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Search results; Over 1,000 homes in Castellina in Chianti

Guest favourite
Apartment in Castellina in Chianti
Farmhouse with pool Godenano Di Mezzo
2 bedrooms, 3 beds, 2 private bathrooms
29 Sept – 4 Oct, Individual host
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4.83 out of 5 average rating, 29 reviews
Top guest favourite
Barn in Castellina in Chianti
Cipressini 1 - Swimming pool and stunning view
Individual host
2–7 Nov
5.0 out of 5 average rating, 98 reviews
Top guest favourite
Home in Castellina in Chianti
Apartment with stunning view on the vineyards
Business host
25–30 Oct
4.97 out of 5 average rating, 33 reviews
Top guest favourite
Villa in Barberino Tavarnelle
Luxury Villa in Chianti • Private Natural Pool
Individual host
2–7 Oct
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Flat in Castellina in Chianti
Casa Mirella in Chianti
Individual host
26–31 Oct
4.95 out of 5 average rating, 56 reviews
Top guest favourite
Villa in Radda in Chianti
Villa with pool in Chianti - Castellare Petroso
Business host
3–8 Oct
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Townhouse in Colle di Val d'Elsa
Il Cristallo – Dream Getaway in Tuscany
Business host
9–14 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Poggibonsi
Relax in Chianti countryside
Individual host
17–22 Oct
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Home in Monteriggioni
Beautiful Villa with private swimming pool
Individual host
10–17 Oct
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
Individual host
29 Oct – 3 Nov
4.98 out of 5 average rating, 85 reviews
Top guest favourite
Villa in Poggibonsi
Wonderful villa for 6 with heatable swimming pool
Individual host
31 Oct – 7 Nov
5.0 out of 5 average rating, 19 reviews
Flat in Poggibonsi
Refined Comfort Apartment Villa in Vineyard for 7
Business host
9–14 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Barberino Tavarnelle
Podere Le Casette Garden
Business host
10–15 Sept
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Poggibonsi
Il Greppo rustic charm Tuscan views & Hot Tub
Individual host
2–7 Nov
5.0 out of 5 average rating, 27 reviews
Superhost
Home in Figline e Incisa Valdarno
Villa among our vineyards on the outskirts of Chianti
Business host
9–14 Sept
New place to stay
Guest favourite
Farm stay in Poggibonsi
Holiday home Poggio al olive trees
Business host
16–21 Oct
5.0 out of 5 average rating, 32 reviews
Cottage in Castellina in Chianti
Cottage with a view on Chianti hills
Individual host
19–26 Sept
4.69 out of 5 average rating, 16 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Top guest favourite
Villa in Gaiole in Chianti
Montemarcoli
Individual host
7–14 Nov
5.0 out of 5 average rating, 34 reviews