Chianti Region Vacation Homes from ￥15,871

A vineyard with rows of grapevines, a house surrounded by trees, and a road with vehicles.

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Our top choices for Chianti Region vacation 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

￥28,993 total

includes taxes & fees

Sep 29 - Sep 30

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

2. Chianti Craft House Badia a Passignano

Tavarnelle Val di Pesa

Oscar O.

￥32,645 total

includes taxes & fees

Sep 24 - Sep 25

A stone building with a courtyard, a table with chairs, and a wheelbarrow.

3. House with views of the Chianti

impruneta

Chase B.

￥43,106 total

includes taxes & fees

Sep 23 - Sep 24

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

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

Figline Valdarno

￥22,887 total

includes taxes & fees

Sep 27 - Sep 28

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

5. Little cozy house

Loro Ciuffenna

￥15,871 total

includes taxes & fees

Sep 24 - Sep 25

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

6. Casa Marisa in Castellina in Chianti

Castellina in Chianti

￥48,697 total

includes taxes & fees

Sep 29 - Sep 30

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

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

Certaldo

Anonymous traveler

￥19,942 total

includes taxes & fees

Sep 28 - Sep 29

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

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

Montespertoli

￥26,333 total

includes taxes & fees

Sep 23 - Sep 24

A room with a large sliding glass door leading to a pool area with a view of rolling hills and a distant village.

9. Your nest in the Tuscany countryside

Certaldo - Firenze

￥41,303 total

includes taxes & fees

Oct 11 - Oct 12

A dining area with a brick archway, wooden dining table, chairs, and a chandelier.

10. Holiday Home 'Poggio Loccano' with Private Garden and Balcony

Montevarchi

￥52,124 total

includes taxes & fees

Sep 23 - Sep 24

An outdoor wooden pavilion with a brick wall, a picnic table, and potted plants.

11. Apartment "Bilocale Vermiglio" with Shared Pool & Wi-Fi

Castiglion Fibocchi

"Pros: Il giardino è bellissimo e curato, bella la piscina, abbiamo apprezzato anche il fatto che ci siano tavoli e panche per sedersi, gustarsi il tramonto, il pranzo o la cena nella propria privacy. L'esterno in generale è un luogo davvero rilassante. Ci sono molti spazi per i bambini. I proprietari sono stati gentili, estremamente disponibili ed è stato davvero piacevole scambiare delle chiacchiere. Cons: Il letto è un po' scomodo e il bagno è molto piccolo, privo di bidet con la porta molto...

Anonymous traveler

￥20,345 total

includes taxes & fees

Sep 26 - Sep 27

A living room with a dining table, two sofas, a coffee table, and a ceiling fan.

12. casagreve - stylish house in Tuscan village - breathtaking view from its terrace

Greve in Chianti

Linda L.

An outdoor patio with a wooden pergola, a sofa, a table, and chairs.

13. Blue villa surrounded by greenery between Arezzo Florence and Siena

TERRANUOVA BRACCIOLINI

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

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

Rignano sull'Arno

Anonymous traveler

￥25,251 total

includes taxes & fees

Oct 2 - Oct 3

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

15. 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.

￥74,488 total

includes taxes & fees

Oct 19 - Oct 20

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

16. House with separate entrance at the gates of Florence and Chianti

Impruneta

￥35,170 total

includes taxes & fees

Oct 4 - Oct 5

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

17. The Arch Among the Hills of Castellina

Topina

￥53,928 total

includes taxes & fees

Oct 1 - Oct 2

A covered patio with a wooden table and chairs, stone walls, and a view of a garden.

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

Bucine

Anonymous traveler

￥71,423 total

includes taxes & fees

Sep 25 - Sep 26

A rectangular swimming pool with a wooden deck and metal railing, surrounded by a grassy area with trees and a clear sky.

19. Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi

Castelnuovo Berardenga

Anonymous traveler

￥68,825 total

includes taxes & fees

Sep 23 - Sep 24

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

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

Tavarnelle Val di Pesa

Ramona S.

￥54,053 total

includes taxes & fees

Oct 17 - Oct 18

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Top Chianti Region Hotel Reviews

Hu Norcenni Girasole Village

10/10 Excellent

"Perfect can’t fault it. Maybe a bigger train/bus at peak times would help. Lovely restaurant, bars, ice cream. Clean swimming pools. Good, kind, friendly staff. Safe place. Clean accommodation. Peaceful environment. Must take mosquito treatment as they’re bad out here. Lovely bonus is the pump at the pools to pump donuts up. Can’t fault it. Will 100000% return."

Castello Vicchiomaggio

10/10 Excellent

"very nice historic hotel with great views of the country side and great atmphere. Room size and ammenities were wonderful. The breakfeast was great. Restaurant was nice with historic dishes. Only down side was the gluten and nut free options were limited...mainly for gluten sufferers, since the only gluten free pasta is Penne, which is not great for all dishes and frustratingsince Italy produces a very large variety of great gluten free pasta shapes. Also, my travel partner and I did the same pasta, one gluten free (penne) and one not gluten free. The non-gluten-free pasta came beautifully presented, while the gluten-free pasta came like it was thrown together last minute… like as if you were sitting at your own kitchen table. Impression given with the dinner is that people with allergies, are more a bit of a bother, and the typical mission in Italy, to give visitors an excellent culinary experience, is more less abandoned for people with allergies. that said, accommodating allergies is very difficult these days and at least the menu was clear about which foods contain which allergens."

Fattoria di Vegi

10/10 Excellent

"What an amazing hotel. The attention to detail on the refurb of the property is phenomenal. Once the tennis court, spa etc are completed this will easily be high hundreds per night. We visited all the other properties in the surrounding area and nothing came close to this hotel. The food and drinks were also brilliant - best meal we had in Tuscany was in the hotel. My only suggestions would be to rotate the staff more - they seemed slightly over worked. Easily one of the best hotels I have stayed in."

Find out more about Chianti Region

Chianti Region Vacation Homes information

Number of reviews	52
Accommodation	417 Vacation Homes
Lowest Price	￥15,871
Highest Price	￥74,488

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chianti Region vacation homes

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

2. Chianti Craft House Badia a Passignano

3. House with views of the Chianti

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

5. Little cozy house

6. Casa Marisa in Castellina in Chianti

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

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

9. Your nest in the Tuscany countryside

10. Holiday Home 'Poggio Loccano' with Private Garden and Balcony

11. Apartment "Bilocale Vermiglio" with Shared Pool & Wi-Fi

12. casagreve - stylish house in Tuscan village - breathtaking view from its terrace

13. Blue villa surrounded by greenery between Arezzo Florence and Siena

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

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

16. House with separate entrance at the gates of Florence and Chianti

17. The Arch Among the Hills of Castellina

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

19. Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi

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

Find vacation rentals that suit your style

Top Chianti Region Hotel Reviews

Hu Norcenni Girasole Village

Salvadonica - Borgo del Chianti

Relais Vignale & Spa

Park Hotel Chianti

Castello Vicchiomaggio

Palagina la Dimora

Fattoria di Vegi

Castello di Spaltenna- Small Luxury Hotels of the World

hu Firenze Certosa camping in town

Find out more about Chianti Region

Chianti Region Vacation Homes information

Explore a world of travel with Expedia

Search Vacation Homes in Chianti Region

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chianti Region vacation homes

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

2. Chianti Craft House Badia a Passignano

3. House with views of the Chianti

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

5. Little cozy house

6. Casa Marisa in Castellina in Chianti

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

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

9. Your nest in the Tuscany countryside

10. Holiday Home 'Poggio Loccano' with Private Garden and Balcony

11. Apartment "Bilocale Vermiglio" with Shared Pool & Wi-Fi

12. casagreve - stylish house in Tuscan village - breathtaking view from its terrace

13. Blue villa surrounded by greenery between Arezzo Florence and Siena

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

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

16. House with separate entrance at the gates of Florence and Chianti

17. The Arch Among the Hills of Castellina

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

19. Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi

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

Find vacation rentals that suit your style

Top Chianti Region Hotel Reviews

Hu Norcenni Girasole Village

Find out more about Chianti Region

Chianti Region Vacation Homes information

Explore a world of travel with Expedia