Search form is loading

Celebrate cosy season — travel for up to £100 less this autumn with our vouchers.

Holidays to Castellina in Chianti 2026/2027

Plan your dream getaway with holidays to Castellina in Chianti, a hidden gem in the heart of Italy's famous wine country. Framed by rolling vineyards and filled with warm Italian hospitality, it's the perfect destination for food and wine lovers. Discover the mysteries of the ancient Etruscan civilization as you explore archaeological sites, or delve into the regional cuisine with authentic Tuscan cooking classes. Those seeking tranquility can find solace in the area's serene landscapes, while history enthusiasts can journey back in time, visiting fascinating museums and well-preserved medieval castles. Explore award-winning wineries and indulge in gourmet dining experiences in this food lover's paradise. For adventurous souls, the surrounding Chianti hills offer picturesque hiking and biking trails that aren't to be missed. With a holiday to Castellina in Chianti, you're signing up for more than just a vacation—it's an unforgettable journey filled with culture, history, gastronomy, and romance. Prepare for an excursion that'll enrich your senses and leave a permanent mark on your memory.

How does booking Flight + Hotel make travel even better?

Top holiday packages to Castellina in Chianti

  • from London, All airports (LON)
  • from Manchester, (MAN)
  • from Birmingham, (BHX)
  • from Bristol, International (BRS)
  • from Belfast, All airports (BFS)
  • from Glasgow, All airports (GLA)
  • Flight + Hotel

    Hotel Casafrassi

    rated as 3.5 out of 5 by 342 reviewers
    4 nightsFlights includedLondonbreakfast included
    3.83 mi from city centre
    from £137 pp
  • Flight + Hotel

    Hotel Belvedere Di San Leonino

    rated as 5 out of 5 by 887 reviewers
    4 nightsFlights includedLondon
    3.8 mi from city centre
    from £266 pp
  • Flight + Hotel

    Hotel Palazzo Squarcialupi

    rated as 4.5 out of 5 by 475 reviewers
    3 nightsFlights includedLondonbreakfast included
    1,060 ft from city centre
    from £496 pp
  • Flight + Hotel

    Borgo Di Pietrafitta Relais

    rated as 4 out of 5 by 316 reviewers
    3 nightsFlights includedLondon
    1.74 mi from city centre
    from £345 pp
  • Flight + Hotel

    Castello di Fonterutoli Wine Resort

    rated as 4 out of 5 by 283 reviewers
    4 nightsFlights includedLondonbreakfast included
    2.71 mi from city centre
    from £419 pp
  • Flight + Hotel

    Fattoria di Vegi

    rated as 5 out of 5 by 14 reviewers
    3 nightsFlights includedLondonbreakfast included
    3.09 mi from city centre
    from £600 pp
  • Flight + Hotel

    Hotel Colle Etrusco Salivolpi

    rated as 4.5 out of 5 by 740 reviewers
    4 nightsFlights includedLondon
    2,162 ft from city centre
    from £268 pp
  • Flight + Hotel

    Collelungo

    rated as 4.5 out of 5 by 154 reviewers
    3 nightsFlights includedLondon
    1.01 mi from city centre
    from £343 pp
  • Flight + Hotel

    Casa Vacanze Squarcialupi

    rated as 4.5 out of 5 by 5 reviewers
    4 nightsFlights includedLondon
    1,073 ft from city centre
    from £251 pp

Trusted by thousands of travellers

Cheap holidays to Castellina in Chianti

Book the best deals on holidays to Castellina in Chianti today!

  • from London, All airports (LON)
  • from Manchester, (MAN)
  • from Birmingham, (BHX)
  • from Bristol, International (BRS)
  • from Belfast, All airports (BFS)
  • from Glasgow, All airports (GLA)
  • Flight + Hotel

    Castello La Leccia

    rated as 5 out of 5 by 304 reviewers
    4 nightsFlights includedLondonbreakfast included
    2.25 mi from city centre
    from £363 pp
  • Flight + Hotel

    Albergo Il Colombaio

    rated as 4 out of 5 by 121 reviewers
    4 nightsFlights includedLondonbreakfast included
    591 ft from city centre
    from £305 pp
HOLIDAY TYPE:
City breaks
LANGUAGE:
Italian
CURRENCY:
Euro (€)
AVG FLIGHT TIME:
2h 5m (from London)
NEAREST AIRPORT:
FLR, 23.0 mi
Florence Airport Airport

Our most popular holiday packages to Castellina in Chianti

  • from London, All airports (LON)
  • from Manchester, (MAN)
  • from Birmingham, (BHX)
  • from Bristol, International (BRS)
  • from Belfast, All airports (BFS)
  • from Glasgow, All airports (GLA)
  • Flight + Hotel

    Locanda Le Piazze

    rated as 5 out of 5 by 803 reviewers
    Flights included
    3 mi from city centre
  • Flight + Hotel

    Villa Casalecchi Country Hotel

    rated as 4.5 out of 5 by 214 reviewers
    Flights included
    1.33 mi from city centre

Travel tips for Castellina in Chianti

Your Castellina in Chianti questions answered

  • What are the most popular places to visit while in Castellina in Chianti?

    The most popular places to visit in Castellina in Chianti are: Montecalvario, Castellina Fortress, Mazzei Winery.

  • What kind of holidays does Castellina in Chianti offer?

    Castellina in Chianti is the ideal destination for city breaks.

  • How long does it take to fly from the UK to Castellina in Chianti?

    The exact flight duration to Castellina in Chianti varies depending on the departure airport in the UK. It takes approximately 2h5m to fly from London to Castellina in Chianti.

  • Why should I book a flight & hotel package to Castellina in Chianti on lastminute.com?

    Booking a flight + hotel package to Castellina in Chianti with lastminute.com offers several advantages. By booking both services together, you can take advantage of exclusive deals and choose from thousands of flights and accommodations for the perfect combination. Additionally, you can secure your vacation with a deposit and pay the remaining amount later. You also have the flexibility to add other travel extras such as insurance, rental cars, and luggage to the flight + hotel package as per your preferences.

  • Do I need a Visa to go to Castellina in Chianti?

    Before travelling from the UK to Castellina in Chianti, ensure your passport is valid for the duration of your stay. To get the latest Visa information for Castellina in Chianti, please check travel advice on GOV.UK.