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

Descriptions are based on details hosts provide
Guest favourite
Farm stay in Gaiole in Chianti
Il Nido - a romantic hearth
1 bedroom, 1 bed, 1 private bathroom
25–30 Oct
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4.94 out of 5 average rating, 257 reviews
Guest favourite
Villa in Gaiole in Chianti
Villa Il Masseto
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 3 beds, 3 bathrooms
26–31 Jul
Top guest favourite
Villa in Gaiole in Chianti
Wine estate villa in Chianti Classico
5.0 out of 5 average rating, 25 reviews, 5 bedrooms, 5 beds, 5 bathrooms
28 Jul – 2 Aug
Top guest favourite
Villa in Gaiole in Chianti
Pool, spa, and vineyard in Chianti
4.99 out of 5 average rating, 69 reviews, 4 bedrooms, 4 beds, 4 bathrooms
24–31 Oct
Guest favourite
Home in Radda in Chianti
Villa le Scope 5*
4.98 out of 5 average rating, 45 reviews, 3 bedrooms, 4 beds, 3 bathrooms
28 Jul – 2 Aug
Flat in Gaiole in Chianti
Mill in Chianti - Rosa
1 bedroom, 2 beds, 1 bathroom
8–13 Aug
Guest favourite
Flat in Cavriglia
Apartment Comfort | Quiet Escape in Tuscany
5.0 out of 5 average rating, 15 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Aug
Guest favourite
Home in Gaiole in Chianti
House in the heart of Chianti
4.95 out of 5 average rating, 21 reviews, 2 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
Luxe
Home in Gaiole in Chianti
La Tuscia – Tuscan Estate, Boutique Villa
5.0 out of 5 average rating, 22 reviews, 4 bedrooms, 4 beds, 5 bathrooms
15–20 Aug
Home in Gaiole in Chianti
Stone farmhouse with pool amid vineyards
4.67 out of 5 average rating, 18 reviews, 6 bedrooms, 11 beds, 4 bathrooms
28 Jul – 2 Aug
Superhost
Flat in Bossi
Villino Ersilia Music, the charm of Chianti
2 bedrooms, 3 beds, 2 bathrooms
25–30 Jul
Guest favourite
Villa in Gaiole in Chianti
Secluded Chianti villa with 180-degree views
5.0 out of 5 average rating, 30 reviews, 3 bedrooms, 4 beds, 3 bathrooms
29 Aug – 3 Sept
Top guest favourite
Villa in Gaiole in Chianti
Stone cottage with castle views in Chianti
4.93 out of 5 average rating, 44 reviews, 2 bedrooms, 2 beds, 2 bathrooms
31 Oct – 7 Nov
Guest favourite
Home in Gaiole in Chianti
Montelucci Chianti Agrivilla
5.0 out of 5 average rating, 7 reviews, 7 bedrooms, 11 beds, 6 bathrooms
18–23 Oct
Top guest favourite
Home in Lecchi
13th-century stone house with panoramic terrace
4.96 out of 5 average rating, 240 reviews, 2 bedrooms, 4 beds, 2 bathrooms
24–29 Jul
Flat in Gaiole in Chianti
Podere L'Aquila- Lavanda
3 bedrooms, 4 beds, 1 bathroom
6–11 Oct
Top guest favourite
Flat in Cavriglia
Modern flat in a medieval Chianti village
4.97 out of 5 average rating, 156 reviews, 2 bedrooms, 3 beds, 1 bathroom
26–31 Jul
Superhost
Holiday home in Montegonzi
Vino apartment 70 m2 view swimming pool
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 4 beds, 1 bathroom
28 Aug – 2 Sept
Top guest favourite
Flat in Castellina in Chianti
Casa Mirella in Chianti
4.94 out of 5 average rating, 53 reviews, 2 bedrooms, 2 beds, 1 bathroom
25–30 Jul