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

Descriptions are based on details hosts provide
Superhost
Cottage in Gaiole in Chianti
Old Chianti chapel-style cottage
2 bedrooms, 2 beds, 1 private bathroom
21–28 Aug
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4.84 out of 5 average rating, 131 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
Home in Lecchi
"La Casa di Maria Luce"® with panoramic terrace
4.96 out of 5 average rating, 240 reviews, 2 bedrooms, 4 beds, 2 bathrooms
24–29 Jul
Superhost
Flat in Bossi
Restored barn in vineyards with a fireplace
2 bedrooms, 3 beds, 2 bathrooms
25–30 Jul
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
Guest favourite
Home in Radda in Chianti
Renovated farmhouse with fireplaces in Chianti
4.98 out of 5 average rating, 45 reviews, 3 bedrooms, 4 beds, 3 bathrooms
28 Jul – 2 Aug
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
Flat in Gaiole in Chianti
200-year-old home with valley views
3 bedrooms, 4 beds, 1 bathroom
6–11 Oct
Flat in Gaiole in Chianti
Podere L'Aquila- Agapanto
3 bedrooms, 4 beds, 2 bathrooms
27 Jul – 1 Aug
Flat in Gaiole in Chianti
Mill in Chianti - Rosa
1 bedroom, 2 beds, 1 bathroom
8–13 Aug
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
Sestuccia
4.99 out of 5 average rating, 69 reviews, 4 bedrooms, 4 beds, 4 bathrooms
24–31 Oct
Top guest favourite
Villa in Radda in Chianti
Tuscan character, contemporary style and comfort
4.98 out of 5 average rating, 64 reviews, 5 bedrooms, 5 beds, 5 bathrooms
26–31 Oct
Top guest favourite
Apartment in Cavriglia
Chianti La Pruneta, Michelangelo apartment.
4.89 out of 5 average rating, 180 reviews, 1 bedroom, 3 beds, 1 bathroom
15–20 Jul
Superhost
Villa in Radda in Chianti
Vineyard views and a pool in Chianti
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 4 beds, 4 bathrooms
22–27 Aug
Guest favourite
Farm stay in Gaiole in Chianti
Le Miccine Villa in Tuscany for 6 w/ Pool
4.92 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 3 bathrooms
24–29 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
Top guest favourite
Flat in San Gusmè
Beautiful medieval village!!!
4.99 out of 5 average rating, 460 reviews, 2 bedrooms, 2 beds, 2 bathrooms
26–31 Oct
Top guest favourite
Flat in San Gusmè
La Dimora del Luca
4.99 out of 5 average rating, 160 reviews, 1 bedroom, 2 beds, 1 bathroom
23–28 Aug