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

Top guest favourite
Farm stay in Gaiole in Chianti
La Pieve - the house next to the church
2 bedrooms, 3 beds, 1 private bathroom
4–9 Nov
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4.96 out of 5 average rating, 111 reviews
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
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
7–12 Jul
Guest favourite
Villa in Gaiole in Chianti
Casa Faraona, villa with private pool
5.0 out of 5 average rating, 29 reviews, 3 bedrooms, 4 beds, 3 bathrooms
29 Aug – 3 Sept
Top guest favourite
Villa in Gaiole in Chianti
Villa Ridolfo, a property surrounded by vineyards
5.0 out of 5 average rating, 25 reviews, 5 bedrooms, 5 beds, 5 bathrooms
28 Jul – 2 Aug
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
5–10 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
Top guest favourite
Flat in Cavriglia
Apartment Comfort | Quiet Escape in Tuscany
5.0 out of 5 average rating, 13 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Aug
Home in Gaiole in Chianti
San Piero Terre, villa in the Chianti region.
4.67 out of 5 average rating, 18 reviews, 6 bedrooms, 11 beds, 4 bathrooms
12–17 Jul
Top guest favourite
Villa in Gaiole in Chianti
Montemarcoli
5.0 out of 5 average rating, 33 reviews, 2 bedrooms, 3 beds, 2 bathrooms
7–14 Nov
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
5–10 Jul
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
Superhost
Flat in Bossi
Villino Ersilia Music, the charm of Chianti
2 bedrooms, 3 beds, 2 bathrooms
8–13 Jul
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
8–13 Aug
Flat in Gaiole in Chianti
Mill in Chianti - Rosa
1 bedroom, 2 beds, 1 bathroom
5–10 Jul
Top guest favourite
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
4.97 out of 5 average rating, 72 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
16–21 Oct
Top guest favourite
Farm stay in Gaiole in Chianti
Le Rondini - where it all began
4.84 out of 5 average rating, 109 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Flat in Gaiole in Chianti
Podere L'Aquila- Lavanda
New place to stay, 3 bedrooms, 4 beds, 1 bathroom
6–11 Oct
Top guest favourite
Home in Montebenichi
[Little Escape] 4 Beds + Private Panoramic Pool
5.0 out of 5 average rating, 72 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
20–25 Aug