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Ocean Pines Vacations

Pack those stellar shades. We have Ocean Pines vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Ocean Pines – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Ocean Pines vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Ocean Pines

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Ocean Pines vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Ocean Pines well.

Top Hotel Deals

See all 1,087 Hotels in Ocean Pines
Villas of Ocean Pines

Villas of Ocean Pines

11029 Cathell Road, Berlin
    3.0 out of 5.0
     
     

    Located in Ocean Pines, this vacation home is within 3 mi (5 km) of River Run Golf Club, Casino at Ocean Downs, and Ocean Downs. Ocean Pines Golf and Country ...

    Whitecap Lane 9 4 Bedrooms 2.5 Bathrooms Home

    Whitecap Lane 9 4 Bedrooms 2.5 Bathrooms Home

    9 Whitecap Lane, Berlin
      3.5 out of 5.0
       
       

      This vacation home is located in Berlin (Ocean Pines), close to Ocean Pines Golf and Country Club, River Run Golf Club, and The Links at Lighthouse Sound. Area ...

      Ocean Pines on the Canal

      Ocean Pines on the Canal

      10 Beach Court, Berlin
        3.0 out of 5.0
         
         

        Located in Ocean Pines, this hotel is 1 mi (1.6 km) from Ocean Pines Golf and Country Club and 2.7 mi (4.4 km) from River Run Golf Club. Casino at Ocean Downs ...

        Frigate Run in Ocean Pines Apartment 4

        Frigate Run in Ocean Pines Apartment 4

        13 Frigate Run, Berlin
           
           

          This apartment building is located in Berlin (Ocean Pines), close to Ocean Pines Golf and Country Club, River Run Golf Club, and The Links at Lighthouse Sound. ...

          Windjammer Home 4 Bedrooms 3 Bathrooms Home

          Windjammer Home 4 Bedrooms 3 Bathrooms Home

          125 Windjammer Road, Berlin
            3.0 out of 5.0
             
             

            This vacation home is located in Berlin (Ocean Pines), close to Ocean Pines Golf and Country Club, River Run Golf Club, and Casino at Ocean Downs. Local attractions ...

            Fenwick Inn

            Fenwick Inn

            13801 Coastal Highway, Ocean City
              2.0 out of 5.0
               
               

              Situated by the ocean, this hotel is within a 15-minute walk of Lost Treasure Golf, Golf Down Under, and Fenwick Island Lighthouse. Transpeninsular Line Marker ...

              Fenwick Inn$47

              Fenwick Inn$47
              Grand Hotel & Spa

              Grand Hotel & Spa

              2100 N Baltimore Ave, Ocean City
                3.0 out of 5.0
                 
                 

                Located on the Ocean City Boardwalk, The Grand Hotel & Spa offers beach access and is within 2 miles of Roland E Powell Convention Center.

                Grand Hotel & Spa$57

                Grand Hotel & Spa$57
                Holiday Inn Ocean City

                Holiday Inn Ocean City

                6600 Coastal Hwy, Ocean City
                  3.0 out of 5.0
                   
                   

                  Located in Ocean City, this beachfront hotel is in the city center and within 2 mi (3 km) of Maui Golf, Ocean Plaza Mall Shopping Center, and Roland E. Powell ...

                  Holiday Inn Ocean City$60

                  Holiday Inn Ocean City$60
                  Dunes Manor

                  Dunes Manor

                  2800 Baltimore Ave, Ocean City
                    3.0 out of 5.0
                     
                     

                    Located in Midtown Ocean City, this resort is within a 15-minute walk of Ember's Island Miniature Golf and Planet Maze. Jolly Roger Amusement Park and Roland ...

                    Dunes Manor $44

                    Dunes Manor $44
                    Paradise Plaza Inn

                    Paradise Plaza Inn

                    3 Ninth Street, Ocean City
                      3.0 out of 5.0
                       
                       

                      Located in Ocean City, this beachfront hotel is on the boardwalk and within a 15-minute walk of Midway Shopping Center and Ocean Bowl Skate Park. Jolly Roger ...

                      Paradise Plaza Inn$59

                      Paradise Plaza Inn$59