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

Chianti Region Vacations

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

Hotwire can help you find your travel bliss with Chianti Region 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 Chianti Region

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 Chianti Region 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 Chianti Region well.

Top Hotel Deals

See all 1,418 Hotels in Chianti Region
Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA

Via del Puglia, 61, Figline Valdarno
    4.0 out of 5.0
     
     

    Located in the heart of Figline Valdarno, this hotel is 0.3 mi (0.5 km) from Franciscan Monastery of St. Francis and within 6 mi (10 km) of Museum of Terranuova ...

    Villa Casagrande Resort & SPA$123

    Villa Casagrande Resort & SPA$123
    Il Borgo di Vescine

    Il Borgo di Vescine

    Località Vescine, Radda in Chianti
      4.0 out of 5.0
       
       

      Situated in a rural location, this hotel is 3 mi (4.8 km) from Casa Vinicola Luigi Cecchi and within 6 mi (10 km) of Archaeological Museum of Chianti and Castello ...

      Il Borgo di Vescine$155

      Il Borgo di Vescine$155
      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 ...

        Villa I Barronci

        Villa I Barronci

        Via Sorripa 10, San Casciano in Val di Pesa
          4.0 out of 5.0
           
           

          These hotel accommodations are located throughout the area in San Casciano in Val di Pesa.

          La Loggia Villa Gloria

          La Loggia Villa Gloria

          Località Maciallina, Castelnuovo Berardenga
            3.0 out of 5.0
             
             

            Situated in a rural location, this hotel is within 6 mi (10 km) of University for Foreigners of Siena, Stadio Artemio Franchi, and Siena Stadium. Palasport Mens ...

            Borgo Del Cabreo

            Borgo Del Cabreo

            Via Monte Fioralle Case sparse, 9, Greve in Chianti
               
               

              Situated in Greve in Chianti, this property is within 1 mi (2 km) of Wine Museum and Piazza Matteotti. Passignano Abbey and Church of Santa Maria Assunta are ...

              Castello di Spaltenna

              Castello di Spaltenna

              Via Spaltenna 13, Gaiole in Chianti
                5.0 out of 5.0
                 
                 

                Situated in Gaiole in Chianti, this spa hotel is within a 15-minute walk of Gaiole in Chianti Stadium and Church of San Sigismondo. Medieval Tower of Barbischio ...

                Castello di Spaltenna$257

                Castello di Spaltenna$257
                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 ...

                  Hotel Certaldo

                  Hotel Certaldo

                  via del Molino, 74, Certaldo
                    4.0 out of 5.0
                     
                     

                    Situated on the riverwalk, this hotel is within 1 mi (2 km) of Casa del Boccaccio and Palazzo Pretorio. The SottoVico Garden and Castle of Oliveto are also within ...

                    Hotel Certaldo$104

                    Hotel Certaldo$104
                    CDH Hotel Radda

                    CDH Hotel Radda

                    Strada Statale 429, Radda in Chianti
                      4.0 out of 5.0
                       
                       

                      Situated in a rural location, this spa hotel is 3.1 mi (4.9 km) from Castello di Radda Winery and within 6 mi (10 km) of Castello d'Albola and Casa Vinicola ...

                      CDH Hotel Radda$105

                      CDH Hotel Radda$105

                      Top Flight Deals

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