House holiday rentals in Ocean Pines

4.95 out of 5 average rating, 41 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

A spacious living area features two sofas, one in dark leather and the other in a light fabric, arranged around a low wooden coffee table. A flat-screen TV is mounted on a light wall above a stone fireplace, adding a cozy touch to the room.

4.97 out of 5 average rating, 133 reviews

Cozy 3 BR Pet Friendly Beach, Bay & Pond nearby.

Relax with the family in this comfortable and charming home. There is room for 8 to sleep comfortably. The dining room and breakfast nook offer plenty of seating for all with a spacious kitchen. Our corner lot offers the option for outdoor fun like slip and slide, corn hole, frisbee, and more! Nearby: Beach, Bay, Wildlife sanctuary surrounded by a walking trail, Pool, Tennis, restaurants & Eventful Northside Park! Quiet and peaceful location to make family or romantic memories of a lifetime.

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, 136 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, 138 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.

4.86 out of 5 average rating, 113 reviews

A modern kitchen is showcased with a dark refrigerator and sleek stainless steel appliances. A central island features a light granite countertop, while decorative shelves display dishware against a vibrant blue wall. Pendant lights illuminate the area, enhancing the functional layout.

Home in Ocean View

Pet Friendly | New EV Charger - New 100’ Fence!

NEW Fence JUST INSTALLED! 7 Hudson is a COMPLETELY renovated, three-bedroom, two full bathroom / family & pet friendly cottage that has everything you need for the perfect getaway. With 55” TV’s in every room. Located less than one mile to the town of Bethany Beach and within walking distance to restaurants, walking trails, parks, and other attractions. There are no CO producing appliances. Hardwired CO monitors on both floors. Thank you for your interest. (King bedroom on 1st & 2nd floor)

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.

The exterior of a two-story house is framed by lush greenery and neatly arranged flower beds. A covered front porch with white railings invites guests, while the clean lawn extends towards the street. The sky above showcases a mix of clouds and blue.

5 out of 5 average rating, 115 reviews

Stay Salty OC Beach House

Welcome to your ultimate getaway near Assateague State Park & Ocean City! Our spacious retreat sleeps 14 guests and boasts resort-style amenities including pools, a gym, kayaks, and tennis courts. Located just moments from beaches, charming towns, and exciting attractions, you'll have everything you need for an unforgettable vacation. With a fully stocked kitchen, game rooms, cozy reading nooks, puzzles, and a balcony, there's something for everyone. Book now and let the relaxation begin!

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, 102 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.

4.85 out of 5 average rating, 40 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 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, 136 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.

Popular amenities for house rentals in Ocean Pines

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

An aerial view of a spacious waterfront property showcases a well-manicured yard with a private boat dock. The surrounding neighborhood is visible, featuring a variety of homes, some with outdoor amenities like pools and decks. The serene bay can be seen in the background.

4.79 out of 5 average rating, 14 reviews

Waterfront Home with views of OC Skyline!

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.

4.94 out of 5 average rating, 36 reviews

Salty Serenity

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, 57 reviews

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

The kitchen area showcases wooden cabinetry and a central island, with essential appliances visible. A round dining table with wooden chairs is positioned nearby. Natural light is introduced through a window, creating a bright and functional cooking space.

4.81 out of 5 average rating, 212 reviews

Bayside community, near OCMD, great rates

A modern two-story home is situated on a tree-lined lot, featuring a welcoming front entrance. Brightly colored adirondack chairs provide seating in the gravel area by the driveway, which accommodates several vehicles. Natural light filters through the trees, creating a serene environment.

4.95 out of 5 average rating, 42 reviews

Beautiful Spacious 4 Bedroom Home in Ocean Pines

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

4.88 out of 5 average rating, 142 reviews

Beautiful Cottage W/ shared pool & close 2 beach

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, 43 reviews

Tranquil Waters, OceanPines, 3 br, Dog Friendly

Weekly house rentals

4.96 out of 5 average rating, 27 reviews

An elevated beach house stands gracefully by the canal, with a spacious upper deck visible under a colorful twilight sky. Lush trees frame the property, while a wooden dock provides direct access to the water, creating a serene and inviting coastal atmosphere.

Home in Ocean View

Cozy Stylish Waterfront 3BR Kayaks Fireplace Porch

The living area features a mix of modern and cozy elements. A gray sofa and armchair are positioned around a wood coffee table. A large TV is mounted on the wall, and natural light streams through the nearby window. Decorative plants and a staircase with palm motifs enhance the space.

5 out of 5 average rating, 43 reviews

Cozy, Private Beach home

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 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

The expansive view showcases the sandy beach stretching along the Atlantic Ocean, gently reflecting the clouds above. Features include a shared pool bordered by lounge chairs and landscaped areas. The setting sun casts warm hues over the water, enhancing the serene coastal atmosphere.

4.79 out of 5 average rating, 14 reviews

Oceanfront | Beachfront | Elevator | eFireplace

5 out of 5 average rating, 84 reviews

A well-maintained house features a light-colored exterior surrounded by landscaped flower beds. A gravel driveway leads to the entrance, which is adorned with potted plants. Lush greenery and a distant building are visible in the background beneath a partly cloudy sky.

Home in Selbyville

Lighthouse Cottage- Pet Friendly & Close to beach

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

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, 19 reviews

Villa Caribbean OCMD

Private house rentals

5 out of 5 average rating, 21 reviews

The coastal beach home is showcased under a bright blue sky. Two colorful paddleboards are positioned upright against the house, while a gravel driveway leads to the ground-level entry. Verdant foliage provides a natural backdrop, enhancing the inviting outdoor space.

Home in Bethany Beach

Ocean Dreamin'

A comfortable living room features a light-colored sectional sofa adorned with blue and patterned cushions. A coffee table displays decorative items, and a side table holds a lamp. Natural light is filtered through sheer curtains, illuminating artwork on the walls and indoor plants.

4.88 out of 5 average rating, 8 reviews

Spacious seashore getaway.

An airy living space is highlighted by a high ceiling and large windows, inviting natural light. A gray sectional sofa faces a stone fireplace and a mounted television. Light blue cabinetry marks the kitchen area, with a dining table positioned nearby for flexibility.

5 out of 5 average rating, 10 reviews

Perfect Golf Group - 4BR 3BA on Golf Course

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, 38 reviews

WHAT DAY IS IT???????

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, 74 reviews

SpaciousCondo nearOcean City|Winery|Golf on 5Acres

5 out of 5 average rating, 54 reviews

A cozy family room is presented with a large flat-screen TV mounted above a stone fireplace, featuring comfortable seating options, including a spacious sofa and a futon. Vibrant arcade games are visible against the textured wall, enhancing the entertainment options.

Home in Bethany Beach

Coastal Cottage! Walk to Beach!

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, 45 reviews

The Oliver House

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.