Holiday rentals in Ocean Pines

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Top-rated holiday rentals in Ocean Pines

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Guest favourite

Apartment in Berlin

4.98 out of 5 average rating, 104 reviews

Amazing Waterfront in Berlin, MD- Sea Breeze Suite

1 of 5 waterfront units (Drift Inn, Sea Breeze, Coconut Grove, Coral Tides, Day Break) located at The Inn on Turville Creek in West Ocean City. Perfect for outdoor lovers or a quiet escape. Bring your paddleboards, kayaks, or just enjoy the beautiful views from the comfort of your own patio. The Inn is located approximately 5 miles from downtown Ocean City and the town of Berlin, MD (voted America's Coolest Small Town) and ~10 miles from Assateague. Stunning sunsets right from your front patio!

Guest favourite

Guest suite in Ocean Pines

4.95 out of 5 average rating, 356 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!

Guest favourite

Apartment in Ocean Pines

4.96 out of 5 average rating, 110 reviews

Peaceful Waterview Getaway

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

Guest favourite

Home in Ocean Pines

4.89 out of 5 average rating, 141 reviews

Relaxing Home Near the Beach in Ocean Pines, MD

This is a 3 bedroom/2 full bathroom, single-story, home that is ready for you and your dogs if you have them. Guests have use of the entire house, including an outdoor grill. There is a dog door that leads to a fenced backyard. Guests have access to our beach accessories and a free beach parking pass. The house can accommodate 6 people comfortably, and up to 8 with the use of a futon. The house has a stocked kitchen. The community has many amenities that are described in the house manual.

Guest favourite

Home in Ocean Pines

4.96 out of 5 average rating, 113 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.

Superhost

Apartment in Ocean City

4.84 out of 5 average rating, 145 reviews

Unit 2 on 41 St Ocean Side, Only 50 steps to beach

Dominica Beach is a 2-story building, just 50 paces to the sand dunes, with 12 large-sized studio condos. Each sleeps 4, has a private entrance, parking space, and balcony. LINENS, TOWELS, SOAPS/DETERGENTS, PAPER PRODUCTS INCLUDED. Guests have free access to Laundry, Beach & Baby items, Locked Storage & WiFi. Walk to restaurants, nightlife/Seacrets, Jolly Rogers Amusement/Water park, Convention Ctr. Great Beach (no hotels on 41st St)! Clean, Comfortable, Convenient Condos in Quiet Area.

Guest favourite

Apartment in Ocean City

4.99 out of 5 average rating, 103 reviews

Beautiful Renovated Ocean Front Condo 1b/1.5ba

Beautiful renovated ocean front condo. Get ready to relax in comfort and style! This large 836 sqft one 1b/1.5ba offers breath taking views of the ocean. You will be just steps away from the sand in one of the closest buildings to the beach. Enjoy your coffee or a different sunrise each day from your private balcony off the living room. Updated patio furniture with a cozy bench and high table with 2 chairs that bring a spectacular, completely unobstructed view of the beach and ocean.

Guest favourite

Tiny home in Selbyville

4.98 out of 5 average rating, 216 reviews

Destination Location! Farm Animals, Tours, Beaches

Scratch staying in a tiny house off your bucket list! Escape the Ocean City crowds and slow life down at this Garden Hideaway. Situated on a ranch just minutes from the beach, this unique home has a barnyard of fuzzy animals ready to greet you each day. Curated to both inspire joy and create presence, enjoy a simple morning and sip coffee with Fonzie the alpaca, Charlotte the mini-pig and a front yard of silly goats sure to entertain. This is a magical stay that we know you'll love!

Guest favourite

Home in Ocean Pines

4.99 out of 5 average rating, 102 reviews

Charming Waterfront Cottage w/2 King Suites + Dock

Newly renovated, sparkling, spacious house with room for 7 and waterfront views is waiting for you. Perfect for a single or double family getaway, girls weekend or quiet retreat. *Please note this is a No Smoking and No Pet Property. **We are located in a quiet residential neighborhood with lovely neighbors in close proximity. Please consider this when booking. ❤️ ***We do not supply sheets and towels. Ocean City Beach & Linen Rental have been popular with past guests.

Guest favourite

Guest suite in Berlin

4.99 out of 5 average rating, 151 reviews

Berlin/Ocean City Suite- Relax/Refresh near beach!

A remodeled, above garage guest suite separate from the main house in America's Coolest Small Town, Berlin Md! You will benefit from a separate entrance to your above garage suite which will allow you to enjoy your own quiet space to relax and embrace the small, quaint town of Berlin, all while a mere 15 minutes to the beaches of OCEAN CITY and Assateague! Multiple dining experiences and tons of shopping await you in either historic Berlin or world famous Ocean City!

Guest favourite

Cottage in Berlin

4.99 out of 5 average rating, 121 reviews

Bayfront Cottage w/ Amazing Views

Whether you’re enjoying time by the firepit or sipping coffee on the couch, the views of Sinepuxent Bay and Assateague Island make this cottage the ideal spot for your next vacation. The cottage is located in a quiet neighborhood and is only a short drive from Assateague Island, the historic town of Berlin, and the Ocean City Boardwalk.

Guest favourite

Flat in Ocean City

4.94 out of 5 average rating, 350 reviews

Private suite .5 mile from beach/no shared spaces

This spacious, private master suite is perfectly located on 116th street, half a mile from the beach and within walking distance to tons of shops and restaurants! Complete with a full bathroom, mini fridge, microwave, outdoor shower, and patio area, this cozy room is perfect for a relaxing beach getaway.