Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

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.

Portland Flight + Hotel packages

Top Hotel Deals

See all 185 Hotels in Portland
Heights Hotel

Heights Hotel

Yeates Road, Portland
    4.0 out of 5.0
     
     

    Situated near the beach in Portland, this eco-friendly hotel is close to Verne High Angle Battery, Royal Manor Theatre, and Broadcroft Quarry Nature Reserve. ...

    Heights Hotel$99

    Heights Hotel$99
    The Aqua

    The Aqua

    Castletown, Portland
      3.0 out of 5.0
       
       

      Situated in Portland, this hotel is 0.1 mi (0.1 km) from Weymouth Bay.

      The Aqua$66

      The Aqua$66
      Maritime Hotel

      Maritime Hotel

      Southwell Park, Portland
        3.5 out of 5.0
         
         

        Situated near the beach in Portland, this hotel is close to Portland Bill, Portland Bill Lighthouse and Church Ope Cove. Also nearby are Portland Museum and ...

        Maritime Hotel$80

        Maritime Hotel$80
        Beach House B&B

        Beach House B&B

        51 Chiswell, Portland
          3.0 out of 5.0
           
           

          Situated near the beach in Portland, this bed & breakfast is close to Royal Manor Theatre, Portland Castle and Weymouth and Portland National Sailing Academy. ...

          Beach House B&B$73

          Beach House B&B$73
          YHA Portland - Hostel

          YHA Portland - Hostel

          Hardy House, Castle Road, Portland
            3.0 out of 5.0
             
             

            Situated in Portland, this hostel is close to Portland Castle, Royal Manor Theatre, and Weymouth and Portland National Sailing Academy. Also nearby are Portland ...

            YHA Portland - Hostel$88

            YHA Portland - Hostel$88
            Thirtyfive B&B

            Thirtyfive B&B

            35 Easton Street, Portland
              4.0 out of 5.0
               
               

              Situated in a rural location, this bed & breakfast is close to Broadcroft Quarry Nature Reserve, Portland Museum, and Rufus Castle. Also nearby are Governor's ...

              Thirtyfive B&B$81

              Thirtyfive B&B$81
              199 Atlantic House

              199 Atlantic House

              Ayton Drive, Portland
                3.5 out of 5.0
                 
                 

                This Portland apartment building is set on the beach a short distance from Portland Castle, Portland Harbour, and Weymouth and Portland National Sailing Academy. ...

                Seapinks Cottage

                Seapinks Cottage

                47 Mallams, Portland
                  3.5 out of 5.0
                   
                   

                  Situated in Portland, this cottage is within a 10-minute walk of Royal Manor Theatre and Chesil Beach. Portland Castle and Weymouth Bay are also within 15 ...

                  Chesil View House

                  Chesil View House

                  19 ST MARTINS ROAD, Portland
                    3.5 out of 5.0
                     
                     

                    Situated in Portland, this cottage is within a 10-minute walk of Chesil Beach and Royal Manor Theatre. Verne High Angle Battery and Portland Castle are also ...

                    Portland Lodge Hotel

                    Portland Lodge Hotel

                    Easton Lane, Portland
                      3.0 out of 5.0
                       
                       

                      Situated in Portland, this bed & breakfast is within a 15-minute walk of Verne High Angle Battery and Broadcroft Quarry Nature Reserve. Chesil Beach and Royal ...

                      Portland Lodge Hotel$75

                      Portland Lodge Hotel$75

                      Top Flight Deals

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