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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
Apartment in a detached villa - Val d'Orcia
4.95 out of 5 average rating, 173 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
Villa in Pienza
Unplug at a 17th-Century Farmhouse Enveloped by Olive Groves
4.99 out of 5 average rating, 109 reviews, 2 bedrooms, 3 beds, 1 bathroom
22–27 Aug
Flat in Castiglione d'Orcia
Stone house overlooking Piazza Vecchietta
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 3 beds, 1 bathroom
17–22 Jul
Top guest favourite
Farm stay in San Quirico d'Orcia
Vineyards and Val d’Orcia views from balconies
4.98 out of 5 average rating, 115 reviews, 5 bedrooms, 5 beds, 5.5 bathrooms
20–25 Jul
Top guest favourite
Flat in Castiglione d'Orcia
Farmhouse with panoramic terrace in Val d’Orcia
4.96 out of 5 average rating, 75 reviews, 2 bedrooms, 4 beds, 1 bathroom
15–20 Aug
Top guest favourite
Farm stay in San Quirico d'Orcia
Val d’Orcia views with free wine tasting
4.96 out of 5 average rating, 113 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Jul – 4 Aug
Top guest favourite
Place to stay in Castiglione d'Orcia
Meadow farmhouse deep in Val d’Orcia woods
4.97 out of 5 average rating, 63 reviews, 1 bedroom, 1 bed, 1 bathroom
17–22 Jul
Home in Castelnuovo dell'Abate
Private gazebo facing the Tuscan hills
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 3 beds, 3 bathrooms
25–30 Jul
Top guest favourite
Farm stay in Seggiano
Terra Delle Sidhe, Seggiano, Tuscany, Italy
4.99 out of 5 average rating, 283 reviews, 2 bedrooms, 4 beds, 1 bathroom
31 Aug – 5 Sept
Top guest favourite
Flat in Castiglione d'Orcia
Geraneo apartment in Valdorcia
5.0 out of 5 average rating, 13 reviews, 1 bedroom, 1 bed, 1 bathroom
8–13 Oct
Top guest favourite
Flat in San Quirico d'Orcia
Apartment in Val d'Orcia
5.0 out of 5 average rating, 39 reviews, 2 bedrooms, 3 beds, 2 bathrooms
3–8 Aug
Superhost
Flat in Montalcino
Wp Relais Argante Apartment
3 bedrooms, 4 beds, 3 bathrooms
23–28 Jul
Home in Castiglione d'Orcia
Il Gugnolo - Farmhouse in Val d'Orcia
4.75 out of 5 average rating, 4 reviews, 4 bedrooms, 6 beds, 3 bathrooms
16–21 Jul
Guest favourite
Villa in Poggioferro
Poggio among the olive trees
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
Guest favourite
Home in Pienza
Spacious Luxury Stay in Pienza | 3BR 3BA
4.98 out of 5 average rating, 91 reviews, 3 bedrooms, 3 beds, 3 bathrooms
16–21 Aug
Guest favourite
Home in Pienza
Casa di Vico, just a short walk from the center of Pienza
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 1 bed, 3 bathrooms
26–31 Jul