Chianti Region Romantic Holidays 2026

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Top Romantic Chianti Region Hotels

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)

Couples like: full-service spa, couples spa treatments, al fresco dining, hot tub

Travellers say...

"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)

Couples like: full-service spa, couples spa treatments, Michelin star restaurant, hot tub

Travellers say...

"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

Villa il Poggiale - Dimora Storica

Via Empolese 69 San Casciano in Val di Pesa FI

10 min drive from Antinori nel Chianti Classico

Stay at this spa property in San Casciano in Val di Pesa. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Monastery of Sorelle Clarisse ...

9.4/10 Exceptional! (158 reviews)

Couples like: on-site spa services, couples spa treatments, al fresco dining, Hot tub

Travellers say...

"Villa il Poggiale is spectacular! It dates from the 1300s; it is not a new cookie cutter hotel. Each room is individually decorated and all of our rooms were well appointed, quiet and maintained. And each has room blackening shutters as well as modern amenities like HVAC and flat screen TVs. Just ..."

Reviewed on 30 Sept 2026

See all 4,903 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.