5-Star Luxury Rentals Castellina in Chianti

Grapevine Dreams
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Grapevine Dreams

Castellina in Chianti, Tuscany, Italy
18 guests
8 bedrooms
This villa sits on a wine estate in the Chianti Hills, where the vines have been owned and tended to by the same family since 1865. If you’re not exploring the rolling, vine-clad hills of the grounds,.....
From €1,227
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The Valley
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The Valley

Castellina in Chianti, Tuscany, Italy
9 guests
5 bedrooms
You can arrive in style at this palatial farmhouse fringing the hilltop commune of Castellina (2.7km) - there's a private helipad should you need it. Set within easy driving distance of Siena, San Gim.....
From €789
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Cheers to Chianti
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Cheers to Chianti

Castellina in Chianti, Tuscany, Italy
3 guests
2 bedrooms
You've got all the perks of a private home combined with the palatial shared grounds of a hamlet at this apartment complex nestled between the Chianti villages of Panzano and Castellina. The views of.....
From €337
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First Of The Summer Wine
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First Of The Summer Wine

Castellina in Chianti, Tuscany, Italy
6 guests
4 bedrooms
Surrounded by olive trees and vast swathes of vineyards, this Tuscan home in the heart of the Chianti wine region is a haven of rural relaxation. Its exposed stone exterior gives way to a bright inter.....
From €1,307
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Tuscan Orgins
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Tuscan Orgins

Castellina in Chianti, Tuscany, Italy
10 guests
5 bedrooms
From the countryside views to the traditional character inside, there's no denying that this home is unmistakably Tuscan. It's situated among a working vineyard, offering access to the estate's commun.....
From €448
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The Stuff of Dreams
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The Stuff of Dreams

Castellina in Chianti, Tuscany, Italy
10 guests
5 bedrooms
With a truly picturesque location in the Chianti hills, this rustic villa is the ideal choice for anybody that has fantasised at any point about eloping to Tuscany for a short while — which is surely.....
From €502
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A Taste of the Hills
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A Taste of the Hills

Castellina in Chianti, Tuscany, Italy
2 guests
1 bedroom
Cosy and quaint, this typically Tuscan apartment is part of a pretty collection of homes, all set inside some historic stone buildings that feel charming and characterful. As such, you'll find terraco.....
From €169
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A Little Bit of Chianti
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A Little Bit of Chianti

Castellina in Chianti, Tuscany, Italy
4 guests
2 bedrooms
This stone-built villa in the heart of Chianti boasts stunning views of the valley and vine-clad hillsides from almost every room. Perfect for two couples wanting to holiday together without crowding.....
From €536
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Grape Juice
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Grape Juice

Castellina in Chianti, Tuscany, Italy
5 guests
2 bedrooms
Situated on the first floor of a traditional Tuscan stone building, this apartment puts you right at the heart of rural Tuscany, surrounded by glorious rosemary bushes, grape vineyards and olive grove.....
From €311
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Chianti Dreamers
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Chianti Dreamers

Castellina in Chianti, Tuscany, Italy
6 guests
2 bedrooms
This apartment is a comfortable base from which to explore all that Tuscany has to offer. Siena, around 27 kilometres away, is an ideal day trip destination, while the small town of Castellina in Chia.....
From €273
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Chianti Rosemary
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Chianti Rosemary

Castellina in Chianti, Tuscany, Italy
4 guests
2 bedrooms
Sitting on the hillside in Chianti's countryside, this apartment is part of a small collection of cottages and apartments. Typically Tuscan, the interior may be a tad dated – and you'll have to share.....
From €261
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Dreaming of Chianti
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Dreaming of Chianti

Castellina in Chianti, Tuscany, Italy
6 guests
3 bedrooms
After a day touring world-class vineyards, this home is the perfect place to unwind with a glass of Chianti. Sure, there’s no air conditioning here, and the traditional interiors may not be to everyon.....
From €340
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Brick & Green Shutters
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Brick & Green Shutters

Castellina in Chianti, Tuscany, Italy
6 guests
3 bedrooms
There are many great things to say about this 18th century villa in Chianti, so let’s start with the most obvious, shall we? Overlooking the breathtaking Chianti Classico hills, the view here is somet.....
From €477
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A Touch of Chianti
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A Touch of Chianti

Castellina in Chianti, Tuscany, Italy
8 guests
4 bedrooms
Stylishly rustic, this country home sets the tone for a restorative retreat in the heart of Chianti. Dating back to the 10th century, the house has a wonderful sense of character with plenty of space.....
From €1,700
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Wild Grapes
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Wild Grapes

Castellina in Chianti, Tuscany, Italy
4 guests
2 bedrooms
If you're coming to Chianti to sample its most famous product, you've hit the jackpot with this beautiful villa set on a wine estate. Just a few hundred metres from the cellars and wine shop, you'll b.....
From €471
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Il Nocino
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Il Nocino

Castellina in Chianti, Tuscany, Italy
8 guests
4 bedrooms
This charming cottage is tucked away on an authentic working vineyard, beside a family farmhouse. It’s just 1 kilometre from Castellina in Chianti, and within driving distance of Sam Gimignano, Siena,.....
From €422
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