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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
Stone villa with town views and hot tub
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
Home in Lecchi
13th-century stone house with panoramic terrace
2 bedrooms, 4 beds, 2 bathrooms
24–29 Jul
4.96 out of 5 average rating, 240 reviews
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
Villa in Gaiole in Chianti
Wine estate villa in Chianti Classico
5 bedrooms, 5 beds, 5 bathrooms
28 Jul – 2 Aug
5.0 out of 5 average rating, 25 reviews
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
200-year-old home with valley views and pool
3 bedrooms, 4 beds, 2 bathrooms
27 Jul – 1 Aug
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 Gaiole in Chianti
Sestuccia
4 bedrooms, 4 king beds, 4 bathrooms
24–31 Oct
4.99 out of 5 average rating, 69 reviews
Guest favourite
Villa in Gaiole in Chianti
Secluded Chianti villa with 180-degree views
3 bedrooms, 4 beds, 3 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 30 reviews
Guest favourite
Flat in Cavriglia
Ancient borgo with a panoramic pool
1 bedroom, 1 bed, 1 bathroom
26–31 Aug
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Villa in Radda in Chianti
Tuscan character, contemporary style and comfort
5 bedrooms, 5 king beds, 5 bathrooms
26–31 Oct
4.98 out of 5 average rating, 64 reviews
Top guest favourite
Flat in San Gusmè
Beautiful medieval village!!!
2 bedrooms, 2 double beds, 2 bathrooms
26–31 Oct
4.99 out of 5 average rating, 460 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
Flat in San Gusmè
Elegant apartment in the heart of Chianti
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.99 out of 5 average rating, 160 reviews
Top guest favourite
Farm stay in Radda in Chianti
1500s farmhouse with a private lake
2 bedrooms, 3 beds, 1 bathroom
5–11 Aug
4.97 out of 5 average rating, 101 reviews
Top guest favourite
Room in Gaiole in Chianti
Medieval hilltop borgo amid Chianti vineyards
1 double bed, 1 bathroom
1–6 Aug
4.97 out of 5 average rating, 129 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