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Search results; Over 1,000 homes in Monteriggioni

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Top guest favourite
Barn in Monteriggioni
Charming Barn with Pool - Chianti Area
2 bedrooms, 3 beds, 1 private bathroom
10–15 Oct
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4.98 out of 5 average rating, 65 reviews
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Top guest favourite
Home in Monteriggioni
Beautiful Villa with private swimming pool
2 bedrooms, 3 beds, 2 bathrooms
10–17 Oct
5.0 out of 5 average rating, 18 reviews
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Guest favourite
Room in Monteriggioni
Rooms and Wine Monteriggioni, Il chianti
1 double bed, 1 bathroom
3–8 Nov
5.0 out of 5 average rating, 42 reviews
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Home in Monteriggioni
Below the Monteriggioni Walls
2 bedrooms, 3 beds, 2 bathrooms
4–9 Oct
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Guest favourite
Home in Monteriggioni
The Barn Detached house surrounded by greenery
1 bedroom, 2 beds, 1 bathroom
16–21 Oct
5.0 out of 5 average rating, 15 reviews
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Top guest favourite
Flat in Poggibonsi
Casal De' Matti - Margot House
2 bedrooms, 3 beds, 2 bathrooms
26–31 Oct
4.98 out of 5 average rating, 47 reviews
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Top guest favourite
Villa in Monteriggioni
Tenuta Uzielli an elegant countryside villa
7 bedrooms, 7 beds, 8 bathrooms
1–6 May
5.0 out of 5 average rating, 20 reviews
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Top guest favourite
Home in Castellina in Chianti
Capanna di Sotto by Interhome.
2 bedrooms, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Flat in Gavignano
Poggio Massiccioli
2 bedrooms, 2 queen beds, 1 bathroom
30 Oct – 4 Nov
4.92 out of 5 average rating, 390 reviews
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Guest favourite
Flat in Staggia
The Optimist's House
1 bedroom, 1 bed, 1 bathroom
9–14 Oct
4.9 out of 5 average rating, 71 reviews
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Top guest favourite
Flat in Monteriggioni
Osea Agritourism, Alba apartment
2 bedrooms, 4 beds, 1 bathroom
8–13 Oct
5.0 out of 5 average rating, 49 reviews
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Guest favourite
Home in Monteriggioni
Next to castle of Villa-Siena. heart Francigena
4 bedrooms, 8 beds, 2 bathrooms
10–15 Oct
4.84 out of 5 average rating, 158 reviews
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Top guest favourite
Home in Castellina in Chianti
Apartment with stunning view on the vineyards
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.97 out of 5 average rating, 33 reviews
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Top guest favourite
Flat in Poggibonsi
Laura Chianti Holidays
2 bedrooms, 5 beds, 2 bathrooms
22–27 Nov
4.98 out of 5 average rating, 342 reviews
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Guest favourite
Home in Monteriggioni
Romantic panoramic farmhouse near Siena
1 bedroom, 1 double bed, 1 bathroom
21–26 Oct
4.92 out of 5 average rating, 39 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
7–12 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Poggiolo
Country House Podere l 'Assunta
2 bedrooms, 4 beds, 1 bathroom
27 Oct – 1 Nov
5.0 out of 5 average rating, 92 reviews
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Top guest favourite
Room in San Gimignano
Maggie's Million Dollar View Lodge - S. Gimignano
1 double bed, 1 bathroom
9–14 Oct
4.94 out of 5 average rating, 176 reviews
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Top guest favourite
Flat in Poggibonsi
App. Poggiarello
2 bedrooms, 3 beds, 2 bathrooms
11–16 Oct
4.96 out of 5 average rating, 57 reviews