Chianti Region Holiday Homes from €93: Search Top House Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

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

"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...

James

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

8 Nov - 9 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 various plants and flowers, a pathway, and a swing set.

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

15 Nov - 16 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

17 Nov - 18 Nov

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

9. Casa Marisa in Castellina in Chianti

Castellina in Chianti

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

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.

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

12. The Arch Among the Hills of Castellina

Topina

A wooden table with two wine glasses and a bottle of wine, set outdoors with a view of greenery and hills.

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

18 Nov - 19 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

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

8 Nov - 9 Nov

An aerial view of a traditional villa with multiple buildings, surrounded by lush greenery and trees.

17. Cosy apartment for 6 people with WIFI, pool, A/C, TV, balcony and pets allowed, close to Florence

Impruneta

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

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

Montespertoli

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

19. 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

A stone building with a covered outdoor seating area and a brick pathway.

20. Apartment 'La Ripa - Master' with Shared Pool and Wi-Fi

San Gimignano

Anne-Marie M.

View all properties

Find holiday rentals that suit your style

Villas

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Chianti Region Hotel Reviews

Salvadonica - Borgo del Chianti

10/10 Excellent

"Muy buena atención y ubicación inmejorable."

Borgo Vescine

10/10 Excellent

"There are no words to describe our experience at this incredibly beautiful and wonderful charming several century old village resort in Chianti. It was everything you imagined Italy to be in wine country. Probably one of my favorite places I have ever stayed at, and I’ve stayed at hundreds of of places around the world. The staff was wonderful, the accommodations were just super cool. It was once a village dating back over 100+ years. It was truly remarkable that the owner discovered it and restored it, creating a truly wonderful experience and beautiful Tuscany. We definitely will stay here every time we go to Tuscany in the future. This is a must-stay place!"

hu Firenze Certosa camping in town

8/10 Good

"Great location, superior tent was really nice with the en-suite and balcony. Easy check in. Staff friendly and helpful. Downsides were no designated parking space for us despite not all tents being occupied. Also bread given out at dinner were not free despite us not asking for them and at €6 a bag it was not great value. The bread was pretty hard and tasteless! Regardless I would recommend a stay here in the heart of Tuscany and within half an hour bus ride into Florence ♥️🇮🇹"

Hotel Villa Cesi

10/10 Excellent

"Rooms are very clean and staff are very friendly and super helpful and above all they are caring and very accommodating especially with our elderly less abled parents for which we are very grateful. Property is in a beautiful setting. Restaurant staff also very helpful. Thank you very much to all who hosted us at Villa Cesi."

Find out more about Chianti Region

Chianti Region Holiday Homes information

Number of reviews	216
Accommodation	395 Holiday Homes
Lowest Price	€93
Highest Price	€403

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chianti Region holiday homes