Cheap Vacations in Chianti Region 2026

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Flight and Cheap hotel deals in Chianti Region

Price found within the past 48 hours. Click for updated prices.

Park Hotel Chianti

Tavarnelle Val di Pesa

CA $1,008

per person

Nov 27 - Dec 3

found 1 day ago

Roundtrip flight included

Montreal (YUL) to Florence (FLR)

9/10 Wonderful! (276 reviews)

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Cheap Hotels in Chianti Region

Ostello del Chianti

Via Roma 137 Barberino Tavarnelle FI

16 min drive from Tenuta Torciano Winery

Stay at this hostel in Barberino Tavarnelle. Enjoy free parking, breakfast (surcharge), and daily housekeeping. Popular attractions Castello di Barberino Val ...

8.6/10 Excellent! (9 reviews)

A good stop in Chianti

"Basic but good hostel. The position is on the way to Siena from Florence. Perfect to explore Chianti. The free parking is a bonus for the ones who travel by car"

Reviewed on Aug 13, 2021

Cosy apartment in villa with pool, WIFI, TV, patio and panoramic view, close to San Gimignano

Poggibonsi Tuscany

15 min drive from Tenuta Torciano Winery

Stay at this villa in Poggibonsi. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the overall value in our reviews. Popular attractions ...

8.8/10 Excellent! (40 reviews)

Review for stay from 14 August 2026 to 21 August 2026

"Lieu délicieux, plein de charme et de poésie, très bien situé. Piscine très agréable, literies parfaites et belles chambres. Salle de séjour très moyenne (assez sombre et pourtant chaude) mais on peut prendre ses repas dehors à condition de descendre une volée de marches. Quelques détails pourraient ..."

Reviewed on Aug 28, 2026

See all 4,811 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.