Top Romantic Chianti Region Hotels

VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN-SUITE BEDROOMS, SWIMMING POOL, SPA, SAUNA.

San Gimignano

29 min drive from Antinori nel Chianti Classico

Book a stay at this family-friendly villa in San Gimignano. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Fonti Medievali and Archaeological ...

10/10 Exceptional! (70 reviews)

The property is beautiful and very well taken care of. Loved the location and how wonderful the owners were to help with organizing drivers, chef, and other needs. Would highly recommend and will definitely be back. Very special experience.

Reviewed on 26 Oct 2025

Palazzo Leopoldo Dimora Storica & Spa

Via Roma 33, Radda in Chianti, SI

35 min drive from Antinori nel Chianti Classico

Stay at this 4-star spa hotel in Radda in Chianti. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Castello di Radda Winery and Borgo ...

9.2/10 Wonderful! (270 reviews)

Excellent breakfast.

Reviewed on 30 Sept 2025

COMO Castello Del Nero

Strada Spicciano 7, Barberino Tavarnelle, FI

10 min drive from Antinori nel Chianti Classico

Stay at this 5-star luxury hotel in Barberino Tavarnelle. Enjoy free WiFi, free parking, and private pools. Popular attractions Abbey of Passignano and Casa ...

9.4/10 Exceptional! (130 reviews)

Wonderful stay. 5-stars across the board if you’re looking for disconnecting and relaxing in the rolling hills of the Tuscan countryside. Easy day/dinner trips to Florence or Siena (rental car).

Reviewed on 25 Oct 2025

See all 4,933 properties in Chianti Region

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.