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

Search Vacation Homes in Chianti Region

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chianti Region vacation homes

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

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
9.2 out of 10, Wonderful, (28 reviews)
"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...
United States
Michael F.
The price is AED 333
AED 626 total
includes taxes & fees
12 Nov - 13 Nov
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

2. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
The price is AED 415
AED 473 total
includes taxes & fees
28 Nov - 29 Nov
Agriturismo La Ferrozzola

3. 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, (83 reviews)
"The hostess Sonia was fabulous."
United States
Kim
The price is AED 445
AED 598 total
includes taxes & fees
7 Nov - 8 Nov
country house with garden ,pool,children's play area ,Tuscany,15 from Florence

4. Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Tavarnelle Val di Pesa
10.0 out of 10, Exceptional, (13 reviews)
"Very historic venue, with amazing views"
United States
Oscar O.
The price is AED 516
AED 713 total
includes taxes & fees
11 Nov - 12 Nov
Chianti Craft House Badia a Passignano

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

Apartment House with garden Tuscany Chianti , Florence 15km.
Toscana
9.8 out of 10, Exceptional, (75 reviews)
"Great property, well equipped, nice views, well maintained, very friendly and helpful host. We did really enjoy our stay :-)"
Germany
Robert M.
The price is AED 495
AED 648 total
includes taxes & fees
7 Nov - 8 Nov
Apartment House with garden Tuscany Chianti , Florence 15km.

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

Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC
Montespertoli
10.0 out of 10, Exceptional, (1 review)
"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!"
United States
Susan A.
The price is AED 495
AED 1,329 total
includes taxes & fees
15 Nov - 16 Nov
Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC

7. A cozy little house

A cozy little house
Loro Ciuffenna
The price is AED 326
AED 371 total
includes taxes & fees
1 Dec - 2 Dec
A cozy little house

8. 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 AED 230
AED 453 total
includes taxes & fees
17 Nov - 18 Nov
Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi

9. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is AED 891
AED 1,114 total
includes taxes & fees
8 Nov - 9 Nov
Casa Marisa in Castellina in Chianti

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

7 min from Cantina Antinori in Chianti Classico | Pool | Casa Sala & Pepe
Tavarnelle Val di Pesa
The price is AED 751
AED 1,028 total
includes taxes & fees
22 Nov - 23 Nov
7 min from Cantina Antinori in Chianti Classico | Pool | Casa Sala & Pepe

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

Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi
Tavarnelle Val di Pesa
10.0 out of 10, Exceptional, (1 review)
"Das Objekt liegt zwischen Florenz und Siena umgeben von Olivenbäumen. Die Lage ist perfekt für Ausflüge."
Germany
Ramona S.
The price is AED 984
AED 1,207 total
includes taxes & fees
6 Dec - 7 Dec
Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi

12. The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
The price is AED 891
AED 1,052 total
includes taxes & fees
8 Nov - 9 Nov
The Arch Among the Hills of Castellina

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

Historic 'Felciolina' Country House with Private Terrace, 30 Minutes from Florence
Rignano sull'Arno
8.0 out of 10, Very good, (1 review)
"Pros: Alles was goed voorbereid en ruim aanwezig. Keuken/kook benodigdheden, shampoos, fles wijn, fruitmandje met bananen en appels. Pro-actief en vriendelijk optreden van de host; zo werd verwarming aangezet bij minder goed weer. Cons: Niet van toepassing. We hebben een hele fijne week gehad."
Netherlands
Anonymous traveler
The price is AED 734
AED 751 total
includes taxes & fees
1 Dec - 2 Dec
Historic 'Felciolina' Country House with Private Terrace, 30 Minutes from Florence

14. Mhateria Relais

Mhateria Relais
Rignano Sull' Arno
10.0 out of 10, Exceptional, (1 review)
"Eine tolle Immobilie, die tatsächlich so gut wie sie beschrieben ist, auch ist."
Germany
Thomas K.
The price is AED 928
AED 1,095 total
includes taxes & fees
8 Nov - 9 Nov
Mhateria Relais

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

House with a separate entrance on the outskirts of Florence and Chianti
Impruneta
The price is AED 371
AED 640 total
includes taxes & fees
9 Nov - 10 Nov
House with a separate entrance on the outskirts of Florence and Chianti

16. 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 traveler
The price is AED 824
AED 837 total
includes taxes & fees
12 Nov - 13 Nov
Holiday home 'Sandra House Certaldo' with private garden and Wi-Fi

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

Cosy apartment for 6 guests with pool, WIFI, A/C, TV, balcony and pets allowed, close to Florence
Impruneta
The price is AED 535
AED 716 total
includes taxes & fees
1 Dec - 2 Dec
Cosy apartment for 6 guests with pool, WIFI, A/C, TV, balcony and pets allowed, close to Florence

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

Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
The price is AED 1,144
AED 1,152 total
includes taxes & fees
7 Nov - 8 Nov
Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi

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

Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi
Bucine
10.0 out of 10, Exceptional, (2 reviews)
"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...
United States
Marianne H.
The price is AED 1,485
AED 1,662 total
includes taxes & fees
29 Nov - 30 Nov
Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi

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

Apartment 'La Ripa - Master' with Shared Pool and Wi-Fi
San Gimignano
10.0 out of 10, Exceptional, (1 review)
"We stayed for a week at La Ripa. It is a very beautiful and quiet place. It is a few minutes from San Gimignano and it is a central place to visit nice villages in Toscany. Rodrigo was there to welcome us and securing for us an optimal stay. He was amicable and available. This is a place we are highly recommending."
Canada
Anne-Marie M.
Apartment 'La Ripa - Master' with Shared Pool and Wi-Fi
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chianti Region Hotel Reviews

Explore a world of travel with Expedia