A stone castle with battlements overlooking a lush valley with vineyards.

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Gaiole in Chianti holiday homes

Interior

'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi

'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Gaiole in Chianti
The price is £550
includes taxes & fees
15 Jul - 16 Jul
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Outdoor pool

Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.2 out of 10, Wonderful, (10 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is £105
includes taxes & fees
1 Aug - 2 Aug
Casa Vacanze Le Case
Interior

Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Barberino Tavarnelle
10.0 out of 10, Exceptional, (12 reviews)
"Very historic venue, with amazing views"
United States
Oscar O.
The price is £165
includes taxes & fees
14 Jul - 15 Jul
Chianti Craft House Badia a Passignano
Exterior

Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning

Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning
Buonconvento
The price is £103
includes taxes & fees
2 Jul - 3 Jul
Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning
Outdoor dining

Dolce Casa 2 by Tiny Away

Dolce Casa 2 by Tiny Away
Arezzo
The price is £92
includes taxes & fees
9 Jul - 10 Jul
Dolce Casa 2 by Tiny Away
1 bedroom, WiFi, bed sheets

Dolce Casa 1 by Tiny Away

Dolce Casa 1 by Tiny Away
Arrezo
The price is £97
includes taxes & fees
5 Jul - 6 Jul
Dolce Casa 1 by Tiny Away
Spa

Love Nest Siena: Romantic Suite with SPA & Jacuzzi

Love Nest Siena: Romantic Suite with SPA & Jacuzzi
Toscana
The price is £150
includes taxes & fees
8 Jul - 9 Jul
Love Nest Siena: Romantic Suite with SPA & Jacuzzi
Exterior

Tolletta 10 e Lode - One Bedroom House, Sleeps 4

Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Arezzo Centro Storico
10.0 out of 10, Exceptional, (1 review)
" La casa pulitissima è molto bella, l’host molto disponibile e gentile, risponde sempre e anche subito. La posizione ottimale per fare il giro dei mercatini e di tutta la città. Consigliatissima "
Italy
Maria Gemma
The price is £137
includes taxes & fees
8 Jul - 9 Jul
Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Outdoor dining

Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi

Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi
Certaldo
10.0 out of 10, Exceptional, (1 review)
"Pros: Die familiäre Aufnahme und Unterstützung war sehr angenehm."
Germany
Anonymous traveller
The price is £163
includes taxes & fees
2 Jul - 3 Jul
Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi
Outdoor dining

House with views of the Chianti

House with views of the Chianti
impruneta
10.0 out of 10, Exceptional, (4 reviews)
"My wife and I stayed here for our honeymoon and have already talked about returning here for an anniversary. This house was clean, charming and located in a beautiful area. The views from the property are stunning."
United States
Chase B.
The price is £216
includes taxes & fees
5 Jul - 6 Jul
House with views of the Chianti
Exterior detail

Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning

Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
Foiano della Chiana
The price is £70
includes taxes & fees
10 Jul - 11 Jul
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
Outdoor dining

Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is £233
includes taxes & fees
5 Jul - 6 Jul
Casa Marisa in Castellina in Chianti
1 bedroom, in-room safe, desk, iron/ironing board

The Wishing Well - The Wishing Well

The Wishing Well - The Wishing Well
Firenze
9.2 out of 10, Wonderful, (5 reviews)
"House was very clean and close enough to the city without the noise or traffic. Host is lovely and responds promptly. Definitely would book again."
Canada
Grace M.
The price is £186
includes taxes & fees
7 Jul - 8 Jul
The Wishing Well - The Wishing Well
Property grounds

country house with garden ,pool,children's play area ,Tuscany,15 from Florence

country house with garden ,pool,children's play area ,Tuscany,15 from Florence
Toscana
9.8 out of 10, Exceptional, (82 reviews)
"The hostess Sonia was fabulous."
United States
Kim
The price is £211
includes taxes & fees
2 Jul - 3 Jul
country house with garden ,pool,children's play area ,Tuscany,15 from Florence
Outdoor dining

Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi

Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi
Figline Valdarno
The price is £93
includes taxes & fees
2 Jul - 3 Jul
Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi
Terrace/patio

Charming Siena Countryside Stay

Charming Siena Countryside Stay
Monterongriffoli
The price is £314
includes taxes & fees
4 Jul - 5 Jul
Charming Siena Countryside Stay
Outdoor dining

Casa Crevole di Martina in the Heart of Tuscany

Casa Crevole di Martina in the Heart of Tuscany
Murlo
10.0 out of 10, Exceptional, (1 review)
"Nach einer herzlichen Begrüßung durch die Gastgeberin haben wir ein paar entspannte Tage verbracht. Im Kühlschrank befanden sich für uns schon einmal keiner Erfrischungen. Obwohl wir nur 4 Nächte blieben, gab es einen Handtuchtausch nach 2 Tagen. Total überrascht hat uns aber der selbstgebackene Kuchen der für uns bereit stand. Wir würden hier jeder Zeit wieder Urlaub machen und können die Unterkunft mehr wir nur empehlen."
Germany
Sybille F.
The price is £229
includes taxes & fees
2 Jul - 3 Jul
Casa Crevole di Martina in the Heart of Tuscany
Interior

Holiday Home 'La Casina All'angolo'

Holiday Home 'La Casina All'angolo'
Civitella in Val di Chiana
The price is £113
includes taxes & fees
7 Jul - 8 Jul
Holiday Home 'La Casina All'angolo'
Terrace/patio

Charming bungalow with whirlpool in Tuscany: peace, nature and comfort

Charming bungalow with whirlpool in Tuscany: peace, nature and comfort
Antria
The price is £140
includes taxes & fees
2 Jul - 3 Jul
Charming bungalow with whirlpool in Tuscany: peace, nature and comfort
Dining

Holiday Home 'Poggio Loccano' with Private Garden and Balcony

Holiday Home 'Poggio Loccano' with Private Garden and Balcony
Montevarchi
The price is £241
includes taxes & fees
15 Jul - 16 Jul
Holiday Home 'Poggio Loccano' with Private Garden and Balcony
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Gaiole in Chianti Hotel Reviews

Hotel Chiusarelli

Hotel Chiusarelli

10/10 Excellent
"Great stay. Beautiful property and the staff are so helpful and friendly. Hotel is on the edge of the historic center and ideally located. We will return!"
Richard 1-night trip
Posted 17 hours ago
Hotel Chiusarelli

Find out more about Gaiole in Chianti

Gaiole in Chianti Holiday Homes information

Number of reviews
116
Accommodation
1493 Holiday Homes
Lowest Price
£70
Highest Price
£550