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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
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
Guest favourite
Flat in Cavriglia
Apartment Comfort | Quiet Escape in Tuscany
1 bedroom, 1 bed, 1 bathroom
26–31 Aug
5.0 out of 5 average rating, 15 reviews
Luxe
Villa in Gaiole in Chianti
Le Pratola
7 bedrooms, 11 beds, 7.5 bathrooms
4–9 Sept
5.0 out of 5 average rating, 6 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
Villa in Gaiole in Chianti
La Fornace di Tremoleto-Villa with Private Pool
3 bedrooms, 3 double beds, 2 bathrooms
26–31 Aug
5.0 out of 5 average rating, 12 reviews
Superhost
Holiday home in Montegonzi
Vino apartment 70 m2 view swimming pool
1 bedroom, 4 beds, 1 bathroom
28 Aug – 2 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Villa in Gaiole in Chianti
Sestuccina
2 bedrooms, 2 king beds, 2 bathrooms
31 Oct – 7 Nov
4.93 out of 5 average rating, 44 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
Top guest favourite
Home in Montebenichi
[Little Escape] 4 Beds + Private Panoramic Pool
2 bedrooms, 2 double beds, 1.5 bathrooms
4–9 Sept
5.0 out of 5 average rating, 73 reviews
Top guest favourite
Farm stay in Gaiole in Chianti
Le Rondini - where it all began
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
4.84 out of 5 average rating, 109 reviews
Top guest favourite
Villa in Gaiole in Chianti
Montemarcoli
2 bedrooms, 3 beds, 2 bathrooms
7–14 Nov
5.0 out of 5 average rating, 33 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
Villa in Montevarchi
Designer Villa with Private Garden & Jacuzzi
3 bedrooms, 3 king beds, 2 bathrooms
18–23 Jul
Guest favourite
Home in Gaiole in Chianti
1700s hilltop farmhouse with panoramic pool
7 bedrooms, 11 beds, 6 bathrooms
18–23 Oct
5.0 out of 5 average rating, 7 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
Home in Gaiole in Chianti
Medieval hamlet with castle views and pool
1 bedroom, 1 bed, 1 bathroom
12–17 Aug
Superhost
Flat in Cavriglia
Rustic-elegant apartment in the Chianti hills
2 bedrooms, 3 beds, 1 bathroom
16–21 Sept
Guest favourite
Cabin in Barbischio
Nice and cozy barn
3 bedrooms, 4 beds, 1 bathroom
1–6 Sept
4.89 out of 5 average rating, 66 reviews