Holiday rentals with a fire pit in Ocean Pines

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!

Ranch Stay- Farm Animals, Jacuzzi, Arcade, Beaches

Welcome to the Swedish Cowboy, your ultimate escape! This unique BARNDOMINIUM home is designed to offer a memorable retreat for up to four (4) guests, with the flexibility to accommodate two (2) additional guests for a small fee. Enjoy the charming backyard where you can meet a variety of fuzzy and feathered friends or head inside and play on the arcade or relax in the jacuzzi. Perfectly situated near popular beaches and bustling boardwalks, you'll have plenty of options for fun and relaxation.

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!

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.

19th Century Coastal Cottage with Modern Amenities

Built from “clinker bricks” in 1941 to house poultry feed, this Airbnb is a dreamy place to slow down. Exposed wood beams and interior brick walls as well as all the luxuries required for a rural escape. This charming cottage near the beach & is surrounded by enchanted gardens. You will swoon over the carved marble bathtub and gorgeous living areas. Perfect for a romantic getaway, Hobbs and Rose Cottage is waiting to create a memorable experience for you! NEW for 2025, our mediation room!

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.

Relax at the Shorehouse

Our cozy, rustic, beachy apartment is close to all the area has to offer! We are nestled between Snow Hill and historic Berlin off Rt 113. We are about 15 min from West Ocean City and 12 miles from Assateague. Dining, shopping, and family activites are also nearby including a public boat ramp 5 min away to launch small watercraft and a playground with pavilion across the street. We recently renovated the apartment, and the decor was chosen to make guests feel at home at the Shorehouse!

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.

Delightful Skoolie Near Bethany Beach

Try tiny living! Come to the Delaware beach for a unique glamping experience. The Coastal Cruiser is a 1985 Thomas School Bus turned tiny home. Spend your days exploring the Delaware Coast and come home to a rustic Skoolie with a full kitchen & outdoor area. You have access to fire pit, grill, and outdoor seating area. We’ve renovated- there is a bunk bed, and a full bathroom with toilet, shower, and sink. The bathroom is in a separate building about 20 ft from the bus.

Seaside Sunroom, No cleaning fee, No Wi-Fi.

Bright small space, attached to main house, but has it's own entrance. Room has a queen bed, full bathroom with tub, Keureg style coffee maker, mini fridge; live plants in room, 7 min drive to Bethany Beach. View and access to backyard seating, chimnea, No WIFI, no TV. Beach gear available.There is no access to or from main house, but some muffled noise can be heard during the day, including a small dog. Self check in with a key, but no late check in, please, ty!

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.

Farm Cottage - POOL - 30 Min to BEACH

Enjoy this beautiful cottage/studio apartment. Perfect little getaway space for 2 (or 3). Our little cottage is surrounded by fields and the quiet sound of country sunrise. You'll wake up to chickens anxious to get out of their coop or Lucy, the turkey, peeking in your window. In the evenings, light the firepit or enjoy and a quiet nighttime swim with our duck. And our very friendly dog, Tanka (Cane Corso) will welcome you to our family.