House vacation 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 modern dining area features a rectangular table surrounded by six upholstered chairs. Large windows allow natural light to fill the space, with views of the surrounding trees. A stylish light fixture hangs above the table, and a door leads to the outdoor deck.

5 out of 5 average rating, 70 reviews

OC Gateway: Modern 4BR/2.5BA home (dog friendly)

Have fun with the whole family at our stylish Ocean City-convenient home! This wooded beach house boasts many modern upgrades including a beautiful kitchen with gas range, large flat panel televisions in almost every room, a washer and dryer, and even a Wii video game system in the living room! Queens in 3 bedrooms and a bunk bed with trundle in the 4th! Finally, enjoy all the amenities of Ocean Pines including access to 5 pools, a private OC beach club (w/pool!), and much more! Lic. No. 4586.

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 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.

A charming cottage exterior is showcased, featuring a distinctive A-frame design. The front porch is framed by wooden railings, while a path of stepping stones leads to the entrance. Surrounding trees provide a natural backdrop, enhancing the serene outdoor environment.

5 out of 5 average rating, 23 reviews

Ocean Pines 2BR 1BA Cottage with Fire Pit

Pint-sized, pet friendly cottage close to everything, the perfect, quiet little sanctuary. Full kitchen in case you wish to cook in one night. Dining table and a cozy living room. Board games, yard games, pickle ball equipment, outdoor seating, fire pit and a grill round out this amazing cottage. Accommodates 6 people, recommend no more than 4 adults. Close to the Woodlands Restaurant & the Pines Public House. Not far from the Ocean Pines Sports Core Pool and the Ocean Pines Golf Club.

A living area showcases a comfortable layout with two dark sofas, accent pillows, and a wooden coffee table. A large area rug features a blend of soft blue hues. The space is warmly lit, with a dining area visible in the background and cabinetry seen in the kitchen.

4.92 out of 5 average rating, 25 reviews

Offshore Tails

You and your pets (up to 4, no breed/size restriction) can forget your worries in this serene home with spacious bedrooms. A fenced yard awaits your furry friends, open floor plan and only 10 minutes from OC in the Ocean Pines Community. Ocean Pines offers many amenities such as indoor and outdoor pools, 2 restaurants, indoor and outdoor sports courts, boat and kayak launches, skate parks to just name a few! This rental includes the OP Beach Club Parking pass in Ocean City for guest use.

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 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*

4.85 out of 5 average rating, 198 reviews

The cottage exterior is seen with a large deck featuring white railings and a blue and white striped awning. A set of outdoor furniture is arranged on the deck, and steps lead down to a grassy area. The well-maintained, light-colored siding complements the serene environment.

Home in Fenwick Island

Hall Cottage, Fenwick Island, Delaware

Charming, updated cottage. Wifi and space to work. Located between Bethany Beach, DE and Ocean City, MD, Fenwick is known as 'The Quiet Resort.' Two blocks to the beach. The cottage is the perfect size for a couple or small family. Sitting on a lovely, quiet block, between the ocean and the bay, the cottage is a quick walk to fine dining, pubs and shopping. The cottage comes with two beach chairs and an umbrella, an outdoor shower, and a beach parking pass.

Popular amenities for Ocean Pines house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A light and airy deck features a rectangular dining table surrounded by aqua-colored chairs. A calm water view is visible beyond the railing, with flags gently waving in the breeze. Soft lighting is provided by string lights overhead, enhancing the inviting atmosphere.

4.94 out of 5 average rating, 275 reviews

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

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

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

4.81 out of 5 average rating, 212 reviews

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.

Home in Berlin

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

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

Superhost

4.89 out of 5 average rating, 38 reviews

Cozy Stay by the Bay

4.88 out of 5 average rating, 144 reviews

Beautiful Cottage W/ shared pool & close 2 beach

Weekly house rentals

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

Superhost

4.5 out of 5 average rating, 4 reviews

Bayfront on Brighton~Waterfont~No Pet Fee

4.95 out of 5 average rating, 80 reviews

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.

Home in Berlin

SpaciousCondo nearOcean City|Winery|Golf on 5Acres

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

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 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

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

Private house rentals

5 out of 5 average rating, 44 reviews

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.

Home in Berlin

Cozy, Private Beach home

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

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, 11 reviews

Perfect Golf Group - 4BR 3BA on Golf Course

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!

The open-concept living room features two dark sofas adorned with decorative pillows, centered around a round coffee table. Bright overhead lighting illuminates the space, which leads into a modern kitchen visible in the background, creating a welcoming and functional gathering area.

4.98 out of 5 average rating, 59 reviews

Cozy home 8 miles from Ocean City, MD

A bright living area features a cozy sectional sofa and an electric fireplace beneath a contemporary entertainment center. Large windows allow natural light to fill the space, while a dining table for six is visible in the background, complemented by colorful window treatments.