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Homes in Castellina in Chianti
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Search results; Over 1,000 homes in Castellina in Chianti
Over 1,000 homes in Castellina in Chianti
Guest favourite
Guest favourite
Flat in Castellina in Chianti
Apartment T4
2 bedrooms
,
·
2 beds
,
·
2 private bathrooms
28 Oct – 2 Nov
28 Oct – 2 Nov
$1,650 SGD
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for 5 nights
$1,650 SGD for 5 nights
,
·
4.87 out of 5 average rating, 75 reviews
4.87 (75)
Top guest favourite
Guest favourite
Flat in Castellina in Chianti
Casa Mirella in Chianti
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
25–30 Oct
25–30 Oct
$861 SGD
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for 5 nights
$861 SGD for 5 nights
Extended stay discount
4.95 out of 5 average rating, 56 reviews
4.95 (56)
Top guest favourite
Guest favourite
Barn in Castellina in Chianti
Cipressini 1 - Swimming pool and stunning view
1 bedroom
1 bedroom
,
·
3 beds
3 beds
2–7 Nov
2–7 Nov
$2,334 SGD
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for 5 nights
$2,334 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 97 reviews
5.0 (97)
Top guest favourite
Guest favourite
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
29 Oct – 3 Nov
29 Oct – 3 Nov
$1,389 SGD
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for 5 nights
$1,389 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 84 reviews
4.98 (84)
Top guest favourite
Guest favourite
Farm stay in Castellina in Chianti
1st floor apartment with shared pool - 4 pax
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
18–23 Oct
18–23 Oct
$1,774 SGD
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for 5 nights
$1,774 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 15 reviews
5.0 (15)
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
15–20 Sept
15–20 Sept
$5,145 SGD
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for 5 nights
$5,145 SGD for 5 nights
New place to stay
New
Superhost
Superhost
Home in Castellina in Chianti
Cinderella Chianti - House
6 bedrooms
6 bedrooms
,
·
8 beds
8 beds
4–9 Oct
4–9 Oct
$5,542 SGD
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for 5 nights
$5,542 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Home in Castellina in Chianti
Apartment with stunning view on the vineyards
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
25–30 Oct
25–30 Oct
$1,105 SGD
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for 5 nights
$1,105 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 31 reviews
4.97 (31)
Top guest favourite
Guest favourite
Home in Poggibonsi
Relax in Chianti countryside
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
3–8 Sept
3–8 Sept
$2,162 SGD
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for 5 nights
$2,162 SGD for 5 nights
5.0 out of 5 average rating, 38 reviews
5.0 (38)
Top guest favourite
Guest favourite
Home in Poggibonsi
Il Greppo rustic charm Tuscan views & Hot Tub
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
2–7 Nov
2–7 Nov
$1,149 SGD
$1,027 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 27 reviews
5.0 (27)
Holiday home in Barberino Tavarnelle
Le Querciole by Mauro Corsi
4 bedrooms
4 bedrooms
,
·
3 double beds
3 double beds
3–8 Sept
3–8 Sept
$4,341 SGD
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for 5 nights
$4,341 SGD for 5 nights
Home in Castellina in Chianti
Cignanbianco - Sunrise and Sunset by Interhome
5 bedrooms
5 bedrooms
,
·
3 single beds
3 single beds
15–22 Oct
15–22 Oct
$1,635 SGD
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for 7 nights
$1,635 SGD for 7 nights
Free cancellation
4.75 out of 5 average rating, 4 reviews
4.75 (4)
Top guest favourite
Guest favourite
Loft in Castellina in Chianti
Palazzo Bianciardi - Penthouse
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
19–24 Oct
19–24 Oct
$884 SGD
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for 5 nights
$884 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 19 reviews
5.0 (19)
Top guest favourite
Guest favourite
Home in Lecchi
"La Casa di Maria Luce"® with panoramic terrace
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
16–21 Sept
16–21 Sept
$999 SGD
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for 5 nights
$999 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 244 reviews
4.96 (244)
Top guest favourite
Guest favourite
Townhouse in Colle di Val d'Elsa
Il Cristallo – Dream Getaway in Tuscany
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
6–11 Sept
6–11 Sept
$3,670 SGD
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for 5 nights
$3,670 SGD for 5 nights
5.0 out of 5 average rating, 9 reviews
5.0 (9)
Home in Castellina in Chianti
3 bedroom stone house on olive grove
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
6–11 Sept
6–11 Sept
$4,081 SGD
$3,404 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Guest favourite
Guest favourite
Flat in Panzano in Chianti
Alessandro's apartment
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
4–9 Sept
4–9 Sept
$670 SGD
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for 5 nights
$670 SGD for 5 nights
5.0 out of 5 average rating, 11 reviews
5.0 (11)
Top guest favourite
Guest favourite
Villa in Radda in Chianti
Tuscan character, contemporary style and comfort
5 bedrooms
5 bedrooms
,
·
5 king beds
5 king beds
26–31 Oct
26–31 Oct
$9,810 SGD
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for 5 nights
$9,810 SGD for 5 nights
4.99 out of 5 average rating, 69 reviews
4.99 (69)
Flat in Certaldo
La Casa di Mario: Apt near Siena and Florence
3 bedrooms
3 bedrooms
,
·
3 double beds
3 double beds
29 Sept – 4 Oct
29 Sept – 4 Oct
$1,066 SGD
$958 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 4 reviews
5.0 (4)
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