Self-Catering Gaiole in Chianti, Tuscany

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The Olive Stone

Tuscany, Gaiole in Chianti 6 guests 3 bedrooms 3 bathrooms Enjoying a secluded spot in the Chianti countryside, this traditional stone villa is packed with things to keep you entertained. The gardens are a delight, where olive groves provide a spot for a shad... From €1,076 Nightly View Rental

The Hillside Sanctuary

Tuscany, Gaiole in Chianti 2 guests 1 bedroom 1 bathroom Housed in a restored stone barn, this cottage places you in the heart of Chianti with views of rolling fields, vineyards and valleys as far as the eye can see. The home benefits from a beautifully ele... From €267 Nightly View Rental

Toscana Per Sempre

Tuscany, Gaiole in Chianti 2 guests 1 bedroom 1 bathroom Housed within a complex of stone buildings that were once a wine and olive oil-producing estate, this home offers Tuscan relaxation in spades. A communal pool, children’s pool and tennis courts await... From €174 Nightly View Rental

Hillside Harvest

Tuscany, Gaiole in Chianti 4 guests 2 bedrooms 2 bathrooms Nestled on a hilltop estate surrounded by vineyards, this home is one of six on the site of a former medieval castle. You'll share access to the grounds and swimming pool with other guests, but there'... From €284 Nightly View Rental

The Vines of the Vineyard

Tuscany, Gaiole in Chianti 2 guests 2 bedrooms 1 bathroom Lounge by the lavender-edged 18-metre lap pool with its beautiful views of the forested hills and distant hilltop village of Castagnoli. You can’t see the pool from the house, as it's 70 metres down a... From €318 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 €354 Nightly View Rental

Tuscan Gaze

Tuscany, Gaiole in Chianti 10 guests 5 bedrooms 5 bathrooms Nestled in the heart of the Chianti Classico region, this restored Tuscan farmhouse promises an idyllic escape. Sure, the traditional interiors may not be to everyone’s taste, but this home has all th... From €1,173 Nightly View Rental

Chianti Belle

Tuscany, Gaiole in Chianti 8 guests 4 bedrooms 4 bathrooms This 17th-century villa in the heart of the Chianti countryside offers far-reaching views across the vineyards and olive groves out to Siena. You're within walking distance of Lecchi, as well as being... From €617 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 €838 Nightly View Rental

Ivy & Olive

Tuscany, Gaiole in Chianti 8 guests 4 bedrooms 2 bathrooms Calling all wine connoisseurs – this villa puts Chianti's vineyards at your fingertips. Whether you're touring local wineries or day-tripping to the towns of Radda and Siena, this is a picture-perfect... From €445 Nightly View Rental
Self-Catering Gaiole in Chianti
Listing 31-40 of 64 Top Holiday Rentals
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