Chianti Region Romantic Holidays 2026

Plan, book, travel with confidence
Better together
Save up to NZ$2,400 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

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! (302 reviews)

"Amazing historical hotel in a beautiful town, 10 out of 10."

Reviewed on 28 Sept 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 Castello di Barberino Val d'Elsa and ...

9.6/10 Exceptional! (145 reviews)

"The most beautiful hotel in the heart of Chianti. The service was above and beyond. Everything about this charming hotel was amazing. We cannot wait to go back."

Reviewed on 11 Sept 2026

See all 4,909 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.