Chianti Region Vacation Homes

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 holiday 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

HK$1,438 total

includes taxes & fees

16 Sept - 17 Sept

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.

HK$1,658 total

includes taxes & fees

24 Sept - 25 Sept

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

3. House with views of the Chianti

impruneta

Chase B.

HK$2,084 total

includes taxes & fees

27 Sept - 28 Sept

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

4. Wonderful Tuscan farmhouse with large spaces and panoramic views

impruneta

Christine F.

HK$2,320 total

includes taxes & fees

28 Sept - 29 Sept

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

5. 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.

HK$3,742 total

includes taxes & fees

14 Oct - 15 Oct

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

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

Greve in Chianti

Linda L.

HK$3,162 total

includes taxes & fees

15 Oct - 16 Oct

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

7. Casa Marisa in Castellina in Chianti

Castellina in Chianti

HK$2,446 total

includes taxes & fees

20 Sept - 21 Sept

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

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

Figline Valdarno

HK$951 total

includes taxes & fees

12 Oct - 13 Oct

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Top Chianti Region Hotel Reviews

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"The experience was exceptional, the dinners in both restaurants on site were spectacular. The staff was amazing, friendly, and made our stay very memorable. We are planning to return soon."

Fattoria di Vegi

10/10 Excellent

"This place is a little piece of heaven on earth. If you are looking for peace, tranquility, beautiful surroundings, luxurious rooms, friendly hand helpful staff, this is the place for you. We have stayed in many luxurious places, but this hotel we both thought was the best we have ever experienced. It had a homely feel, you felt part of the family. In each block there was a lounge, so it felt like a home. And an honesty box for the bar and drinks at the pool, again making it feel like a home where you help yourself. The food in the restaurant was delicious, the wine tasting tour was really good with Ingrid who was lovely, I honestly can’t rate this place highly enough. If you wish for a few days of luxury and tranquility, make a booking, you won’t regret it."

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