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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 private bathroom
19–24 Oct
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4.95 out of 5 average rating, 418 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
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
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, 132 reviews
Guest favourite
Home in Ocean Pines
Water's Edge Retreat OCMD
4 bedrooms, 5 beds, 2.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 7 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
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
Superhost
Home in Ocean Pines
Dockside Oasis in Ocean Pines
3 bedrooms, 5 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Ocean Pines
Large Family Friendly Home in Ocean Pines
4 bedrooms, 7 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 15 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
The Nest
4 bedrooms, 5 beds, 3 bathrooms
7–12 Sept
4.86 out of 5 average rating, 7 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 Ocean Pines
Quiet Ocean Pines Retreat | Sleeps 8
3 bedrooms, 6 beds, 2 bathrooms
24–29 Aug
4.88 out of 5 average rating, 8 reviews
Top guest favourite
Home in Ocean Pines
Cozy home 8 miles from OCMD *Beach Pass Included*
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.99 out of 5 average rating, 71 reviews
Guest favourite
Home in Ocean Pines
Game Room! Waterfront Group Haven in Ocean Pines
6 bedrooms, 8 beds, 4 bathrooms
29 Aug – 3 Sept
4.96 out of 5 average rating, 55 reviews
Top guest favourite
Home in Ocean Pines
Manklin Creek Retreat | Water Views + Boat Dock
3 bedrooms, 4 beds, 2.5 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Cottage in Ocean Pines
3-bedroom cottage in Ocean Pines
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.99 out of 5 average rating, 79 reviews
Top guest favourite
Home in Ocean Pines
Unique Eastern Shore Retreat!
3 bedrooms, 3 beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 19 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