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Search results; Over 1,000 homes in Castiglione d'Orcia

Descriptions are based on details hosts provide
Guest favourite
Villa in Castiglione d'Orcia
Wp Relais Villa Vignalunga
4 bedrooms, 4 beds, 4.5 private bathrooms
18–23 Aug
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4.93 out of 5 average rating, 116 reviews
Top guest favourite
Home in Castiglione d'Orcia
Tuscan terrace with sunset views over Montalcino
2 bedrooms, 2 queen beds, 1 bathroom
13–18 Aug
4.95 out of 5 average rating, 174 reviews
Top guest favourite
Farm stay in San Quirico d'Orcia
Vineyards and Val d’Orcia views from balconies
5 bedrooms, 5 double beds, 5.5 bathrooms
20–25 Jul
4.98 out of 5 average rating, 115 reviews
Top guest favourite
Home in Castiglione d'Orcia
Stone house renovated in 2025, Val d’Orcia
3 bedrooms, 4 beds, 3.5 bathrooms
26–31 Jul
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Farm stay in Pienza
Medieval castle with exposed beams and pool
1 bedroom, 1 queen bed, 1 bathroom
25–30 Mar
4.97 out of 5 average rating, 177 reviews
Top guest favourite
Flat in Monticchiello
Casa Bonari - a paradise for the eyes
3 bedrooms, 4 beds, 2 bathrooms
26 Sept – 1 Oct
4.97 out of 5 average rating, 183 reviews
Top guest favourite
Home in Castiglione d'Orcia
Da nonna Ornella - nest in Val d'Orcia
1 bedroom, 2 beds, 1 bathroom
16–21 Oct
4.96 out of 5 average rating, 129 reviews
Top guest favourite
Villa in Castiglione d'Orcia
46-hectare estate in Val d’Orcia
11 bedrooms, 10 king beds, 11 bathrooms
17–22 Oct
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Farm stay in Monticchiello
Podere Lamino, Val d'Orcia, Pienza
4 bedrooms, 4 queen beds, 4 bathrooms
30 Oct – 4 Nov
4.99 out of 5 average rating, 67 reviews
Guest favourite
Villa in Poggioferro
Poggio among the olive trees
4 bedrooms, 3 beds, 2 bathrooms
6–11 Oct
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Farm stay in Montalcino
Tuscan Farmhouse ~ Magic Sunsets ~ 360° view
2 bedrooms, 3 beds, 2 bathrooms
31 Jul – 5 Aug
4.98 out of 5 average rating, 43 reviews
Top guest favourite
Apartment in Pienza
Mascagni Farmhouse in Val d'Orcia, Pienza
2 bedrooms, 2 double beds, 2 bathrooms
19–24 Oct
5.0 out of 5 average rating, 154 reviews
Top guest favourite
Flat in Castiglione d'Orcia
farmhouse for families with children in val d'orcia
2 bedrooms, 4 beds, 1 bathroom
15–20 Aug
4.96 out of 5 average rating, 75 reviews
Flat in Castiglione d'Orcia
Stone house overlooking Piazza Vecchietta
2 bedrooms, 2 queen beds, 1 bathroom
17–22 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Tower in San Quirico d'Orcia
A 1000-year-old tower overlooking Val d’Orcia
1 bedroom, 1 king bed, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 113 reviews
Top guest favourite
Apartment in Montepulciano
Hilltop terrace with Val d’Orcia views
1 bedroom, 1 double bed, 1 bathroom
31 Oct – 5 Nov
5.0 out of 5 average rating, 121 reviews
Top guest favourite
Flat in Pienza
Historic 1400s building near the Duomo
3 bedrooms, 4 beds, 2 bathrooms
13–18 Aug
4.98 out of 5 average rating, 44 reviews
Top guest favourite
Villa in Pienza
17th-century farmhouse amid olive groves
2 bedrooms, 3 beds, 1 bathroom
22–27 Aug
4.99 out of 5 average rating, 109 reviews
Top guest favourite
Home in Montalcino
Terrace with countryside views in Montalcino
3 bedrooms, 3 beds, 2 bathrooms
25–30 Jul
4.95 out of 5 average rating, 40 reviews