Vacation rentals in Ocean Pines

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Top-rated vacation rentals in Ocean Pines

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

Guest favourite

Condo in Ocean City

4.91 out of 5 average rating, 174 reviews

**Beautiful newly renovated OC MD water view home*

Beautiful Bay view ground floor unit steps away from the water, 1 free parking spot available for guests and tons of street parking comfortable for 2 people for a long stay and 4 for a weekend getaway Located in the middle of all Ocean city major attractions Walking distance to the beach and Jolly Roger Amusement water Park and tons of other activities and restaurants. 6 min away from famous Seacrets, Macky’s & Fish Tales 8 min drive to OC famous board walk & downtown 15 min to Shopping Outlets

Apr. 23 – 30

$159 CAD per night
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!

Dec. 10 – 17

$268 CAD per night
Guest favourite

Condo in Ocean Pines

4.96 out of 5 average rating, 102 reviews

Peaceful Water View Retreat

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

Nov. 2 – 9

$228 CAD per night

Popular amenities for Ocean Pines vacation rentals

Stay near Ocean Pines's top sights

Ocean Pines Yacht Club & Marina28 locals recommend
Abi's Diner4 locals recommend
Southgate Grill14 locals recommend
DeNovo's Trattoria8 locals recommend
A Bagel And ...14 locals recommend
Plaza Tapatia5 locals recommend

Other great vacation rentals in Ocean Pines

Superhost

Home in Berlin

4.86 out of 5 average rating, 44 reviews

2BR home close to beach in "coolest" town

Apr. 23 – 30

$120 CAD per night
Superhost

Home in Ocean Pines

5.0 out of 5 average rating, 12 reviews

Nottingham Beach Retreat

Apr. 28 – May 5

$216 CAD per night
Guest favourite

Home in Berlin

5.0 out of 5 average rating, 33 reviews

Amazing 2 Bedroom home close to the beach!

Nov. 12 – 19

$147 CAD per night
Guest favourite

Vacation home in Ocean Pines

5.0 out of 5 average rating, 8 reviews

Cozy Stay by the Bay

Dec. 6 – 13

$278 CAD per night
Guest favourite

Home in Ocean Pines

4.95 out of 5 average rating, 19 reviews

Peace of Heaven

May 8 – 15

$242 CAD per night
Guest favourite

Home in Ocean Pines

4.96 out of 5 average rating, 57 reviews

Cozy home on quiet court; 10 mins from Ocean City

Oct. 18 – 25

$302 CAD per night
Guest favourite

Home in Ocean Pines

4.81 out of 5 average rating, 59 reviews

Pet friendly 2 Bedroom Townhouse on a Golf Course

Nov. 11 – 18

$284 CAD per night
Guest favourite

Home in Ocean Pines

5.0 out of 5 average rating, 10 reviews

Pinehurst Beach House

Dec. 13 – 20

$335 CAD per night
Guest favourite

Home in Ocean Pines

5.0 out of 5 average rating, 98 reviews

Charming Waterfront Cottage w/2 King Suites + Dock

Apr. 19 – 26

$526 CAD per night
Guest favourite

Home in Berlin

5.0 out of 5 average rating, 24 reviews

Rest warm; rest well at Clifton Retreat in Berlin

May 28 – Jun. 4

$181 CAD per night
Guest favourite

Home in Ocean Pines

5.0 out of 5 average rating, 9 reviews

Peaceful, pet and family-friendly beach retreat

Nov. 17 – 24

$277 CAD per night
Guest favourite

Home in Ocean Pines

4.96 out of 5 average rating, 27 reviews

Waterfront w/Dock, Rooftop Terrace & 2 Kings

Aug. 14 – 21

$1,316 CAD per night

Quick stats about vacation rentals in Ocean Pines

Total rentals

260 properties

Rentals with a pool

140 properties have a pool

Pet-friendly rentals

70 properties allow pets

Family-friendly rentals

240 properties are a good fit for families

Total number of reviews

6.4K reviews

Nightly prices starting at

$68 CAD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Maryland
  4. Worcester County
  5. Ocean Pines