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A medieval castle surrounded by a moat and dense greenery.

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    Check prices for these dates

    Check prices for these dates, 14 – 15 December 2026

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    Our top choices for Castiglione del Lago holiday homes

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

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

    2. Holiday Home 'Il Forcone' with Shared Pool, Wi-Fi and Air Conditioning

    An outdoor seating area with tables and chairs, surrounded by palm trees and a view of the sea.

    3. Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi

    A stone archway leading to a building with a tiled roof, surrounded by gravel and potted plants.

    4. Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi

    A stone building with a balcony, an archway, and potted plants.

    5. Holiday Home in Villa Pandolfina near Montepulciano

    A covered patio with a brick wall, a round table with chairs, and a view of greenery.

    6. 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.

    7. Montecchio di Cortona

    Property grounds

    8. Eagle House

    A swimming pool with lounge chairs, a stone building, and a garden with various plants and a large terracotta pot.

    9. Villa on the Umbria-Tuscany border—for families and friends—with a private pool

    An aerial view of a property with a main house, a swimming pool, and terraced gardens.

    10. The Rose Cottage - Vacation Home with a Garden in Umbria

    A backyard with a paved walkway, a brick wall, a large flower pot, and a variety of plants and trees.

    11. Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning

    A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a clear blue sky.

    12. La Perla del Lago Vacation Home - All the comforts of home with a view of the lake!

    A dining table set outdoors with a view of the sunset over a body of water.

    13. 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.

    14. Exclusive Private Villa for Groups with Panoramic Pool and Large Common Room – Between Tuscany and Umbria

    A swimming pool with a gazebo, lounge chairs, and a view of the mountains.

    15. Apartment 'Pugnano Alto – Castagna' with Panoramic View and Pool – 2 Bedrooms with Private Bathroom

    A rectangular swimming pool with a stone deck, surrounded by grass and trees, with a view of distant hills.

    16. Apartment "Pugnano Alto - Tartufo" with Shared Pool and Wi-Fi

    A rectangular swimming pool with a stone deck, surrounded by grass and trees, with a view of distant hills.

    17. Apartment 'Pugnano Alto- Girasole' with Shared Pool, Private Terrace and Wi-Fi

    A stone building with a glass table and chairs, outdoor seating, and a staircase leading to an upper level.

    18. Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning

    A brick building with a large sliding glass door, a brown door, and a small potted plant.

    19. Country House Le Case Coloniche

    A swimming pool with lounge chairs and umbrellas, a stone building with arches, and a large tree in the background.

    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 Castiglione del Lago

    Medieval towers and fortress walls frame spectacular views of Lake Trasimeno from this hilltop town. Explore Palazzo della Corgna's Renaissance frescoes, then enjoy local wine at lakeside restaurants as fishing boats return at sunset.

    See all hotels in Castiglione del Lago

    A medieval castle surrounded by a moat and dense greenery.