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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
3 bedrooms, 3 double beds, 3 bathrooms
26–31 Jul
5.0 out of 5 average rating, 5 reviews
Luxe
Home in Gaiole in Chianti
La Tuscia – Tuscan Estate, Boutique Villa
4 bedrooms, 4 king beds, 5 bathrooms
15–20 Aug
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Villa in Gaiole in Chianti
Villa Ridolfo, a property surrounded by vineyards
5 bedrooms, 5 beds, 5 bathrooms
28 Jul – 2 Aug
5.0 out of 5 average rating, 25 reviews
Superhost
Flat in Bossi
Restored barn in vineyards with a fireplace
2 bedrooms, 3 beds, 2 bathrooms
25–30 Jul
Guest favourite
Home in Radda in Chianti
Villa le Scope 5*
3 bedrooms, 4 beds, 3 bathrooms
28 Jul – 2 Aug
4.98 out of 5 average rating, 45 reviews
Top guest favourite
Room in Gaiole in Chianti
Medieval hilltop borgo amid Chianti vineyards
1 double bed, 1 bathroom
18–23 Mar
4.98 out of 5 average rating, 144 reviews
Top guest favourite
Villa in Gaiole in Chianti
Sestuccia
4 bedrooms, 4 king beds, 4 bathrooms
24–31 Oct
4.99 out of 5 average rating, 69 reviews
Flat in Gaiole in Chianti
Podere L'Aquila- Lavanda
3 bedrooms, 4 beds, 1 bathroom
6–11 Oct
Flat in Gaiole in Chianti
200-year-old home with valley views and pool
3 bedrooms, 4 beds, 2 bathrooms
27 Jul – 1 Aug
Guest favourite
Villa in Gaiole in Chianti
Casa Faraona, villa with private pool
3 bedrooms, 4 beds, 3 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 30 reviews
Flat in Gaiole in Chianti
A 13th-century mill with a pool
1 bedroom, 2 beds, 1 bathroom
8–13 Aug
Top guest favourite
Villa in Radda in Chianti
Organic winery estate in the Chianti hills
5 bedrooms, 5 king beds, 5 bathrooms
26–31 Oct
4.98 out of 5 average rating, 64 reviews
Top guest favourite
Cottage in Greve in Chianti
Greve Valley views and a private pool
3 bedrooms, 4 beds, 3 bathrooms
4–10 Oct
5.0 out of 5 average rating, 50 reviews
Superhost
Villa in Radda in Chianti
Vineyard views and a pool in Chianti
4 bedrooms, 4 double beds, 4 bathrooms
22–27 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Farm stay in Gaiole in Chianti
Le Miccine Villa in Tuscany for 6 w/ Pool
3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
4.92 out of 5 average rating, 12 reviews
Guest favourite
Villa in Gaiole in Chianti
Stone villa on a Chianti winery
2 bedrooms, 2 double beds, 2 bathrooms
31 Jul – 5 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Apartment in Cavriglia
Renovated stone barn with Arno Valley views
1 bedroom, 3 beds, 1 bathroom
16–21 Jul
4.89 out of 5 average rating, 180 reviews
Guest favourite
Home in Gaiole in Chianti
House in the heart of Chianti
2 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
4.95 out of 5 average rating, 21 reviews