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A stone building with a clock tower, steps leading up to it, and people walking around.

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    Check prices for these dates

    Check prices for these dates, 13 – 14 December 2026

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    Our top choices for Castellina in Chianti holiday homes

    1. Agriturismo La Ferrozzola

    A stone building with a tiled roof, surrounded by greenery and a large terracotta pot.

    2. Casa Marisa in Castellina in Chianti

    A brick building with a garden, a metal fence, and a clear sky.

    3. LARGE, OPEN-AIR TERRACE WITH VIEWS OF THE CHAINTI VALLEY AND DRINKS

    A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

    4. Chianti Craft House Badia a Passignano

    A view through a wooden door of a courtyard with stone walls and potted plants.

    5. Siena Love Nest: Romantic Suite with Spa & Jacuzzi

    A modern bathroom with a marble wall, a black speaker, and a glass shower enclosure.

    6. Casa Vacanze Le Case

    A stone building with a pool and outdoor seating, surrounded by greenery and a view of distant mountains.

    7. 7 min from Cantina Antinori in Chianti Classico | Pool | Casa Sala & Pepe

    A rustic stone building with a large arched doorway, surrounded by lush greenery and a cobblestone path.

    8. Ebbio – Villa and Organic Farm in Monteriggioni

    A rustic villa with a garden, a pond, and a mountainous backdrop.

    9. Farmhouse in Chianti

    A pool area with lounge chairs and a table, surrounded by greenery and lavender plants.

    10. Casa San Martino between Florence and Siena with Pool

    A swimming pool with a clear blue sky and trees in the background.

    11. Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi

    A rectangular swimming pool with a metal fence, surrounded by trees and a clear sky.

    12. Apartment House with garden Tuscany Chianti , Florence 15km.

    A swimming pool with clear blue water, surrounded by trees and a wooden deck.

    13. country house with garden ,pool,children's play area ,Tuscany,15 from Florence

    An outdoor patio with a table, chairs, and a view of a landscape.

    14. Comfortable double room with a bathroom in the historic center of San Gimignano.

    Room

    15. Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC

    Pool

    16. Deluxe Room - A comfortable and elegant room in the heart of San Gimignano.

    A hotel room with a bed, a bedside table with a lamp, and two framed abstract paintings on the wall.

    17. IL TOLOMEI - new apartment in the middle of the main street

    A narrow street with stone buildings, a person walking, and a clear blue sky.

    18. Villa La Stella - Casa per Ferie

    A large, multi-story building surrounded by lush greenery and trees.

    19. A cozy, Tuscan-style apartment perfect for families. Pets Allowed

    A rustic building with a brick facade, a small arched window, and a door.

    20. Holiday Home 'Chianti Summer' with Pool, Garden and Wi-Fi

    A dining area with a table and chairs, a sofa, and large windows with curtains.

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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    Learn more about Castellina in Chianti

    Medieval stone buildings line the narrow streets where you'll find Tuscany's best wine shops and the fascinating Etruscan tomb museum. Climb the fortress tower for panoramic vineyard views, then join locals at Piazza del Comune for aperitivo hour with regional cheeses.

    See all hotels in Castellina in Chianti

    A stone building with a clock tower, steps leading up to it, and people walking around.