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 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

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 ￥14,976
￥29,813 total
includes taxes & fees
Aug 31 - Sep 1
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Property grounds

2. 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 ￥25,238
￥40,095 total
includes taxes & fees
Sep 2 - Sep 3
country house with garden ,pool,children's play area ,Tuscany,15 from Florence
Interior

3. Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Barberino Tavarnelle
10.0 out of 10, Exceptional, (12 reviews)
"Very historic venue, with amazing views"
United States
Oscar O.
The price is ￥20,864
￥31,250 total
includes taxes & fees
Aug 30 - Aug 31
Chianti Craft House Badia a Passignano
Property grounds

4. Villa with large garden in the Chianti hills

Villa with large garden in the Chianti hills
Siena
9.6 out of 10, Exceptional, (81 reviews)
"It was a little tricky finding the villa but worth it. Better instructions would be helpful. The home was lovely. The gardens wonderful. A great respite fromThe city."
United States
Julie H.
Villa with large garden in the Chianti hills
Outdoor dining

5. 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 ￥12,982
￥43,027 total
includes taxes & fees
Aug 30 - Aug 31
House with views of the Chianti
Outdoor dining

6. 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 ￥15,393
￥48,034 total
includes taxes & fees
Sep 4 - Sep 5
Wonderful Tuscan farmhouse with large spaces and panoramic views
Interior

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

Fornace di Bonazza - wonderful house among the Chianti hills
Barberino Tavarnelle
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
Living area

8. 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 ￥59,348
￥67,508 total
includes taxes & fees
Aug 30 - Aug 31
casagreve - stylish house in Tuscan village - breathtaking view from its terrace
Outdoor dining

9. 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 ￥11,128
￥20,401 total
includes taxes & fees
Sep 28 - Sep 29
Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi
TV

10. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is ￥40,060
￥50,075 total
includes taxes & fees
Sep 7 - Sep 8
Casa Marisa in Castellina in Chianti
Interior

11. 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 ￥51,929
￥96,996 total
includes taxes & fees
Sep 24 - Sep 25
Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC
Outdoor dining

12. 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 ￥22,391
￥22,947 total
includes taxes & fees
Sep 2 - Sep 3
Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi
Outdoor dining

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 ￥30,601
￥30,972 total
includes taxes & fees
Sep 28 - Sep 29
Historic 'Felciolina' Country House with Private Terrace, 30 Minutes from Florence
Outdoor pool

14. 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 ￥75,112
￥93,380 total
includes taxes & fees
Sep 2 - Sep 3
Farmhouse in Chianti
Outdoor dining

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

Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi
BARBERINO TAVARNELLE
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 ￥49,474
￥59,489 total
includes taxes & fees
Sep 2 - Sep 3
Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi
Dining

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

Holiday Home 'Poggio Loccano' with Private Garden and Balcony
Montevarchi
The price is ￥35,052
￥53,598 total
includes taxes & fees
Sep 6 - Sep 7
Holiday Home 'Poggio Loccano' with Private Garden and Balcony
Pool

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

Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
The price is ￥26,706
￥27,077 total
includes taxes & fees
Sep 1 - Sep 2
Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
Pool

18. Casale Rosennano Apartment – Shared Garden, Wi-Fi, Medieval Setting

Casale Rosennano Apartment – Shared Garden, Wi-Fi, Medieval Setting
Rosennano
The price is ￥44,640
￥45,383 total
includes taxes & fees
Aug 31 - Sep 1
Casale Rosennano Apartment – Shared Garden, Wi-Fi, Medieval Setting
Pool

19. 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)
The price is ￥56,751
￥68,621 total
includes taxes & fees
Aug 30 - Aug 31
Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi
Interior

20. Little cozy house

Little cozy house
Loro Ciuffenna
The price is ￥12,982
￥16,320 total
includes taxes & fees
Sep 2 - Sep 3
Little cozy house
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

Villa Sabolini

Villa Sabolini

10/10 Excellent
"We couldn’t rate Villa Sabolini more highly - we had such an excellent time. It is a beautiful property and the perfect place to relax and enjoy Tuscany. The staff were so helpful and friendly too."
Andrew 5-night trip
Posted 2 hours ago
Villa Sabolini

Find out more about Chianti Region

Chianti Region Vacation Homes information

Number of reviews
244
Accommodation
417 Vacation Homes
Lowest Price
￥16,320
Highest Price
￥96,996

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