A historic town with a prominent church tower, surrounded by rolling hills and vineyards.

Find 5 Star Hotels in Castiglion Fiorentino from ￥13,800

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Check availability on Castiglion Fiorentino 5 Star Hotels

Tonight
Sep 30 - Oct 1
Tomorrow
Oct 1 - Oct 2
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Castiglion Fiorentino 5-star hotels

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a stone building in the background.
An outdoor dining area with tables set for a meal, surrounded by greenery and trees.
A hallway with a checkered floor, arched windows, and a chandelier.
A buffet with various food items, a vase of flowers, and a mirror reflecting the room.

1. Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World
Cortona
United Kingdom
Rushab
￥100,678
￥112,173 total
includes taxes & fees
Oct 19 - Oct 20
Villa di Piazzano - Small Luxury Hotel of the World
An aerial view of a large estate with multiple buildings, a swimming pool, and well-maintained gardens.
A spacious dining area with high ceilings and ornate ceiling decorations, featuring multiple tables set for dining.
A large estate with multiple buildings, a swimming pool, and expansive green fields.
A cozy lounge area with a green sofa, a wooden coffee table, wicker chairs, and a view of a lush landscape through an arched doorway.

2. Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala
Montepulciano
United States
Mark
￥93,402
￥103,817 total
includes taxes & fees
Oct 7 - Oct 8
Precise Tale Poggio Alla Sala
A terrace with sun loungers, stone walls, and potted plants.
A pool area with lounge chairs, a hot tub, and a view of mountains.
A narrow hallway with a stone wall and a clock.
A historic town with traditional architecture, a central courtyard with a swimming pool, and a view of distant mountains.

3. Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa
Cortona Old Town
United Kingdom
Alexander
￥42,845
￥48,561 total
includes taxes & fees
Oct 25 - Oct 26
Monastero di Cortona Hotel & Spa
A gazebo with a glass enclosure, surrounded by potted plants and wicker furniture, overlooking a scenic landscape.
A stone building with a red awning, potted plants, and a staircase leading to the entrance.
A person in a swimming pool with a view of trees and mountains through a window.
A person standing at the entrance of a building with a stone staircase leading up to a door.

4. Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux
Cortona
United States
Qingwen
￥59,899
￥67,316 total
includes taxes & fees
Oct 29 - Oct 30
Il Falconiere - Relais e Chateaux
A swimming pool with lounge chairs and a person in a patterned dress.
A stone staircase with candles and a sign reading "CANTINA".
A stone building with a swimming pool, surrounded by a well-maintained garden and a clear sky.
A person performing a yoga pose in a grassy area with a historic building in the background.

5. Castel Monastero - The Leading Hotels of the World

Castel Monastero - The Leading Hotels of the World
Castelnuovo Berardenga
United Kingdom
G
￥87,590
￥98,139 total
includes taxes & fees
Oct 28 - Oct 29
Castel Monastero - The Leading Hotels of the World
A large estate with multiple buildings, a swimming pool, and expansive green fields.
A balcony with a view of a green landscape and a body of water.
A dining area with brick walls, large windows, and a rustic stone ceiling. Tables are set with white tablecloths and candles.
A restaurant with brick arches, white tablecloths, and floral centerpieces.

6. Borgo Sant'Ambrogio Resort

Borgo Sant'Ambrogio Resort
Trequanda
United States
María
￥26,923
￥30,150 total
includes taxes & fees
Oct 13 - Oct 14
Borgo Sant'Ambrogio Resort
A grand banquet hall with ornate ceiling, long tables set for a formal event, and elaborate floral centerpieces.
A long banquet table with gold candelabras, white flowers, and gold tableware.
A large pool with a curved edge, surrounded by a courtyard with a building featuring arched windows and columns.
A historic stone building with arched doorways and a courtyard at twilight.

7. Relais La Corte dei Papi

Relais La Corte dei Papi
Cortona
United Kingdom
Frithjof
￥55,323
￥62,283 total
includes taxes & fees
Oct 26 - Oct 27
Relais La Corte dei Papi
A stone villa with a swimming pool, outdoor seating, and a scenic sunset view.
An open doorway leading to a living room with a sofa, a coffee table, and a lamp.
A large, historic building with multiple wings and a courtyard.
An arched stone corridor leading to a room with a billiards table, a lamp, and a view of the outdoors.

8. Podere Cavalbianco

Podere Cavalbianco
Monte San Savino
United States
Edith
Podere Cavalbianco
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Castiglion Fiorentino.
Hotel Continentale

Hotel Continentale

Piazza Guido Monaco, 7 Arezzo AR
￥19,730
￥23,487 total
Oct 14 - Oct 15
includes taxes & fees
Hotel Continentale
Il Gentiluomo Hotel & SPA

Il Gentiluomo Hotel & SPA

Via Raccordo Autostradale, 1/a Arezzo AR
￥11,569
￥13,800 total
Oct 5 - Oct 6
includes taxes & fees
Il Gentiluomo Hotel & SPA
Relais Cloister Pienza

Relais Cloister Pienza

Corso il Rossellino 26 Pienza SI
￥20,438
￥23,553 total
Oct 29 - Oct 30
includes taxes & fees
Relais Cloister Pienza
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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.

Learn more about Castiglion Fiorentino

Climb the medieval walls of this hilltop town for sweeping views across Tuscany's Val di Chiana countryside. Explore the Etruscan Archaeological Museum inside Palazzo Casali, then enjoy aperitivo with locals in Piazza del Municipio.

See all hotels in Castiglion Fiorentino
A historic town with a prominent church tower, surrounded by rolling hills and vineyards.

Top Castiglion Fiorentino Hotel Reviews

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

10/10 Excellent
"Great location, nice vineyards right out the door, lots of great restaurants nearby."
Lisa 2-night trip
Posted 4 days ago
Precise Tale Poggio Alla Sala
Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent
"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!"
Beren 2-night trip
Posted 10 days ago
Villa di Piazzano - Small Luxury Hotel of the World

Frequently asked questions

What are the best 5-star hotels in Castiglion Fiorentino?
Offering first-rate amenities and guest services, Expedia customers rate Relais Il Falconiere as one of the best 5-star hotels in Castiglion Fiorentino. You'll be in the lap of luxury from the minute you step foot into the lobby.
How much does it cost to stay in a 5-star hotel in Castiglion Fiorentino?
The amount you pay for a 5-star hotel in Castiglion Fiorentino can vary depending on when you want to travel and how long you plan to stay, among a number of factors. Use our price per night filter and other search tools to score the best deal on a luxurious getaway.
  • Search for the lowest price per night from ￥13,800
What makes a hotel 5 stars in Castiglion Fiorentino?
Exceptional guest service is integral to every 5-star hotel in Castiglion Fiorentino. From the second you arrive, staff are at your beck and call, whether recommending activities or providing in-room massages. Also, hotels have to offer upscale conveniences to obtain a 5-star rating. These can include luxury baths, a wellness center, swimming pools, gastronomic kitchens and knowledgeable concierge.

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