Chianti Region Romantic Vacations 2026

Plan, book, travel with confidence
Better together
Save up to ￥109,000 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

Romance awaits at this villa, which features a garden and a hot tub. Couples will appreciate the in-room fireplaces and outdoor pool.

10/10 Exceptional! (122 reviews)

Couples like: hot tub, fireplace

Travelers say...

"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 Jul 25, 2026

Palazzo Leopoldo Dimora Storica & Spa

Via Roma 33 Radda in Chianti SI

35 min drive from Antinori nel Chianti Classico

Book a stay at this romantic hotel, featuring a spa and in-room massages. Couples will appreciate the hot tub, al fresco dining, and wine tasting rooms.

9.2/10 Wonderful! (302 reviews)

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

Travelers say...

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

Reviewed on Sep 28, 2026

COMO Castello Del Nero

Strada Spicciano 7 Barberino Tavarnelle FI

10 min drive from Antinori nel Chianti Classico

For a romantic stay, consider this upscale hotel, featuring a spa, a Michelin star restaurant, and a garden. Couples will appreciate the hot tub and Egyptian ...

9.6/10 Exceptional! (145 reviews)

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

Travelers 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 Sep 11, 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.