brighton~Waterfont~No Pet Fee

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.

5 out of 5 average rating, 21 reviews

Waterfront Vacation Home in Ocean Pines

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, 37 reviews

Serene OP cottage perfect for families!

A single-story house is positioned among tall trees, showcasing a welcoming front porch with steps leading to a paved driveway. Surrounding landscaping includes trimmed bushes and grassy areas, creating a natural setting that fosters a sense of privacy.

4.95 out of 5 average rating, 38 reviews

Beachin' it in Ocean Pines

Colorful armchairs with a fish pattern provide comfortable seating by large windows that offer views of the water and surrounding nature. A small green side table stands between the chairs, adorned with a vase of flowers.

4.8 out of 5 average rating, 46 reviews

The Oliver House

4.95 out of 5 average rating, 21 reviews

White Marlin Cottage>HOT TUB<

A spacious living area features a wood-paneled ceiling and large windows, providing a sweeping view of the St. Martin River. Comfortable seating arrangements include dark sofas and a wooden dining table, complemented by natural light flowing into the room.

5 out of 5 average rating, 20 reviews

Villa Caribbean OCMD

Private house rentals

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.

4.95 out of 5 average rating, 56 reviews

Coastal Retreat: River View & Pine Haven

A bright living area features a comfortable blue sofa and an armchair, with a decorative lamp beside them. A white coffee table sits atop a patterned rug, which complements the room's light decor. Two windows, adorned with blinds, allow natural light to filter in.

5 out of 5 average rating, 18 reviews

Stubbe's Beach House, Home in Ocean Pines, MD

4.93 out of 5 average rating, 14 reviews

Peace in the Pines- 3BD, 2BA w/ Beach Club Pass

The A-frame cottage features large front windows, allowing natural light to fill the interior. Wooden siding blends harmoniously with the surrounding trees. A spacious deck is accessible, adorned with outdoor seating. Dappled sunlight casts shadows on the ground, creating a serene outdoor setting.

4.88 out of 5 average rating, 34 reviews

Captivating A-Frame in beautiful, Ocean Pines

A modern kitchen showcases a spacious island with seating for four. Elegant cabinetry and stainless-steel appliances complete the design. Natural light floods the area, highlighting the marble countertop and the decorative accessories. A large TV is mounted on the wall for convenience.

5 out of 5 average rating, 50 reviews

New waterfront home on bay, quick walk to beach

An open living area is presented, featuring a spacious sectional sofa, a light wood dining table with seating for six, and a modern kitchen. Natural light floods the space through large windows, enhancing the neutral color palette and warm wood accents.

5 out of 5 average rating, 17 reviews

House with Fire Pit + Private Yard near Ocean City

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, 66 reviews

Ocean Pines, Waterfront Oasis

A large, multi-story beach mansion is showcased in the early evening light. The exterior features a mix of blue siding and white trim. Lush greenery and colorful plants surround the entrance, while multiple balconies are visible on the upper levels.