Castiglion Fiorentino

Travel Guide

A historic town with a prominent church tower, surrounded by rolling hills and vineyards.
A rural landscape with fields, trees, and mountains under a partly cloudy sky.
A panoramic view of a valley with a wooden fence in the foreground, dense green foliage, and distant hills under a clear sky.
Photo by Pigellino (Creative Commons Attribution 3.0)
A sunflower field with a town in the background.
Photo by Pigellino (Creative Commons Attribution 3.0)
A dirt path leading to a panoramic view of a valley with scattered buildings and fields.
Photo by Pigellino (Creative Commons Attribution 3.0)
Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

5 out of 5
Localita Piazzano, C.P. 6 Cortona AR
Fully refundableReserve now, pay when you stay
The price is S$913 per night from 14 Oct to 15 Oct
S$913
14 Oct - 15 Oct
includes taxes & fees
Stay at this luxury hotel in Cortona. Enjoy free Wi-Fi, free parking and room service. Our guests praise the helpful staff in their reviews. Popular attractions ...
9.8/10 Exceptional! (251 reviews)
"Stunning little hotel with the most beautiful setting, gardens and pool. The room was exceptionally appointed clean. The best part of the stay was the restaurant. The best meals we had on our entire trip. Definitely recommend hiring e-bikes and riding up to Cortona!"

Reviewed on 20 Sept, 2026

Villa di Piazzano - Small Luxury Hotel of the World
Nuovo Etruria Resort

Nuovo Etruria Resort

Via di S. Martino snc Montepulciano SI
The price is S$176 per night from 30 Sept to 1 Oct
S$176
30 Sept - 1 Oct
includes taxes & fees
Stay at this hotel in Montepulciano. Enjoy an outdoor pool, breakfast (surcharge) and daily housekeeping. Popular attractions Colonna del Marzocco and Palazzo ...
Nuovo Etruria Resort
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Di Poggio Alla Sala, 10 Montepulciano SI
The price is S$844 per night from 7 Oct to 8 Oct
S$844
7 Oct - 8 Oct
includes taxes & fees
Stay at this luxury hotel in Montepulciano. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular ...
9.6/10 Exceptional! (173 reviews)
"Great location, nice vineyards right out the door, lots of great restaurants nearby."

Reviewed on 25 Sept, 2026

Precise Tale Poggio Alla Sala
See all 6,563 properties in Castiglion Fiorentino
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.
Hotel San Gregorio

Hotel San Gregorio

3 out of 5
Via Della Madonnina 4 Pienza SI
Stay at this business-friendly residence in Pienza. Enjoy free Wi-Fi, an outdoor pool and room service. Popular attractions Enoteca Di Ghino and Artemisia Gallery ...
9.4/10 Exceptional! (157 reviews)
"Quaint but modern hotel walking distance to all - good breakfast and service in hotel restaurant. Spacious rooms with air conditioning (which gets turned off when staff cleans room - call desk to turn back on), safe, and bathroom with tub- but no shower curtain- took a while to learn how to negotiate ..."

Reviewed on 17 Sept, 2026

Hotel San Gregorio
Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites

3 out of 5
Strada Provinciale 146 di Chianciano San Quirico d'Orcia SI
Stay at this residence in San Quirico d'Orcia. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Popular attractions Horti Leonini and Chapel of our Lady ...
9.2/10 Wonderful! (97 reviews)
"The room snd entire property were spotless clean. Staff wete helpful and friendly. Our room and patio overlooked the d'Orcia valley, gorgeous any time, especially in the morning. The entire grounds, pool, loungers, plants were well maintained. This was our third time at Cassanova and we would come ..."

Reviewed on 25 Sept, 2026

Casanova - Panoramic Rooms and Suites
Abbadia Sicille Relais

Abbadia Sicille Relais

4 out of 5
SP 14 Loc. Abbadia Sicille Trequanda SI
Stay at this business-friendly residence in Trequanda. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions San Giovanni d'Asso Station and ...
Abbadia Sicille Relais
See all properties in Castiglion Fiorentino
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.

Stay near popular Castiglion Fiorentino attractions

Tennis Club Castiglionese

Catch an event at Tennis Club Castiglionese during your trip to Castiglion Fiorentino. You can enjoy the wineries while in the area.
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Things to do

Oil museum and oil mill in Tuscany: tour and tasting

Oil museum and oil mill in Tuscany: tour and tasting

S$29
per adult
Oil museum and oil mill in Tuscany: tour and tasting
Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

S$37
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
Tasting with Private Walk in a Cellar in Tuscany

Tasting with Private Walk in a Cellar in Tuscany

S$37
per adult
Tasting with Private Walk in a Cellar in Tuscany
Arezzo Gran Tour

Arezzo Gran Tour

S$18
per adult
Arezzo Gran Tour
2-Hour Private Wine Tasting in the Cellar in Mugliano

Private Tasting of Organic Wines in the Cellar in Mugliano

S$44
per adult
Private Tasting of Organic Wines in the Cellar in Mugliano
Arezzo: Val di Chiana Wine Tasting Experience

Arezzo: Val di Chiana Wine Tasting Experience

S$58
per adult
Arezzo: Val di Chiana Wine Tasting Experience
See all activities in Castiglion Fiorentino
A historic square with a prominent tower, a church with a bell tower, and a café area.

Arezzo

A historic building with a red and white striped flag, brick walls, and a staircase leading to an entrance.

Foiano della Chiana