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Gloucester Vacations

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

Hotwire can help you find your travel bliss with Gloucester 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 Gloucester

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 Gloucester 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 Gloucester well.

Gloucester Flight + Hotel packages

Top Hotel Deals

See all 161 Properties in Gloucester
Beauport Hotel Gloucester

Beauport Hotel Gloucester

55 Commercial Street, Gloucester
    3.5 out of 5.0
     
     

    Located in Gloucester, this beachfront hotel is in the historical district and within a 10-minute walk of Fishermen's Memorial Monument and Sargent House Museum. ...

    Beauport Hotel Gloucester$195

    Beauport Hotel Gloucester$195
    The Vista

    The Vista

    22 Thatcher Rd., Gloucester
      2.5 out of 5.0
       
       

      Situated by the ocean, this hotel is within a 10-minute walk of Cape Ann and Good Harbor Beach. Long Beach and Schooner Adventure are also within 1 mi (2 ...

      The Vista$239

      The Vista$239
      Sea Lion Motel and Cottages

      Sea Lion Motel and Cottages

      138 Eastern Avenue, Gloucester
        2.5 out of 5.0
         
         

        Situated near the beach, this motel is within 1 mi (2 km) of Cape Ann, Good Harbor Beach, and Schooner Adventure. Long Beach and Maritime Gloucester are also ...

        Sea Lion Motel and Cottages$189

        Sea Lion Motel and Cottages$189
        Ocean House Hotel at Bass Rocks

        Ocean House Hotel at Bass Rocks

        107 Atlantic Rd, Gloucester
          4.0 out of 5.0
           
           

          Situated on the waterfront, this hotel is within 2 mi (3 km) of Good Harbor Beach, Cape Ann, and Gloucester Stage Company. Schooner Adventure and Niles Beach ...

          Ocean House Hotel at Bass Rocks$316

          Ocean House Hotel at Bass Rocks$316
          Atlantis Oceanfront Inn

          Atlantis Oceanfront Inn

          125 Atlantic Road, Gloucester
            3.0 out of 5.0
             
             

            Situated by the ocean, this motel is within 2 mi (3 km) of Good Harbor Beach, Cape Ann, and Gloucester Stage Company. Schooner Adventure and Niles Beach are ...

            Atlantis Oceanfront Inn$225

            Atlantis Oceanfront Inn$225
            Cape Ann's Marina Resort

            Cape Ann's Marina Resort

            75 Essex Avenue, Gloucester
              3.5 out of 5.0
               
               

              Situated near the beach, this resort is within a 15-minute walk of Fishermen's Memorial Monument and Stage Fort Park. Half Moon Beach and Sargent House Museum ...

              Cape Ann's Marina Resort$168

              Cape Ann's Marina Resort$168
              Harborview Inn

              Harborview Inn

              71 Western Avenue, Gloucester
                4.0 out of 5.0
                 
                 

                Situated near the beach, this romantic bed & breakfast is within a 15-minute walk of Fishermen's Memorial Monument, Sargent House Museum, and Stage Fort Park. ...

                Harborview Inn$229

                Harborview Inn$229
                Castle Manor Inn

                Castle Manor Inn

                141 Essex Avenue, Gloucester
                  2.5 out of 5.0
                   
                   

                  Situated by the ocean, this inn is within 1 mi (2 km) of Fishermen's Memorial Monument, Stage Fort Park, and Half Moon Beach. Sargent House Museum and Cape Ann ...

                  Castle Manor Inn$145

                  Castle Manor Inn$145
                  Atlantic Highlands Apartment Apartment 1

                  Atlantic Highlands Apartment Apartment 1

                  6 Old Salem Rd - cottage, Gloucester
                    3.5 out of 5.0
                     
                     

                    Situated in Gloucester, this apartment building is within a 10-minute walk of Half Moon Beach and Stage Fort Park. Fishermen's Memorial Monument and Ravenswood ...

                    A Glamorous Gloucester Getaway Apartment 3

                    A Glamorous Gloucester Getaway Apartment 3

                    82 Bass Ave, Gloucester
                      3.5 out of 5.0
                       
                       

                      Situated in Gloucester, this apartment building is within a 15-minute walk of Good Harbor Beach and Cape Ann. Schooner Adventure and Maritime Gloucester are ...

                      Top Flight Deals

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