Chianti Region Romantic Holidays
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Top Romantic Chianti Region Hotels
VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN SUITE ROOMS, SWIMMING POOL, SPA, SAUNA.
San Gimignano
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! (69 reviews)
Amazing Property and Hosts!
"This is my first time staying in Italy and San Gimignano. The listing of the property is accurate and everything was very clean and well maintained. The hosts Gabriel,, and rest of the team are exceptional with quick responses and clear communication. Our party had four adults and three children ..."
Reviewed on 10 Aug. 2025
Palazzo Leopoldo Dimora Storica & Spa
Via Roma 33, Radda in Chianti, SI
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! (265 reviews)
"We loved it was easy to get to wineries or small towns we wanted to visit"
Reviewed on 11 Jul. 2025
COMO Castello Del Nero
Strada Spicciano 7, Barberino Tavarnelle, FI
Stay at this 5-star luxury hotel in Barberino Tavarnelle. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Abbey of Passignano and Casa ...
9.4/10 Exceptional! (127 reviews)
"Beautiful!"
Reviewed on 2 Aug. 2025
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.