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Pienza Vacations

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

Hotwire can help you find your travel bliss with Pienza 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 Pienza

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 Pienza 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 Pienza well.

Top Hotel Deals

See all 1,784 Hotels in Pienza
Hotel Relais II Chiostro di Pienza

Hotel Relais II Chiostro di Pienza

Corso Rossellino 26, Pienza
    4.0 out of 5.0
     
     

    Situated in Pienza, this romantic hotel is steps from Piazza Pio II, Pienza Cathedral, and Palazzo Piccolomini. Palazzo Comunale and Museo Diocesano are also ...

    Hotel Relais II Chiostro di Pienza$62

    Hotel Relais II Chiostro di Pienza$62
    Hotel Corsignano

    Hotel Corsignano

    Via Della Madonnina 11, Pienza
      4.0 out of 5.0
       
       

      Situated in Pienza, this hotel is within a 10-minute walk of Palazzo Comunale, Pienza Cathedral, and Palazzo Piccolomini. Piazza Pio II and Palazzo Borgia are ...

      Hotel Corsignano$97

      Hotel Corsignano$97
      Antica Locanda

      Antica Locanda

      Corso Il Rossellino, 72, Pienza
         
         

        Situated in the historical district, this townhouse accommodation is steps from Palazzo Comunale, Pienza Cathedral, and Palazzo Piccolomini. Palazzo Borgia and ...

        Hotel Residence San Gregorio

        Hotel Residence San Gregorio

        Via Della Madonnina 4, Pienza
          3.0 out of 5.0
           
           

          Located in the heart of Pienza, this residence is within a 5-minute walk of Palazzo Comunale and Pienza Cathedral. Palazzo Piccolomini is 0.3 mi (0.5 km) ...

          Tenuta Santo Pietro

          Tenuta Santo Pietro

          Localita Santo Pietro 29, Pienza
             
             

            Situated in Pienza, this farm stay is within 6 mi (10 km) of Val d'Orcia, Pienza Cathedral, and Palazzo Piccolomini. Piazza Pio II and Museo Diocesano are also ...

            A440 in Tuscany

            A440 in Tuscany

            Podere Favolello Località Porciano, Pienza
               
               

              Situated in a regional park, this farm stay is close to Pieve di Corsignano, Palazzo Piccolomini, and Pienza Cathedral. Also nearby are Piazza Pio II and Palazzo ...

              Agriturismo Chiancianello

              Agriturismo Chiancianello

              Localita' la Vittoria 92, Pienza
                 
                 

                Situated in a regional park, this farm stay is within 9 mi (15 km) of Piscine Termali Theia, Palazzo Piccolomini, and Parco Acqua Santa. Chianciano Art Museum ...

                L'Olmo

                L'Olmo

                SP 88 Orcia delle Macchie, Pienza
                   
                   

                  Situated in Pienza, this townhouse accommodation is 2.8 mi (4.6 km) from Pienza Cathedral and 2.9 mi (4.6 km) from Palazzo Piccolomini. Palazzo Borgia and Palazzo ...

                  Agriturismo Il Colombaiolo

                  Agriturismo Il Colombaiolo

                  Podere Colombaiolo 12, Pienza
                     
                     

                    Situated in a rural location, this farm stay is within a 15-minute walk of Pieve di Corsignano and Palazzo Piccolomini. Pienza Cathedral is 0.6 mi (1 km) ...

                    Agriturismo Il Macchione

                    Agriturismo Il Macchione

                    S.P. 71 Per S. Anna in Camprena, Pienza
                       
                       

                      Situated near the airport, in Pienza, this hotel is in the same area as Palazzo Piccolomini, Pienza Cathedral, and Horti Leonini. Area attractions also include ...

                      Top Flight Deals

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