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Search results; Over 1,000 homes in Ocean Pines

Top guest favourite
Guest suite in Ocean Pines
Stunning private waterfront suite
2 bedrooms, 3 beds, 1 bathroom
19–24 Oct
4.95 out of 5 average rating, 419 reviews
Top guest favourite
Home in Ocean Pines
Sweet Retreat
3 bedrooms, 4 beds, 2.5 bathrooms
14–19 Sept
4.97 out of 5 average rating, 114 reviews
Top guest favourite
Flat in Ocean Pines
Be our guest
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
4.98 out of 5 average rating, 64 reviews
Top guest favourite
Home in Ocean Pines
Cabin in the Pines I Luxury Touches + EV Charging
3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Bishopville
Charming countryside bungalow, just off the Beach!
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 21 reviews
Home in Ocean Pines
"Blue Crush" in popular Ocean Pines
4 bedrooms, 5 beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Cottage in Ocean Pines
Cozy Beach Getaway in the Lovely Ocean Pines North
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.9 out of 5 average rating, 209 reviews
Top guest favourite
Home in Ocean Pines
OC Gateway: Modern 4BR/2.5BA home (dog friendly)
4 bedrooms, 6 beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 88 reviews
Home in Ocean Pines
2 Decks & Pool Access: Ocean Pines Retreat
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
New place to stay
Top guest favourite
Home in Ocean Pines
Ocean Pines Retreat with Beach Club
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
4.99 out of 5 average rating, 133 reviews
Guest favourite
Home in Ocean Pines
Barefoot Pines Beach Retreat | Fire Pit + Grill
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.92 out of 5 average rating, 12 reviews
Home in Ocean Pines
14 Goldeneye Court
4 bedrooms, 6 beds, 2.5 bathrooms
13–18 Sept
4.67 out of 5 average rating, 6 reviews
Top guest favourite
Guest house in Ocean Pines
Studio Apartment above Garage
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 105 reviews
Top guest favourite
Home in Ocean Pines
Charming Waterfront Cottage w/2 King Suites + Dock
4 bedrooms, 7 beds, 3.5 bathrooms
12–17 Sept
4.99 out of 5 average rating, 146 reviews
Home in Ocean Pines
beach time
5 bedrooms, 10 beds, 3 bathrooms
5–12 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Guest suite in Berlin
Ayers Creek Carriage House
1 bedroom, 1 queen bed, 1 bathroom
24–29 Oct
4.97 out of 5 average rating, 669 reviews
Top guest favourite
Home in Ocean Pines
Home Away from Home , Pet friendly retreat
3 bedrooms, 3 beds, 2 bathrooms
24–29 Sept
4.88 out of 5 average rating, 106 reviews
Guest favourite
Home in Ocean Pines
Water's Edge Retreat OCMD
4 bedrooms, 5 beds, 2.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 7 reviews