Castellina in Chianti Summer Rentals, Cottages & Cabins

There are a lot of options in Castellina in Chianti. If you plan on staying in the Castellina in Chianti area, consider making a reservation for a few nights at one of these properties as these have been rated the top Summer Rentals in Castellina in Chianti:

• Single-level Villa, panoramic position, AC, 6x16m private Pool, Whirlpool & Spa
• Castello La Leccia
• Beautiful house on Chianti hilltop with exceptional views.
• Belvedere 2+1 BR Luxe Apart In a Restored Tuscan Farm with Pool and Spa
• La Torre Beautiful 1BR Love Nest In a Restored Farm. Pool, spa private terrace
• Forno 1BR Apartment In a Restored Farm, Pool & Spa, 1st floor, 140/190cm sofabed
• Podere La Valle 9BR, 16-20 Guests Retreats & Family In Restored Farm Spa & Pool
• Roccia 2BR apart PRM OK in restored Farm w Pool and Spa, ground floor terrace
• Arco : 2BR apart in a restored Farm w Pool and Spa, ground floor terrace
• Charming Chianti hilltop house, exceptional views, large swimming pool

In 2026, Mydreamydestination offers 384 summer rentals in or around Castellina in Chianti. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.

The average price per night for a summer rental in Castellina in Chianti is $523. Check the full list of summer accommodations in Castellina in Chianti.

There are 384 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Mydreamydestination.

Yes, here are some popular summer holiday rentals in Castellina in Chianti that have a private or indoor pool:

• House with swimming pool. Medieval village in the heart of Chianti Classico
• Strada di Tregole Cottage
• Borgo Sicelle
• Villa with large garden in the Chianti hills

Check all holiday rentals with a pool in Castellina in Chianti on Mydreamydestination.