Chianti Region Romantic Vacations
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Top Romantic Chianti Region Hotels
VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN SUITE ROOMS, SWIMMING POOL, SPA, SAUNA.
San Gimignano
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! (68 reviews)
Couples like: hot tub, fireplace
Tuscany stay
"It is a wonderful property, a beautiful villa with all expectations met, Caterina and Calorina were great hosts and looked after every detail. Location was great right in the middle of wine country"
Reviewed on Jun 14, 2025
Palazzo Leopoldo Dimora Storica & Spa
Via Roma 33, Radda in Chianti, SI
Book a stay at this romantic hotel, featuring a spa and in-room massages. Couples will appreciate the hot tub, al fresco dining, and garden.
9.2/10 Wonderful! (261 reviews)
Couples like: full-service spa, couples spa treatments, al fresco dining, hot tub
Travelers say...
"A place to stay where you can’t go wrong. Relaxing with lots of activities nearby"
Reviewed on Jun 28, 2025
COMO Castello Del Nero
Strada Spicciano 7, Barberino Tavarnelle, FI
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 ...
9.4/10 Exceptional! (123 reviews)
Couples like: full-service spa, couples spa treatments, Michelin star restaurant, hot tub
Travelers say...
"Fantastic staff, warm but professional! Great recs and helped with booking good transport. Breakfast was the best I had in Europe! Amazing views"
Reviewed on May 13, 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.