Vacation rentals in Ocean Pines

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Ocean Pines

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Guest suite in Ocean Pines

4.95 out of 5 average rating, 353 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!

Nov. 17 – 24

$262 CAD per night

Guest favourite

Condo in Ocean Pines

4.96 out of 5 average rating, 106 reviews

Quiet Water View Condo

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

Mar. 5 – 12

$209 CAD per night

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.

May 8 – 15

$421 CAD per night

Guest favourite

Home in Ocean Pines

4.96 out of 5 average rating, 111 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.

Nov. 13 – 20

$252 CAD per night

Guest favourite

Guest suite in Ocean Pines

4.99 out of 5 average rating, 89 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.

Mar. 29 – Apr. 5

$212 CAD per night

Guest favourite

Home in Ocean View

4.92 out of 5 average rating, 531 reviews

Tiny House at Good Earth, near Bethany Beach

A custom-built "Tiny House" located right between our new dinner theater and our garden dining area. True to the show "Tiny House Nation"; cool interior with custom woodwork, stairs to a lofted bed. Fully functioning kitchen. Spacious bathroom & shower. We provide TVs and internet in the units but the quality of service is not guaranteed. We are in a rural area and sometimes it's slow or not working at all. If TV and internet are super important for your stay we may not be the right fit.

Apr. 27 – May 4

$189 CAD per night

Guest favourite

Condo in Ocean City

4.94 out of 5 average rating, 206 reviews

Awesome mid-town OC Location! Steps to the Beach!

This 3rd floor ocean-view condo is situated in a prime 36th Street mid-town location! Literally a few steps to the beach and close to everything... walk to Restaurants, Nightlife, Shopping, Boardwalk, Amusements, Convention Center and more! **Summer Months... ONLY Monday & Friday check-ins from Memorial Day to Labor Day. Book Weeks or Mini-weeks. (Weeks: Fri to Fri, OR Mon to Mon) (Mini-Weeks: Mon to Fri, OR Fri to Mon)** *Other months check in or out any night of the week*

Dec. 16 – 23

$171 CAD per night

Guest favourite

Condo in Ocean City

4.97 out of 5 average rating, 222 reviews

Direct Oceanfront with a View and Amenities Galore

Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with full 100% view of the beach and ocean.

Nov. 8 – 15

$199 CAD per night

Guest favourite

Guest suite in Berlin

4.99 out of 5 average rating, 148 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!

Dec. 24 – 31

$183 CAD per night

Guest favourite

Apartment in Frankford

4.98 out of 5 average rating, 121 reviews

Cozy Cottage Getaway

Enjoy this newly remolded 1 bedroom apartment tucked away on 2+ acres 3 miles from Bethany beach. Close to Rehobeth beach for outlet tax free shopping or Ocean City MD just 13 miles. You’ll be minutes away from lots of restaurants, stores, mini golf, arcade, night life etc. Property includes a 1/4 mile walking/running trail, fire pit and basket ball court. This is the perfect place to escape away from the busy Beach life but close enough to enjoy everything fully.

Apr. 23 – 30

$144 CAD per night

Guest favourite

Home in Ocean Pines

5.0 out of 5 average rating, 12 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'

Nov. 1 – 8

$188 CAD per night

Guest favourite

Cottage in Berlin

4.99 out of 5 average rating, 118 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.

Dec. 6 – 13

$264 CAD per night