Chianti Region Romantic Holidays 2026

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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! (122 reviews)

"My family of 10, 2 grandparents, two adult children and their spouses plus 4 teenagers spent a wonderful week at that the Villa Iris. The house is lovely and has air conditioning. The 6 bedrooms with 6 bathrooms were great to have. Every day we went went to a different hill town, explored them and ..."

Reviewed on 25 July 2026

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 2 indoor pools. Popular attractions Castello di Radda Winery and Volpaia are located ...

9.2/10 Wonderful! (296 reviews)

"Very helpful and friendly staff, beautiful and spacious room, and wonderful location in the most lovely town in Tuscany. We loved our stay!"

Reviewed on 14 Aug 2026

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 Antinori nel Chianti Classico and Castello ...

9.6/10 Exceptional! (142 reviews)

"Great staff!"

Reviewed on 27 June 2026

See all 4,898 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.