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

Descriptions are based on details hosts provide
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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
4.95 out of 5 average rating, 174 reviews, 2 bedrooms, 2 beds, 1 bathroom
13–18 Aug
Top guest favourite
Home in Castiglione d'Orcia
Stone house renovated in 2025, Val d’Orcia
5.0 out of 5 average rating, 25 reviews, 3 bedrooms, 4 beds, 3.5 bathrooms
26–31 Jul
Top guest favourite
Farm stay in San Quirico d'Orcia
Podere Pereti Nuovi – Modern Tuscan Villa
4.98 out of 5 average rating, 115 reviews, 5 bedrooms, 5 beds, 5.5 bathrooms
20–25 Jul
Top guest favourite
Home in Castiglione d'Orcia
Da nonna Ornella - nest in Val d'Orcia
4.96 out of 5 average rating, 129 reviews, 1 bedroom, 2 beds, 1 bathroom
16–21 Oct
Top guest favourite
Farm stay in Pienza
Medieval castle with exposed beams and pool
4.97 out of 5 average rating, 177 reviews, 1 bedroom, 1 bed, 1 bathroom
25–30 Mar
Top guest favourite
Flat in Monticchiello
Casa Bonari - a paradise for the eyes
4.97 out of 5 average rating, 183 reviews, 3 bedrooms, 4 beds, 2 bathrooms
26 Sept – 1 Oct
Top guest favourite
Villa in Castiglione d'Orcia
46-hectare estate in Val d’Orcia
5.0 out of 5 average rating, 21 reviews, 11 bedrooms, 10 beds, 11 bathrooms
17–22 Oct
Top guest favourite
Farm stay in Monticchiello
Val d’Orcia views and a travertine pool
4.99 out of 5 average rating, 67 reviews, 4 bedrooms, 4 beds, 4 bathrooms
30 Oct – 4 Nov
Guest favourite
Villa in Poggioferro
Pool with stunning views among olive groves
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 3 beds, 2 bathrooms
6–11 Oct
Top guest favourite
Farm stay in Montalcino
Tuscan Farmhouse ~ Magic Sunsets ~ 360° view
4.98 out of 5 average rating, 43 reviews, 2 bedrooms, 3 beds, 2 bathrooms
31 Jul – 5 Aug
Top guest favourite
Apartment in Pienza
A 1500s barn on an organic farm
5.0 out of 5 average rating, 154 reviews, 2 bedrooms, 2 beds, 2 bathrooms
19–24 Oct
Top guest favourite
Flat in Castiglione d'Orcia
farmhouse for families with children in val d'orcia
4.96 out of 5 average rating, 75 reviews, 2 bedrooms, 4 beds, 1 bathroom
15–20 Aug
Flat in Castiglione d'Orcia
Casa Aldobrandesca
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 3 beds, 1 bathroom
17–22 Jul
Top guest favourite
Tower in San Quirico d'Orcia
A 1000-year-old tower overlooking Val d’Orcia
5.0 out of 5 average rating, 113 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Aug
Top guest favourite
Villa in Pienza
17th-century farmhouse amid olive groves
4.99 out of 5 average rating, 109 reviews, 2 bedrooms, 3 beds, 1 bathroom
22–27 Aug
Top guest favourite
Flat in Pienza
Historic 1400s building near the Duomo
4.98 out of 5 average rating, 44 reviews, 3 bedrooms, 4 beds, 2 bathrooms
13–18 Aug
Top guest favourite
Home in Montalcino
Domus Antiqua
4.95 out of 5 average rating, 40 reviews, 3 bedrooms, 3 beds, 2 bathrooms
25–30 Jul
Top guest favourite
Apartment in Montepulciano
The walnut tree view, Montepulciano
5.0 out of 5 average rating, 121 reviews, 1 bedroom, 1 bed, 1 bathroom
31 Oct – 5 Nov