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Chebeague Island Vacations

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

Hotwire can help you find your travel bliss with Chebeague 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 Chebeague 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 Chebeague 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 Chebeague Island well.

Top Hotel Deals

See all 236 Hotels in Chebeague Island
Chebeague Island Inn

Chebeague Island Inn

61 South Road, Chebeague Island
    4.0 out of 5.0
     
     

    Situated near the beach in Chebeague Island, this hotel is in the same area as Eagle Island State Park, Eartha and Wolfe's Neck State Park. Area attractions ...

    Ramada Plaza by Wyndham Portland

    Ramada Plaza by Wyndham 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 by Wyndham Portland$85

      Ramada Plaza by Wyndham Portland$85
      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 ...

        Fireside Inn & Suites$100

        Fireside Inn & Suites$100
        Super 8 by Wyndham Portland/Westbrook Area

        Super 8 by Wyndham Portland/Westbrook Area

        208 Larrabee Rd, Westbrook
          2.0 out of 5.0
           
           

          Situated in Westbrook, this motel is 0.8 mi (1.4 km) from Joker's Family Fun and Games and within 3 mi (5 km) of Riverside Municipal Golf Course and University ...

          Super 8 by Wyndham Portland/Westbrook Area$68

          Super 8 by Wyndham Portland/Westbrook Area$68
          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$145

            Hyatt Place Portland-Old Port$145
            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$94

              Clarion Hotel Portland$94
              Howard Johnson Hotel by Wyndham South Portland

              Howard Johnson Hotel by Wyndham 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 by Wyndham South Portland$81

                Howard Johnson Hotel by Wyndham South Portland$81
                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$84

                  Quality Suites$84
                  Residence Inn by Marriott Portland Downtown Waterfront

                  Residence Inn by Marriott Portland Downtown Waterfront

                  145 Fore Street, Portland
                    3.0 out of 5.0
                     
                     

                    Situated in the historical district, this hotel is within a 15-minute walk of Maine Narrow Gauge Railroad Company and Museum and Portland Observatory. Wadsworth-Longfellow ...

                    Residence Inn by Marriott Portland Downtown Waterfront$135

                    Residence Inn by Marriott Portland Downtown Waterfront$135
                    Days Inn by Wyndham Airport/Maine Mall

                    Days Inn by Wyndham Airport/Maine Mall

                    461 Maine Mall Rd, South Portland
                      2.0 out of 5.0
                       
                       

                      Situated near the airport, this hotel is within 1 mi (2 km) of Maine Mall and Sable Oaks Golf Course. Nonesuch River Golf Club and Tate House Museum are also ...

                      Days Inn by Wyndham Airport/Maine Mall$72

                      Days Inn by Wyndham Airport/Maine Mall$72

                      Top Flight Deals

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