Rent Luxury Holiday Cottages in Castellina in Chianti

We selected the 114 homes worth renting in this location

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Home spotlights in Castellina in Chianti

Il Nocino

Il Nocino

  • 8 guests

  • 4 bedrooms

Castellina in Chianti, Tuscany

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, and Florence – you’ll have plenty of options for day trips.

Chianti Memories

Chianti Memories

  • 10 guests

  • 5 bedrooms

Radda in Chianti, Tuscany

With rolling Chianti hills all around, this traditional villa couldn't feel more Tuscan if it tried. Comprised of a main house and three en-suite bedroom cottages, it's perfect for a large family getaway.

The Etruscan View

The Etruscan View

  • 4 guests

  • 2 bedrooms

Galenda, Gaiole in Chianti

Escape to the tranquillity of the Tuscan hills when you stay at this two-bedroom home. Inside, the rooms are simply styled with country character, including a cosy living space and a homely kitchen.

Chianti Sunrise

Chianti Sunrise

  • 4 guests

  • 2 bedrooms

Castelnuovo Berardenga, Siena

Nestled in a private estate overlooking the Chianti hills, this cottage sets the tone for a magical Italian stay. There’s a private terrace and outdoor seating for alfresco dining, while the rooms make it easy to switch off and unwind.

We selected the top 3% holiday homes in Castellina in Chianti Cottages

Explore the 114 most perfect homes in our collection

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Most popular homes in Castellina in Chianti

Cheers to Chianti

Cheers to Chianti

  • 3 guests

  • 2 bedrooms

Castellina in Chianti, Tuscany

Hillside Harvest

Hillside Harvest

  • 4 guests

  • 2 bedrooms

Gaiole in Chianti, Siena

Toscana Per Sempre

Toscana Per Sempre

  • 2 guests

  • 1 bedrooms

Gaiole in Chianti, Siena

A Little Bit of Chianti

A Little Bit of Chianti

  • 4 guests

  • 2 bedrooms

Castellina in Chianti, Tuscany

Tuscan Cypresses

Tuscan Cypresses

  • 10 guests

  • 7 bedrooms

Castelnuovo Berardenga, Siena

Tower Of Vines

Tower Of Vines

  • 10 guests

  • 5 bedrooms

Tignano, Barberino Tavarnelle

Picturesque Embrace

Picturesque Embrace

  • 4 guests

  • 2 bedrooms

Castellina in Chianti, Tuscany

Tuscan Flow

Tuscan Flow

  • 4 guests

  • 2 bedrooms

Castelnuovo Berardenga, Siena

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Frequently asked questions

Discover our curated collection of luxury holiday Cottages in Castellina in Chianti, Siena, Tuscany, Italy. We painstakingly review all homes available in a destination and accept only the top 3% to ensure quality our guests can trust. Each of the Castellina in Chianti Cottages in our collection comes fully furnished with essential bathroom toiletries, expertly-equipped kitchens and all linens included. Book your dream stay today and should you need some help, our friendly team of experts are on hand to help plan your perfect Cottage break.

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