Ocean Pines waterfront stays

5 waterfront vacation rentals in Ocean Pines, MD from Whimstay, from $212 a night, each on the water by its own description. Part of our Ocean City coverage.

Rates are each listing's own "from" price on 4 August 2026; the booking page shows live prices and dates. Looking for the houses we would book ourselves? The curated Ocean City list.

Showing 1 to 5 of 5. Best rated first, then price.

Waterfront Cottage w/ Private Dock in Ocean Pines!, Ocean Pines, MD from $315

Waterfront Cottage w/ Private Dock in Ocean Pines!

Canal front Entire cottage 3 bed 2 bath sleeps 7
Ocean Pines, MDrated 5.0
Game Room! Waterfront Group Haven in Ocean Pines, Ocean Pines, MD from $1,004

Game Room! Waterfront Group Haven in Ocean Pines

Waterfront Entire home 6 bed 4 bath sleeps 13 pets ok
Ocean Pines, MDrated 5.0
Boat Dock! Waterfront Group Getaway in Ocean Pines, Ocean Pines, MD from $374

Boat Dock! Waterfront Group Getaway in Ocean Pines

Waterfront Entire home 4 bed 4 bath sleeps 10 pets ok
Ocean Pines, MDrated 4.9
Furnished Deck! Waterfront Ocean Pines Home, Ocean Pines, MD from $212

Furnished Deck! Waterfront Ocean Pines Home

Waterfront Entire home 2 bed 2 bath sleeps 5
Ocean Pines, MDrated 4.8
Waterfront Ocean Pines Home Golf Course views!, Ocean Pines, MD from $467

Waterfront Ocean Pines Home Golf Course views!

Waterfront Vacation Rental 5 bed 4 bath sleeps 12
Ocean Pines, MD
The curated list

Ocean City the way we would book it: a short list of houses we checked for real water access.

Open the Ocean City guide →
Every shore

Ten shores, each with its own stays list and curated picks.

All beach stays →

Affiliate disclosure: Sleep By The Beach earns a commission when you book through Whimstay, Vrbo or Booking.com links on this page, at no extra cost to you. Listing details and photos come from the Whimstay feed and belong to the hosts. How we work.

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