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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

Stay at this family-friendly villa in San Gimignano. Enjoy free Wi-Fi, private pools and a fitness centre. Popular attractions Fonti Medievali and Archaeological ...

10/10 Exceptional! (71 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 spa hotel in Radda in Chianti. Enjoy free Wi-Fi, free parking and a full-service spa. Popular attractions Castello di Radda Winery and Volpaia are ...

9.2/10 Wonderful! (273 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 luxury hotel in Barberino Tavarnelle. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Abbey of Passignano and Casa Sola - ...

9.4/10 Exceptional! (132 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 4,765 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.