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Search results; Over 1,000 homes in Ocean Pines

Guest favourite
Home in Ocean Pines
Little house in Berlin, Md.
3 bedrooms, 6 beds, 2 private bathrooms
14–19 Sept
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4.95 out of 5 average rating, 146 reviews
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, 418 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
Guest favourite
Flat in Ocean Pines
Be our guest
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 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
23–28 Aug
5.0 out of 5 average rating, 18 reviews
Guest favourite
Cottage in Ocean Pines
Cozy Beach Getaway in the Lovely Ocean Pines North
3 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
4.9 out of 5 average rating, 209 reviews
Top guest favourite
Home in Bishopville
Charming countryside bungalow, just off the Beach!
1 bedroom, 2 beds, 1 bathroom
9–14 Sept
5.0 out of 5 average rating, 19 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, 667 reviews
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
Updated Ocean Pines Getaway w Fire Pit, Grill + Be
3 bedrooms, 4 beds, 2 bathrooms
26–31 May
5.0 out of 5 average rating, 10 reviews
Home in Ocean Pines
"Blue Crush" in popular Ocean Pines
4 bedrooms, 5 beds, 2.5 bathrooms
25–30 Aug
5.0 out of 5 average rating, 4 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
Top guest favourite
Home in Ocean Pines
Ocean Pines Escape
3 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
4.87 out of 5 average rating, 76 reviews
Home in Ocean Pines
14 Goldeneye Court
4 bedrooms, 6 beds, 2.5 bathrooms
30 Aug – 4 Sept
4.67 out of 5 average rating, 6 reviews
Home in Ocean Pines
beach time
5 bedrooms, 10 beds, 3 bathrooms
5–12 Sept
5.0 out of 5 average rating, 4 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
The Nest
4 bedrooms, 5 beds, 3 bathrooms
14–19 Sept
4.86 out of 5 average rating, 7 reviews
Top guest favourite
Home in Ocean Pines
hi-A-tus A-frame
2 bedrooms, 2 beds, 1.5 bathrooms
22–27 Aug
5.0 out of 5 average rating, 56 reviews
Home in Ocean Pines
Ocean Pines Retreat
3 bedrooms, 4 beds, 2 bathrooms
25–30 Aug
5.0 out of 5 average rating, 4 reviews