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Portland Vacations

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

Hotwire can help you find your travel bliss with Portland 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 Portland

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 Portland 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 Portland well.

Top Hotel Deals

See all 178 Hotels in Portland
Maritime Hotel

Maritime Hotel

Southwell Park, Portland
    3.5 out of 5.0
     
     

    Situated near the beach, this hotel is within 2 mi (3 km) of Portland Museum, Church Ope Cove, and Rufus Castle. Portland Bill Lighthouse and Durdle Pier are ...

    Heights Hotel

    Heights Hotel

    Yeates Road, Portland
      3.0 out of 5.0
       
       

      Situated near the beach, this eco-friendly hotel is within a 15-minute walk of Royal Manor Theatre and Verne High Angle Battery. Broadcroft Quarry Nature Reserve ...

      Beach House B&B

      Beach House B&B

      51 Chiswell, Portland
        3.0 out of 5.0
         
         

        Situated near the beach, this bed & breakfast is within a 10-minute walk of Royal Manor Theatre and Chesil Beach. Portland Castle and Weymouth and Portland National ...

        The Aqua

        The Aqua

        Castletown, Portland
          3.0 out of 5.0
           
           

          Situated in Portland, this hotel is within a 15-minute walk of Portland Castle, Royal Manor Theatre, and Chesil Beach. Weymouth and Portland National Sailing ...

          No.35 at The New Inn Portland

          No.35 at The New Inn Portland

          35 Easton Street, Portland
            4.0 out of 5.0
             
             

            Situated in a rural location, this inn is within a 15-minute walk of Broadcroft Quarry Nature Reserve and Portland Museum. Governor's Community Garden and Verne ...

            YHA Portland - Hostel

            YHA Portland - Hostel

            Hardy House, Castle Road, Portland
              3.0 out of 5.0
               
               

              Situated in Portland, this hostel is within a 10-minute walk of Portland Castle, Royal Manor Theatre, and Chesil Beach. Portland Harbour and Weymouth and Portland ...

              199 Atlantic House

              199 Atlantic House

              Ayton Drive, Portland
                3.5 out of 5.0
                 
                 

                Situated on the beach, this apartment building is within a 15-minute walk of Portland Castle, Portland Harbour, and Chesil Beach. Weymouth and Portland National ...

                Chesil View House

                Chesil View House

                19 ST MARTINS ROAD, Portland
                  3.5 out of 5.0
                   
                   

                  Situated in Portland, this cottage is close to Royal Manor Theatre, Verne High Angle Battery, and Portland Castle. Also nearby are Broadcroft Quarry Nature Reserve ...

                  Seapinks Cottage

                  Seapinks Cottage

                  47 Mallams, Portland
                    3.5 out of 5.0
                     
                     

                    Situated in Portland, this cottage is close to Royal Manor Theatre, Verne High Angle Battery, and Portland Castle. Also nearby are Weymouth and Portland National ...

                    Best Western Weymouth Hotel Rembrandt

                    Best Western Weymouth Hotel Rembrandt

                    Dorchester Road, Weymouth
                      3.0 out of 5.0
                       
                       

                      Situated by the sea, this hotel is within 1 mi (2 km) of Pirate Adventure Mini Golf, Weymouth Marina, and Radipole Lake Nature Reserve. Sea Life Park and Weymouth ...

                      Best Western Weymouth Hotel Rembrandt$111

                      Best Western Weymouth Hotel Rembrandt$111