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

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Chianti Region vacation homes

Exterior detail

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, (24 reviews)
"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...
Canada
James
The price is ￥14,652
￥28,805 total
includes taxes & fees
Sep 14 - Sep 15
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Interior

2. Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Tavarnelle Val di Pesa
10.0 out of 10, Exceptional, (12 reviews)
"Very historic venue, with amazing views"
United States
Oscar O.
The price is ￥22,681
￥32,842 total
includes taxes & fees
Sep 6 - Sep 7
Chianti Craft House Badia a Passignano
Outdoor dining

3. House with views of the Chianti

House with views of the Chianti
impruneta
10.0 out of 10, Exceptional, (4 reviews)
"My wife and I stayed here for our honeymoon and have already talked about returning here for an anniversary. This house was clean, charming and located in a beautiful area. The views from the property are stunning."
United States
Chase B.
The price is ￥12,886
￥42,287 total
includes taxes & fees
Oct 6 - Oct 7
House with views of the Chianti
Outdoor dining

4. Wonderful Tuscan farmhouse with large spaces and panoramic views

Wonderful Tuscan farmhouse with large spaces and panoramic views
impruneta
9.6 out of 10, Exceptional, (27 reviews)
"Lovely area. Charming house. "
United States
Christine F.
The price is ￥15,060
￥46,995 total
includes taxes & fees
Sep 8 - Sep 9
Wonderful Tuscan farmhouse with large spaces and panoramic views
Living area

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

casagreve - stylish house in Tuscan village - breathtaking view from its terrace
Greve in Chianti
10.0 out of 10, Exceptional, (10 reviews)
"This was my favorite stay during our travels throughout Italy. Restaurants on the square or dining out on the lovely balcony. We had a wonderful stay here. Perfect location for dayctrips to Sienna and Florence, bike riding through Tuscany, . Great hosts as well!"
United States
Linda L.
The price is ￥58,063
￥65,502 total
includes taxes & fees
Sep 6 - Sep 7
casagreve - stylish house in Tuscan village - breathtaking view from its terrace
Interior

6. Fornace di Bonazza - wonderful house among the Chianti hills

Fornace di Bonazza - wonderful house among the Chianti hills
Tavarnelle Val di Pesa
10.0 out of 10, Exceptional, (2 reviews)
"Great property and home!"
United States
Anonymous traveler
Fornace di Bonazza - wonderful house among the Chianti hills
Outdoor dining

7. 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 ￥10,617
￥19,691 total
includes taxes & fees
Sep 8 - Sep 9
Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi
Property grounds

8. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is ￥39,193
￥48,991 total
includes taxes & fees
Sep 6 - Sep 7
Casa Marisa in Castellina in Chianti
Outdoor dining

9. 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 ￥21,911
￥22,455 total
includes taxes & fees
Sep 6 - Sep 7
Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi
Outdoor dining

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

Blue villa surrounded by greenery between Arezzo Florence and Siena
TERRANUOVA BRACCIOLINI
Blue villa surrounded by greenery between Arezzo Florence and Siena
Outdoor dining

11. 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 ￥29,945
￥30,308 total
includes taxes & fees
Sep 28 - Sep 29
Historic 'Felciolina' Country House with Private Terrace, 30 Minutes from Florence
Outdoor dining

12. 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 ￥44,582
￥54,380 total
includes taxes & fees
Oct 1 - Oct 2
Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi
Pool

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

Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
The price is ￥26,129
￥26,492 total
includes taxes & fees
Sep 8 - Sep 9
Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
Pool

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

Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (1 review)
"Pros: The view and unique traditional apartment. Cons: -"
United States
Anonymous traveler
The price is ￥55,535
￥67,150 total
includes taxes & fees
Sep 6 - Sep 7
Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi
Interior

15. 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 ￥50,806
￥95,080 total
includes taxes & fees
Sep 8 - Sep 9
Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC
Pool

16. Farmhouse in Chianti

Farmhouse in Chianti
gaiole in chianti
9.8 out of 10, Exceptional, (6 reviews)
"This location provided our blended family an authentic experience in a small village on top of a mountain in Chianti. The house is surrounded by olive groves and wine grapes. The pool was great and the village, literally less than a city block up the road. Folks are incredibly friendly and helpful. Two of the rooms had their own bathrooms and the other two share a bathroom. There is a common kitchen for cooking and eating. We cooked most nights and ate on the outside terrace. Allesandra is a...
United States
Lara W.
The price is ￥73,487
￥90,090 total
includes taxes & fees
Sep 13 - Sep 14
Farmhouse in Chianti
Interior

17. Little cozy house

Little cozy house
Loro Ciuffenna
The price is ￥12,701
￥15,967 total
includes taxes & fees
Sep 11 - Sep 12
Little cozy house
Interior

18. THE CASINA OF SANT 'AGOSTINO

THE CASINA OF SANT 'AGOSTINO
Colle di Val d'Elsa
The price is ￥21,774
￥27,619 total
includes taxes & fees
Sep 8 - Sep 9
THE CASINA OF SANT 'AGOSTINO
Outdoor dining

19. Raffaello Apartment with garden

Raffaello Apartment with garden
San Gersolé-torre Rosse
The price is ￥26,970
￥59,424 total
includes taxes & fees
Oct 2 - Oct 3
Raffaello Apartment with garden
Dining

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

Holiday Home 'Poggio Loccano' with Private Garden and Balcony
Montevarchi
The price is ￥34,294
￥52,439 total
includes taxes & fees
Sep 6 - Sep 7
Holiday Home 'Poggio Loccano' with Private Garden and Balcony
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.
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Top Chianti Region Hotel Reviews

Fattoria di Vegi

Fattoria di Vegi

10/10 Excellent
"Amazing! I wish I could have stayed forever!"
Christopher 1-night trip
Posted 19 hours ago
Fattoria di Vegi

Find out more about Chianti Region

Chianti Region Vacation Homes information

Number of reviews
80
Accommodation
417 Vacation Homes
Lowest Price
￥15,967
Highest Price
￥95,080

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