Castellina in Chianti Hotel Alternatives

We selected the 2714 homes worth renting in this location

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Home spotlights in Castellina in Chianti

Vineyards & Red Earth

Vineyards & Red Earth

  • 8 guests

  • 3 bedrooms

Barberino Tavarnelle, Florence

Once owned by winemaker Marchesi Torrigiani, this beautiful hillside villa still features the vineyards that were once, and will likely always be, the heart of this farmland. A beautiful sight, it’s only marginally rivalled by the view of the Chianti Hills which is sprawled out right before you from the elevated position of this home.

First Of The Summer Wine

First Of The Summer Wine

  • 6 guests

  • 4 bedrooms

Castellina in Chianti, Tuscany

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 interior, where farmhouse simplicity meets elegant design in the living room.

Sweet Tuscany

Sweet Tuscany

  • 2 guests

  • 1 bedrooms

Gaiole in Chianti, Siena

Tailor-made for two, this charming villa promises a tranquil escape in the Tuscan countryside. We love the character-packed interiors, where you’ll find everything needed to kick back and relax.

The Olive Tint

The Olive Tint

  • 8 guests

  • 4 bedrooms

Radda in Chianti, Tuscany

Overlooking the Tuscan countryside from its hillside position, this rustic villa boasts some incredible views – best celebrated from the outside dining area and elegant infinity pool. We think it's a great fit for families with a lovely private garden as well as flexible sleeping arrangements – the twin beds can be converted into doubles upon request.


We selected the top 3% holiday homes in Castellina in Chianti Hotel Alternatives

Explore the 2714 most perfect homes in our collection

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Most popular homes in Castellina in Chianti

Dreaming of Chianti

Dreaming of Chianti

  • 6 guests

  • 3 bedrooms

Castellina in Chianti, Tuscany

Over the Chianti Hills

Over the Chianti Hills

  • 4 guests

  • 1 bedrooms

Barberino Tavarnelle, Florence

The Tuscan Muse

The Tuscan Muse

  • 14 guests

  • 7 bedrooms

Tregole, Tuscany

The Rosso

The Rosso

  • 8 guests

  • 4 bedrooms

Radda in Chianti, Tuscany

Vineyard Sunset

Vineyard Sunset

  • 6 guests

  • 3 bedrooms

Radda in Chianti, Tuscany

Chianti Rosemary

Chianti Rosemary

  • 4 guests

  • 2 bedrooms

Castellina in Chianti, Tuscany

The Papessa

The Papessa

  • 6 guests

  • 2 bedrooms

Barberino Tavarnelle, Florence

The Olive Stone

The Olive Stone

  • 6 guests

  • 3 bedrooms

Gaiole in Chianti, Siena

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Frequently asked questions

Looking for alternatives to overpriced, cramped hotels in Castellina in Chianti, Siena, Tuscany, Italy? You've come to the right place: we’ve cherry-picked a selection of hotel alternatives which offer better value, more space, more privacy and more flexibility. Our vetted homes are located in central, vibrant neighbourhoods. 100% ready for living and available for short or extended stays.

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