Hillside Harvest
4 guests
2 bedrooms
Gaiole in Chianti, Siena
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's a private patio where you can enjoy an alfresco glass of wine.
Toscana Per Sempre
2 guests
1 bedrooms
Gaiole in Chianti, Siena
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 in the shared grounds, while the private terrace with its countryside views is perfect for a celebratory sundowner after a day of fun and exploring.
Tuscan Cottage
2 guests
1 bedrooms
Radda in Chianti, Tuscany
This beautifully restored and furnished Tuscan home is the true epitome of an Italian cottage done right. Right in the heart of the Chianti countryside, with the iconically distinctive cypress trees all around, this is the perfect haven for honeymooners looking for a romantic getaway or a solo tripper after a comfortable home close to Florence.
Explore the 114 most perfect homes in our collection
Discover our curated collection of luxury holiday Cottages in Gaiole 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 Gaiole 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.
