Vineyard Estate
4 guests
2 bedrooms
Castellina in Chianti, Tuscany
Perched on a sun-kissed Chianti hillside, this home offers a quintessential Tuscan escape. Rustic stone walls and terracotta tiles give a traditional feel, while the private terrace is perfect for al fresco dining.
Classic Moments
10 guests
5 bedrooms
Castellina in Chianti, Tuscany
If you’re in search of a rustic retreat in the heart of Chianti Classico, this home delivers a sweet solution. You can enjoy stunning views across olive groves, vineyards and rolling hills.
Being of Beauty
18 guests
9 bedrooms
Lilliano, Castellina in Chianti
Experience the beauty of Chianti with a stay in this luxurious Tuscan retreat. Owned by a family for more than a hundred years, now you’re invited to step inside and make your own special memories.
The Tuscan Muse
14 guests
7 bedrooms
Tregole, Castellina in Chianti
With majestic views across rolling hills and olive groves, this home makes it easy to enjoy the magic of Italy. Set within a working winery, you’ll be treated to an authentic taste of rural life along with all the essentials you could need to slow down and spend quality time together.
Explore the 3890 most perfect homes in our collection
Browse our curated collection of Short Stay Rentals in Castellina in Chianti, Siena, Tuscany, Italy. From impeccable interior design and chef-worthy kitchens, to fully furnished bathrooms and the inclusion of all linens, the homes in our collection come complete with everything you need. Each of the Castellina in Chianti luxury short stay apartments in our collection has been expertly reviewed to ensure the quality standards you can trust, so book today to enjoy a getaway to remember. And should you need any assistance, our friendly team of experts are here to help you find the perfect home.
