Chianti Region Vacation Homes from ￥19,332

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

￥28,416 total

includes taxes & fees

Oct 2 - Oct 3

A garden with various plants and flowers, a pathway, and a swing set.

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

Toscana

Robert M.

￥27,208 total

includes taxes & fees

Sep 30 - Oct 1

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

3. Chianti Craft House Badia a Passignano

Tavarnelle Val di Pesa

Oscar O.

￥32,041 total

includes taxes & fees

Oct 5 - Oct 6

A stone building with a courtyard, outdoor seating, and potted plants.

4. Wonderful Tuscan farmhouse with large spaces and panoramic views

impruneta

Christine F.

￥43,855 total

includes taxes & fees

Oct 21 - Oct 22

A poolside setting with two glasses of red drink, a tray with snacks, and a white umbrella.

5. House in the Florentine hills with swimming pool, free parking and wifi

Reggello provincia Firenze

Peter L.

￥19,690 total

includes taxes & fees

Sep 30 - Oct 1

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

6. House with views of the Chianti

impruneta

Chase B.

￥40,275 total

includes taxes & fees

Oct 14 - Oct 15

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

7. Casa Marisa in Castellina in Chianti

Castellina in Chianti

￥48,372 total

includes taxes & fees

Sep 30 - Oct 1

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

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

Greve in Chianti

Linda L.

￥61,217 total

includes taxes & fees

Oct 1 - Oct 2

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

9. 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.

￥71,777 total

includes taxes & fees

Oct 25 - Oct 26

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

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

Figline Valdarno

￥19,332 total

includes taxes & fees

Oct 7 - Oct 8

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

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

Montevarchi

￥58,980 total

includes taxes & fees

Sep 30 - Oct 1

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

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

Rignano sull'Arno

Anonymous traveler

￥22,589 total

includes taxes & fees

Oct 2 - Oct 3

A swimming pool with a colorful inflatable ring and a water fountain.

13. Farmhouse in Chianti

gaiole in chianti

"We absolutely loved the pool and the view. The pool with a deep end and color changing light was our highlight. The hosts were very friendly, helpful and always available if needed, since they live upstairs in the same house. Still, they never complained about us being loud. Everything was perfectly clean, the pool was cleaned regularly during our stay. The road to the property might be rough, but the view is beautiful. Also, we were gifted some delicious wine."

Johanna K.

￥84,755 total

includes taxes & fees

Oct 1 - Oct 2

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

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

Montespertoli

￥26,134 total

includes taxes & fees

Sep 30 - Oct 1

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

15. Your nest in the Tuscany countryside

Certaldo - Firenze

￥40,454 total

includes taxes & fees

Oct 11 - Oct 12

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

16. The Arch Among the Hills of Castellina

Topina

￥48,866 total

includes taxes & fees

Oct 1 - Oct 2

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

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

TERRANUOVA BRACCIOLINI

￥32,757 total

includes taxes & fees

Oct 1 - Oct 2

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

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

Tavarnelle Val di Pesa

Ramona S.

￥51,446 total

includes taxes & fees

Oct 6 - Oct 7

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

￥71,599 total

includes taxes & fees

Oct 13 - Oct 14

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

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

Bucine

Anonymous traveler

￥70,955 total

includes taxes & fees

Sep 30 - Oct 1

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Top Chianti Region Hotel Reviews

Fattoria di Vegi

10/10 Excellent

"We had a lovely night stay at this villa in September. It is a 900 year-old hunting lodge that has been converted to spacious rooms many with balconies. The views are incredible, the rooms have been renovated with character fixtures, but includes excellent air-conditioning. The view from the pool was out of a storybook. Staff was attentive and very nice to deal with. The grounds have endless opportunities for photos at every turn. Try to explore the grounds a little - including the painters studio with is exquisite. It has only been open four months so there are a few bugs but overall, the stay was excellent. The one area they need to improve however is the food. The selections are pretty limited and the quality was not to the standard of the property. My recommendation is have the breakfast on site and lunch by the pool, but try the surrounding towns for dinner. Castellini in Chianti is a small town 15 minutes away with great choices. One Belvedere and their sister property Locanda are both within 2 kms and have high end dining. Overall I highly recommend this villa for a unique Tuscan experience."

Hu Norcenni Girasole Village

10/10 Excellent

"My family and I had such a great time. Such a kid friendly place and at check in they even had a little playground while you waiting and gave the kids bubbles. So great to be in nature and all of the amenities were lovely. The waterparks that were padded on the ground were genius and we did a family wine tasting which was such a lovely memory. Our stay was so nice with the deck and the grocery store is so affordable for dinners in. Love love love! My toddler played all day and there were so many times we got to relax because they had everything that we wanted or needed right on property."

Find out more about Chianti Region

Chianti Region Vacation Homes information

Number of reviews	172
Accommodation	447 Vacation Homes
Lowest Price	￥19,332
Highest Price	￥84,755

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

3. Chianti Craft House Badia a Passignano

4. Wonderful Tuscan farmhouse with large spaces and panoramic views