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)
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Poggio alla Sala 10 Montepulciano SI
$532 nightly
The price is $592 total per night from Aug 5 to Aug 6
$592 total
Aug 5 - Aug 6
Total with taxes and fees
Book a stay at this luxury hotel in Montepulciano. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.6/10 Exceptional! (148 reviews)
"It’s a beautiful property, but be aware that it is secluded and that the restaurant menu is quite limited and after a couple of days, we were happy to go elsewhere. The waiting staff was attentive and nice, front desk not as much (maybe the la guard barrier?)"

Reviewed on Jun 19, 2026

Precise Tale Poggio Alla Sala
A Point Arezzo Park Hotel

A Point Arezzo Park Hotel

4 out of 5
Loc. Battifolle, 36/T Arezzo AR
$92 nightly
The price is $108 total per night from Jul 13 to Jul 14
$108 total
Jul 13 - Jul 14
Total with taxes and fees
Book a stay at this spa hotel in Arezzo. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Arezzo Equestrian Centre and Memorial of the ...
7.6/10 Good! (165 reviews)
"Well, having travelled extensively for the past 13 years, this Hotel must be the coldest I have ever stayed in. It was December, but there was no heating on in the lobby area or the dining area so everyone had to wear coats or thick jumpers while eating their meals. The showers were not particularly ..."

Reviewed on Dec 3, 2025

A Point Arezzo Park Hotel
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
$618 nightly
The price is $689 total per night from Jul 20 to Jul 21
$689 total
Jul 20 - Jul 21
Total with taxes and fees
Book a stay at this luxury hotel in Cortona. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
9.8/10 Exceptional! (240 reviews)
"10/10"

Reviewed on Jul 7, 2026

Villa di Piazzano - Small Luxury Hotel of the World
See all 6,613 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.
Spacious Tuscan Villa with Large Pool near Castiglion Fiorentino.

Spacious Tuscan Villa with Large Pool near Castiglion Fiorentino.

Castiglion Fiorentino
Stay at this villa in Castiglion Fiorentino. Enjoy private pools, a garden, and laundry facilities. Popular attractions Agricola Buccelletti Winery and Tennis ...
9.8/10 Exceptional! (42 reviews)
"We are a family of 6. We were traveling throughout Italy, Switzerland, and France. We choose this property for a few relaxing days in Tuscany. It did not disappoint. The property, hosts, scenery, and pool are amazing. It was pretty hot when we stayed in June and we absolutely loved relaxing at the ..."

Reviewed on Jul 6, 2026

Spacious Tuscan Villa with Large Pool near Castiglion Fiorentino.
Lovely home in Castiglion Fiorentino

Lovely home in Castiglion Fiorentino

Castiglion Fiorentino
Stay at this vacation home in Castiglion Fiorentino. Enjoy free WiFi, private pools, and a sauna. Popular attractions Cassero Tower and Archaeological Museum ...
Lovely home in Castiglion Fiorentino
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 WiFi, and an outdoor pool. Popular attractions Horti Leonini and Chapel of our Lady ...
9.2/10 Wonderful! (92 reviews)
"Our stay at Casanova Panoramic Rooms was absolutely wonderful. The room was beautiful, spotless, and the view was simply breathtaking. The entire check-in process was smooth and welcoming, and having convenient parking made everything even easier. We also loved the restaurant—the food was delicious, ..."

Reviewed on Jul 7, 2026

Casanova - Panoramic Rooms and Suites
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.
See properties

Things to do

Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

$29
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
Cellar Tour & Wine Tasting

Cellar Tour & Wine Tasting

$57
per adult
Cellar Tour & Wine Tasting
Arezzo: Val di Chiana Wine Tasting Experience

Arezzo: Val di Chiana Wine Tasting Experience

$46
per adult
Arezzo: Val di Chiana Wine Tasting Experience
See all activities in Castiglion Fiorentino

Cities near Castiglion Fiorentino

A historic square with a central open space, surrounded by colorful buildings with arched windows and a prominent tower.

Arezzo

A hillside town with historic buildings, a church, and vineyards.

Cortona

A stone tower, a curved road, and traditional buildings with a stone wall.

Monte San Savino

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

Foiano della Chiana

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