Chianti Region Holiday Houses

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Our top choices for Chianti Region holiday homes

A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

1. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

Ruffoli

"Unable to sleep! Do not stay here during the summer. Even though it seemed to cool off at night, and even with a fan, it was so hot in the top bedroom that we sweat all night and did not sleep a wink. Also, there was a dog barking next door so that made it even harder to sleep. For some reason, there isn’t a pool listed in the description but when we complained about the heat, we were told we could use the pool. The property is beautiful but unbearable in terms of getting sleep, I do not...

Michael F.

includes taxes & fees

6 Nov - 7 Nov

A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

2. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

includes taxes & fees

16 Nov - 17 Nov

An outdoor patio with a table, chairs, and a view of a landscape.

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

Toscana

Kim

includes taxes & fees

6 Nov - 7 Nov

A view through a wooden door of a courtyard with stone walls and potted plants.

4. Chianti Craft House Badia a Passignano

Tavarnelle Val di Pesa

Oscar O.

includes taxes & fees

6 Nov - 7 Nov

A garden with a lawn, three white lounge chairs, and a pergola.

5. Apartment House with garden Tuscany Chianti , Florence 15km.

Toscana

Robert M.

includes taxes & fees

6 Nov - 7 Nov

An open doorway leading to an outdoor patio with a wooden table and chairs, a stone floor, and a wooden barrel with bottles.

6. Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC

Montespertoli

"We found sanctuary at this lovely farmhouse during the July heat wave--refreshing dip in the pool, relaxing dinner in the courtyard, restful sleep in the air-conditioned home. Got up to watch the sunrise over the vineyards, absolutely stunning scenery, and watched three hot air balloons also taking in the sights. Matteo was very welcoming, and we bridged the language barrier with a little help from Google translate. Wished we could have stayed longer!"

Susan A.

includes taxes & fees

16 Nov - 17 Nov

A modern kitchen with a tiled backsplash, a dining area with a table and chairs, and a staircase with a plant shelf.

7. A cozy little house

Loro Ciuffenna

includes taxes & fees

1 Dec - 2 Dec

A swimming pool with a wooden deck, a tree with red leaves, and a building with a beige facade.

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

Figline Valdarno

includes taxes & fees

19 Nov - 20 Nov

A brick building with a garden, a metal fence, and a clear sky.

9. Casa Marisa in Castellina in Chianti

Castellina in Chianti

includes taxes & fees

8 Nov - 9 Nov

A room with a view of a vineyard through an arched window, a bottle of wine, and a plate of fruit.

10. 7 min from Cantina Antinori in Chianti Classico | Pool | Casa Sala & Pepe

Tavarnelle Val di Pesa

includes taxes & fees

20 Nov - 21 Nov

An outdoor patio with a table, chairs, a grill, and a large umbrella.

11. Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi

Tavarnelle Val di Pesa

Ramona S.

includes taxes & fees

6 Nov - 7 Nov

A stone building with a gravel path, outdoor seating, and greenery.

12. The Arch Among the Hills of Castellina

Topina

includes taxes & fees

8 Nov - 9 Nov

A rustic interior with a stone fireplace, wooden beams, a sofa, and a staircase leading to a door.

13. Historic 'Felciolina' Country House with Private Terrace, 30 Minutes from Florence

Rignano sull'Arno

Anonymous traveller

includes taxes & fees

1 Dec - 2 Dec

A stone building with a tiled roof, a small window, and a door.

14. Mhateria Relais

Rignano Sull' Arno

Thomas K.

includes taxes & fees

9 Nov - 10 Nov

A living room with a TV, a sofa, and a dining area with chairs.

15. House with a separate entrance on the outskirts of Florence and Chianti

Impruneta

includes taxes & fees

9 Nov - 10 Nov

A patio with a table and chairs, an umbrella, and a view of a green fence and plants.

16. Holiday home 'Sandra House Certaldo' with private garden and Wi-Fi

Certaldo

Anonymous traveller

includes taxes & fees

10 Nov - 11 Nov

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and hills.

17. Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi

Montespertoli

includes taxes & fees

8 Nov - 9 Nov

A garden pathway leading to a stone building with a brick wall, a pergola, and a small brick structure in the background.

18. Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi

Bucine

"Upon arrival Guido had everything prepared for us. A bottle of his amazing wine that he makes along with 2 wine glasses we’re waiting on the farmhouse table. The home had 2 very comfortable bedrooms and a bathroom along with a living room and kitchen. Front porch overlooks the stunning Tuscany fields. The swimming pool was refreshing and everything was beyond perfect. This location was everything and more. The hosts were so helpful. I will come back her again..make sure to take time for the...

Marianne H.

includes taxes & fees

29 Nov - 30 Nov