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A historic castle on a hill with surrounding greenery and buildings.

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    Check prices for these dates

    Check prices for these dates, 15 – 16 December 2026

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    Our top choices for Montalcino holiday homes

    1. Podere Belsogno-camera Lavanda

    A pergola with a table and chairs overlooking a vineyard and distant hills.

    2. A Casetta di Brunello, tranquil and with breathtaking views.

    A stone building with a wooden door and two windows with shutters.

    3. Il Borghetto - The House on Elba, Rooftop Terrace with Panoramic Views

    A terrace with a table set for dining, surrounded by brick walls and overlooking a scenic landscape.

    4. A typical Tuscan country house

    A pathway leading to a building with stone walls and a tree.

    5. Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center

    A narrow stone corridor with a vaulted ceiling, leading to a room with a long table and chairs.

    6. Podere Giardino Wine & Bed – Glicine Apartment: Country House with Pool, Wi-Fi & AC

    A swimming pool surrounded by lush greenery and trees, with lounge chairs and umbrellas.

    7. Charming Siena Countryside Stay

    A patio area with a gravel floor, potted plants, and a white umbrella.

    8. Exclusive Stone Tower.

    A stone building with two windows and a door, surrounded by a small garden with a rose bush.

    9. Tuscan House: Spacious Traditional Apartment with a Large Outdoor Area and Breakfast Included

    A stone wall with a wooden door, a paved pathway, and green shrubbery.

    10. Vacation in Poggettone

    A small brick structure with an arched entrance, surrounded by gravel, potted plants, and trees.

    11. Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza

    A bedroom with a wooden headboard, two bedside tables with lamps, a bed with a quilted cover, and two vases of flowers.

    12. Romantic farmhouse in the Sienese hills

    A narrow stone pathway leading through an old stone building with arched doorways and potted plants.

    13. Holiday Home 'La Nobiltà Del Tempo' with Balcony and Wi-Fi

    A narrow stone staircase leading to a door with a glass panel, flanked by brick walls and metal railings.

    14. Renovated Tuscan-style country house

    A swimming pool with metal ladders, surrounded by trees and a stone wall, reflecting the sky.

    15. Double room with private bathroom in the countryside, 5 minutes from Montepulciano

    A neatly made bed with a dark patterned bedspread, two bedside tables with lamps, and two framed pictures on the wall.

    16. Detached house with a garden, just a few minutes from the Abbey of San Galgano

    A patio with a wooden table, a blue lounge chair, a striped chair, and a large umbrella.

    17. A peaceful spot with a garden between Chianti and Crete, near the old town

    A modern kitchen with a glass dining table, dark cabinetry, and a view through an open door.

    18. Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

    A rustic brick building with a mural, a clock, and various potted plants.

    19. Vacation home with a panoramic terrace, ideal for families and couples

    A house number 102, a security keypad, and a plaque with a floral design.

    20. "Edera" Apartment in Agriturismo with Shared Pool, Mountain View, and Wi-Fi

    A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas.

    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 Montalcino

    Medieval stone walls surround this hilltop town where Brunello wine tastings await in historic cellars beneath the fortress. Climb the Torre del Palazzo Comunale for valley views, then sample local pecorino cheese and honey at shops along the narrow lanes.

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    A historic castle on a hill with surrounding greenery and buildings.