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Castellina in Chianti Vacations

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

Hotwire can help you find your travel bliss with Castellina in Chianti 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 Castellina in Chianti

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 Castellina in Chianti 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 Castellina in Chianti well.

Top Hotel Deals

See all 4,704 Hotels in Castellina in Chianti
Locanda le Piazze

Locanda le Piazze

Localita Le Piazze 41, Castellina in Chianti
    4.0 out of 5.0
     
     

    Situated in Castellina in Chianti, this hotel is within 16 mi (25 km) of Piazza della Cisterna, Sant'Agostino Church, and Piazza Duomo. Castello di Radda Winery ...

    Borgo di Pietrafitta Relais

    Borgo di Pietrafitta Relais

    Pietrafitta Società Agricola a r.l, Castellina in Chianti
       
       

      Situated in a rural location, this farm stay is 2.4 mi (3.9 km) from Casa Vinicola Luigi Cecchi and 2.6 mi (4.2 km) from Archaeological Museum of Chianti. Church ...

      Castello di Fonterutoli

      Castello di Fonterutoli

      Via Puccini 4, Castellina in Chianti
         
         

        Located in the historical district, this family-friendly bed & breakfast is within 12 mi (20 km) of Monteriggioni Castle, Basilica di San Domenico, and Basilica ...

        Castello La Leccia

        Castello La Leccia

        Località La Leccia, Castellina in Chianti
           
           

          Situated in Castellina in Chianti, this spa farm stay is 2.4 mi (3.9 km) from Casa Vinicola Luigi Cecchi and within 9 mi (15 km) of The Rock of Staggia and Isole ...

          Hotel Casafrassi

          Hotel Casafrassi

          loc. Casafrassi - via chiantigiana, 40, Castellina in Chianti
            4.0 out of 5.0
             
             

            Located in a rural location, this family-friendly hotel is within 9 mi (15 km) of Casa Vinicola Luigi Cecchi, Enoteca Italiana, and Archaeological Museum of ...

            Hotel Casafrassi$86

            Hotel Casafrassi$86
            Tenuta Di Ricavo

            Tenuta Di Ricavo

            Località Ricavo, 4, Castellina in Chianti
              4.0 out of 5.0
               
               

              Situated in a rural location, this hotel is within 3 mi (5 km) of Casa Vinicola Luigi Cecchi, Archaeological Museum of Chianti, and Isole e Olena Winery. Chianti ...

              Collelungo

              Collelungo

              Loc. Collelungo 12/14, Castellina in Chianti
                 
                 

                Situated in Castellina in Chianti, this farm stay is 2.4 mi (3.8 km) from Casa Vinicola Luigi Cecchi and 2.6 mi (4.2 km) from Archaeological Museum of Chianti. ...

                Hotel Colle Etrusco Salivolpi

                Hotel Colle Etrusco Salivolpi

                Via Fiorentina 89, Castellina in Chianti
                  3.0 out of 5.0
                   
                   

                  Situated in a rural location, this hotel is within a 15-minute walk of Casa Vinicola Luigi Cecchi and Archaeological Museum of Chianti. Isole e Olena Winery ...

                  Querceto di Castellina

                  Querceto di Castellina

                  Località Querceto 9, Castellina in Chianti
                     
                     

                    Situated in Castellina in Chianti, this country house is within 6 mi (10 km) of Casa Vinicola Luigi Cecchi, Archaeological Museum of Chianti, and Church of Santa ...

                    Borgo Sicelle

                    Borgo Sicelle

                    Localita Sicelle 59, Castellina in Chianti
                       
                       

                      Situated in a rural location, this residence is within 6 mi (10 km) of Chianti Observatory, Isole e Olena Winery, and Church of Santa Maria Assunta. Il Molino ...

                      Top Flight Deals

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