Holiday rentals in Ocean Pines

4.9 out of 5 average rating, 150 reviews

Cottage in Ocean Pines

Cozy Beach Getaway in the Lovely Ocean Pines North

Welcome to our Cozy Beach Getaway!! ☀️🌊👙⛱️🐚🏖️🌞🌅⛅️ This beautiful and peaceful home is located in Ocean Pines North. 3 bedrooms, 2 bathrooms. Peaceful front porch and back deck. 🏡🏝️ Whether you’re looking for a summer family vacation, girls weekend getaway, or just a break from reality, this is the perfect place! Washer/dryer 🧺, two smart TV’s 📺, driveway fits 4 cars comfortably 🚗. Enjoy the hustling city of Ocean City during the day and stay in the tranquility and peaceful Ocean Pines at night! 🏖️💞☀️

Guest suite in Ocean Pines

4.95 out of 5 average rating, 377 reviews

Stunning private waterfront suite

Welcome to your cozy getaway with stunning water views from every room! This sweet 2-bedroom, 1-bath suite boasts a private entrance, a living room, and a cute kitchenette. Nestled in a peaceful, family-friendly neighborhood, you'll have year-round access to swimming pools, a golf course, tennis courts, a Yacht club, and lovely parks nearby. Only a quick 10-minute drive lands you on the sandy beaches and lively Boardwalk of Ocean City. Park in the driveway and step into your own private escape!

4.96 out of 5 average rating, 168 reviews

Apartment 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

4.98 out of 5 average rating, 121 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

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.

4.95 out of 5 average rating, 21 reviews

Peaceful, pet and family-friendly beach retreat

Escape the busy and hurried life in our Ocean Pines home. Nestled among the trees, enjoy your coffee peacefully, sitting on the wrap-around deck. Unwind in our open and bright family room with lots of natural light and huge windows. Equipped with fast WI-FI and lots of other essentials, we know your stay will be easy and relaxing. It's stocked with everything you need for a family vacation-games, puzzles, books, grilling supplies, kids supplies (pack-n-play, bibs, booster chair), and more!

Guest suite in Ocean Pines

4.99 out of 5 average rating, 121 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.

4.95 out of 5 average rating, 102 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.

4.96 out of 5 average rating, 28 reviews

Cottage in Ocean Pines

Cozy Cottage near the Ocean and Wild Horses

Blissfully quiet 1000 sq. feet, 3 rooms (2 bedrooms, and 1 telework-ready study), 2 full bathrooms, and screened in porch. Surrounded by towering pine trees yet only minutes from the tranquility of Assateague National Park or the excitement of the Ocean City boardwalk, "Burr Hill" has it all. Easy access to fee-based amenities: 5 swimming pools, a golf course, pickle ball courts as well as nearby kayaking, a winery, multiple restaurants and Berlin voted Best Little Town in the US!

4.91 out of 5 average rating, 174 reviews

Waterfront Beach Home in the Ocean City, MD Area

There is room for 8 adults (plus 2 kids). Located in the premiere seaside community in the Ocean City area, Ocean Pines, this wonderful waterfront home provides amazing views both day and night. The open floor plan provides guests with lots of room to socialize and bond, but also has secluded bedrooms that provides needed privacy. The outdoor living area is to die for. Sit back and watch the sun set over the canal while you catch up with friends or loved one. Use our bikes!

Superhost

4.83 out of 5 average rating, 126 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*

4.94 out of 5 average rating, 53 reviews

Ocean Pines MD Shady Rest Getaway

We Welcome you to Shady Rest Ocean Pines! My name is HC and I will be hosting you here at Shady Rest Ocean Pines along with my son Elijah. This property was our first family home and turning it into an Airbnb has allowed us to keep it in the family while sharing the tranquility that Ocean Pines has to offer to others. We hope you can create some memories here as we have as a family. Please enjoy your little Shady Rest Gateway! -From The Whaleys'

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Flats

Convenient locations with everyday essentials

Hotels

Stylish accommodation and amenities

Popular amenities for Ocean Pines holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Ocean Pines's top sights

Ocean Pines Golf Club15 locals recommend

River Run Golf Club & Community5 locals recommend

The Links at Lighthouse Sound16 locals recommend

Other great holiday rentals in Ocean Pines

4.89 out of 5 average rating, 38 reviews

Amazing and peaceful family fun 4 bedroom home

DerekRating, 5 stars1 week ago

This location was as described. The home was very clean and they provided the majority of the necessities needed for the stay. The host was quick to respond and provided excellent instructions on entry and other rules of the home. I would definitely stay here again.

4.98 out of 5 average rating, 41 reviews

Cottage in Ocean Pines

3-bedroom cottage in Ocean Pines

SylvainRating, 5 stars3 weeks ago

Viktoria's place was exactly what we were looking for. A three-bedroom place not far from Ocean City and Assateague, in a peaceful environment. Was super easy to go to both places during the long Week-End. The house was as advertised, spacious enough to accommodate the family but not too big. Next time we plan another WE in this area, we will certainly Viktoria's place again.

4.94 out of 5 average rating, 51 reviews

Home in Berlin

Amazing 2 Bedroom home close to the beach!

MikeRating, 5 stars7 months ago

We needed a small place to stay for a few days and this was the perfect place for the two of us; it was cozy, spotless, well equipped for all that we needed and the decor was beachy which was perfect for the area. Jacob was quick and attentive to any question we had - it was so quiet and peaceful outside. It was a perfect getaway for us - we would highly recommend to anyone needing a nice, quiet place in the future. Thank you!!!

4.97 out of 5 average rating, 34 reviews

WHAT DAY IS IT???????

KarinRating, 5 stars10 months ago

We had a wonderful stay at Brian’s place! The house was very comfortable, beautiful, clean and well equipped. The welcome basket and the baskets of samples in case you forgot something was a nice touch. He was very responsive to any questions I had. The beach parking pass was perfect - we took advantage of that on 2 days. I would definitely recommend this house. I wish we had more time at the house to enjoy it even more.

5 out of 5 average rating, 11 reviews

Waterfront Vacation Home in Ocean Pines

CarlosRating, 5 stars1 month ago

Great hosts & beautiful home. Extremely responsive & helpful with anything needed. Some of our guests arrived early & they didn't hesitate to respond to my messages & provide an update check in. Would highly recommend a stay. Beautiful area, great for a golf outing & a lot of good food places around.

4.86 out of 5 average rating, 29 reviews

Serene OP cottage perfect for your next getaway!

AllyyRating, 5 stars8 months ago

Jessica was very helpful and pleasant to communicate with. We came down for a concert series and did not want to stay right in the beach. Jessica’s place was the perfect ride away but perfect for us, quiet and peaceful. Thank you Jessica!

4.95 out of 5 average rating, 19 reviews

Penny's Place in the Pines

TeresaRating, 5 stars8 months ago

We felt at home the moment we arrived. Very clean and charming. Well equipped kitchen and plenty of bath necessities. The sunroom with coffee station was exceptional! Perfect spot to enjoy coffee the way you like it and every choice imaginable offered by the Host. The Hosts have thought of every need a guest would want and offers it graciously. Good communication and accommodations. Highly recommend!