Self-Catering Gaiole in Chianti, Tuscany

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Sunflowers & Sangiovese

Tuscany, Gaiole in Chianti 10 guests 4 bedrooms 3 bathrooms Treat yourself to a relaxing stay at this rustic villa in the heart of Chianti, one of the Old World’s best known wine regions. Fully renovated in 2016, this authentic Italian home will delight even t... From €930 Nightly View Rental

Chianti Hilltop

Tuscany, Gaiole in Chianti 6 guests 3 bedrooms 3 bathrooms This beautiful, traditional villa sits in the Chianti countryside between the wine towns of Radda and Gaiole in Chianti. It’s a splendid spot, whether you plan on exploring the local vineyards or just... From €881 Nightly View Rental

From the Hilltop

Tuscany, Gaiole in Chianti 6 guests 4 bedrooms 3 bathrooms This Tuscan villa offers breathtaking views of the surrounding vineyards from its hilltop position. And while the traditional interiors here may not be everyone’s cup of tea, the multiple living space... From €611 Nightly View Rental

Sangiovese Sunset

Tuscany, Gaiole in Chianti 2 guests 1 bedroom 1 bathroom This semi-detached cottage is wrapped in glorious Chianti countryside, making it an ideal base for a relaxing break for two. We love the private hot tub, nestled in a shady spot and perfect for quiet... From €166 Nightly View Rental

Chianti Soul

Tuscany, Gaiole in Chianti 6 guests 3 bedrooms 2 bathrooms This restored two-storey stone-built home has a hillside location, so it has wonderful vistas (just don’t bring your sports car as the access road is very steep). You can enjoy the glorious views from... From €450 Nightly View Rental

The Olive Vine

Tuscany, Gaiole in Chianti 6 guests 3 bedrooms 3 bathrooms Just outside of Gaiole's idyllic town, serving authentic cuisine and Chianti wine, this hillside home offers pastoral vistas. There's an upside-down layout inside, putting the bedrooms below the livin... From €450 Nightly View Rental

Vino on the Terrace

Tuscany, Gaiole in Chianti 4 guests 2 bedrooms 2 bathrooms Part of a 13th-century estate-turned-resort, this apartment makes the most of its scenic location in Chianti. Alongside a private terrace, you'll have access to a communal hilltop swimming pool, share... From €188 Nightly View Rental

The Artist's Cottage

Tuscany, Gaiole in Chianti 6 guests 3 bedrooms 2 bathrooms In the heart of the Chianti hills, this cosy villa offers a tranquil escape. Its compact design belies surprisingly spacious rooms, while the wooden beams sprinkle character over the home. That said,... From €340 Nightly View Rental

I Dream of Chianti

Tuscany, Gaiole in Chianti 10 guests 5 bedrooms 5 bathrooms This former defence watchtower dating back to the 10th century has been beautifully reimagined into a corker of a family home. Within the palatial grounds, there's a ping-pong table, pool table, table... From €1,080 Nightly View Rental

Vines & Serenity

Tuscany, Gaiole in Chianti 4 guests 2 bedrooms 2 bathrooms Wrapped in vineyards and olive groves, this cosy villa in the heart of the Chianti countryside promises a serene escape from daily life. It’s not the biggest inside, but it’s more than comfortable for... From €281 Nightly View Rental
Self-Catering Gaiole in Chianti
Listing 21-30 of 57 Top Holiday Rentals
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