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

Descriptions are based on details hosts provide
Guest favourite
Apartment in Castiglione d'Orcia
Ermione
1 bedroom, 3 beds, 1 private bathroom
26–31 Jul
,
4.92 out of 5 average rating, 212 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
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
Home in Castiglione d'Orcia
Il Gugnolo - Farmhouse in Val d'Orcia
4 bedrooms, 6 beds, 3 bathrooms
16–21 Jul
4.75 out of 5 average rating, 4 reviews
Flat in Castiglione d'Orcia
Casa Aldobrandesca
2 bedrooms, 2 queen beds, 1 bathroom
17–22 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Castiglione d'Orcia
Farmhouse with panoramic terrace in Val d’Orcia
2 bedrooms, 4 beds, 1 bathroom
15–20 Aug
4.96 out of 5 average rating, 75 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
Home in Castelnuovo dell'Abate
Modern Home near Montalcino with Private Garden
3 bedrooms, 3 double beds, 3 bathrooms
25–30 Jul
5.0 out of 5 average rating, 3 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
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
Villa in Chianciano Terme
Hot tub with a view in Tuscany
2 bedrooms, 4 beds, 2 bathrooms
15–20 Jul
4.97 out of 5 average rating, 126 reviews
Top guest favourite
Farm stay in Bagno Vignoni
The garden of the oaks (Podere Santa Caterina)
4 bedrooms, 5 beds, 2 bathrooms
15–20 Jul
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Place to stay in Castiglione d'Orcia
Meadow farmhouse deep in Val d’Orcia woods
1 bedroom, 1 double bed, 1 bathroom
17–22 Jul
4.97 out of 5 average rating, 63 reviews
Guest favourite
Flat in Montepulciano
Wine-inspired retreat near the historic center
2 bedrooms, 2 beds, 1 bathroom
2–7 Sept
4.87 out of 5 average rating, 15 reviews
Top guest favourite
Apartment in Torrenieri
[9 minutes from Montalcino] Elegant House Mafalda
2 bedrooms, 4 beds, 1 bathroom
29 Jul – 3 Aug
4.97 out of 5 average rating, 308 reviews
Top guest favourite
Apartment in San Quirico d'Orcia
Panoramic views in Val d’Orcia’s heart
2 bedrooms, 2 double beds, 1 bathroom
17–22 Jul
4.99 out of 5 average rating, 96 reviews
Top guest favourite
Farm stay in Pienza
Hilltop farmstay with Val d’Orcia views
3 bedrooms, 4 beds, 3 bathrooms
15–20 Jul
4.97 out of 5 average rating, 34 reviews
Top guest favourite
Home in Castiglione d'Orcia
Val d’Orcia views from a panoramic garden
1 bedroom, 2 beds, 1 bathroom
16–21 Oct
4.96 out of 5 average rating, 129 reviews
Top guest favourite
Apartment in San Quirico d'Orcia
Modern apartment in the Val d’Orcia
2 bedrooms, 2 beds, 1 bathroom
29 Aug – 3 Sept
4.98 out of 5 average rating, 50 reviews