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Bailey Island Vacations

Pack those stellar shades. We have Bailey Island 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 Bailey Island – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Bailey Island 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 Bailey Island

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 Bailey Island 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 Bailey Island well.

Top Hotel Deals

See all 229 Hotels in Bailey Island
Ramada Plaza Portland

Ramada Plaza Portland

155 Riverside St, Portland
    3.0 out of 5.0
     
     

    Situated near the airport, this hotel is 0.7 mi (1.1 km) from Joker's Family Fun and Games and within 3 mi (5 km) of Riverside Municipal Golf Course and University ...

    Ramada Plaza Portland$72

    Ramada Plaza Portland$72
    Fireside Inn & Suites

    Fireside Inn & Suites

    81 Riverside St, Portland
      3.0 out of 5.0
       
       

      This family-friendly Portland hotel is located near the airport, within 3 mi (5 km) of Joker's Family Fun and Games, Southworth Planetarium and Riverside Municipal ...

      Hyatt Place Portland-Old Port

      Hyatt Place Portland-Old Port

      433 Fore St, Portland
        3.0 out of 5.0
         
         

        Located in Downtown Portland, this hotel is within a 10-minute walk of Casco Bay Lines Ferry Terminal, Wadsworth-Longfellow House, and Victoria Mansion. Portland ...

        Hyatt Place Portland-Old Port$108

        Hyatt Place Portland-Old Port$108
        Clarion Hotel Portland

        Clarion Hotel Portland

        1230 Congress St, Portland
          3.0 out of 5.0
           
           

          Situated near the airport, this hotel is within a 15-minute walk of Thompson's Point, Hadlock Field, and Portland Exposition Building. Victoria Mansion is 1.6 ...

          Clarion Hotel Portland$89

          Clarion Hotel Portland$89
          Howard Johnson Hotel South Portland

          Howard Johnson Hotel South Portland

          675 Main Street I-95, South Portland
            2.0 out of 5.0
             
             

            Situated in South Portland, this hotel is within 3 mi (5 km) of Maine Military Museum, Maine Mall, and Sable Oaks Golf Course. Victoria Mansion and Portland ...

            Howard Johnson Hotel South Portland$63

            Howard Johnson Hotel South Portland$63
            Quality Suites

            Quality Suites

            500 Us Route 1, Freeport
              2.5 out of 5.0
               
               

              Situated in Freeport, this hotel is within 3 mi (5 km) of LL Bean Flagship Store, Desert of Maine, and Eartha. Wolfe's Neck Farm and Brunswick Golf Club are ...

              Quality Suites$70

              Quality Suites$70
              Courtyard Portland Downtown/Waterfront

              Courtyard Portland Downtown/Waterfront

              321 Commercial St, Portland
                3.0 out of 5.0
                 
                 

                Located in Downtown Portland, this hotel is within a 10-minute walk of Cumberland County Civic Center, Victoria Mansion, and Wadsworth-Longfellow House. Portland ...

                Courtyard Portland Downtown/Waterfront$113

                Courtyard Portland Downtown/Waterfront$113
                The Press Hotel, Marriott Autograph Collection

                The Press Hotel, Marriott Autograph Collection

                119 Exchange Street, Portland
                  4.0 out of 5.0
                   
                   

                  Located in Downtown Portland, this hotel is within a 10-minute walk of Merrill Auditorium, Wadsworth-Longfellow House, and Children's Museum of Maine. Portland ...

                  The Press Hotel, Marriott Autograph Collection$119

                  The Press Hotel, Marriott Autograph Collection$119
                  DoubleTree by Hilton Hotel Portland

                  DoubleTree by Hilton Hotel Portland

                  363 Maine Mall Rd, South Portland
                    3.5 out of 5.0
                     
                     

                    Located directly accross from the Maine Mall with easy access to all major highways, Portland International Jetport and just minutes to Portlands old port, our ...

                    Portland Harbor Hotel

                    Portland Harbor Hotel

                    468 Fore Street, Portland
                      4.0 out of 5.0
                       
                       

                      Located in Downtown Portland, this hotel is within a 10-minute walk of Cumberland County Civic Center, Wadsworth-Longfellow House, and Victoria Mansion. Portland ...

                      Top Flight Deals

                      Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.