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

Luxury Hotels in Castiglion Fiorentino, Tuscany

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Check availability on Castiglion Fiorentino Luxury Hotels

Tonight
Oct 7 - Oct 8
Tomorrow
Oct 8 - Oct 9
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Castiglion Fiorentino luxury hotels

An outdoor event with people seated at tables, surrounded by stone buildings and greenery.
A couple in a bathtub with candles, suggesting a romantic setting.
A stone building with a grassy courtyard, a staircase, and a small garden area.
A modern interior with a stone wall, a wooden bench, and a glass door leading to a dark room.

1. San Michele al Castello

San Michele al Castello
Castiglion Fiorentino
P7,141
P8,138 total
includes taxes & fees
Oct 19 - Oct 20
San Michele al Castello
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.

2. Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux
Cortona
  • Tuscan elegance in a 5-star retreat with winery, Michelin-starred dining, and spa sanctuary.
P24,198
P26,900 total
includes taxes & fees
Nov 2 - Nov 3
Il Falconiere - Relais e Chateaux
A terrace with sun loungers, stone walls, and potted plants.
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.
A pool area with lounge chairs, a hot tub, and a view of mountains.

3. Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa
Cortona Old Town
  • Indulgent spa treatments and tuscan views define this luxury retreat in Cortona's heart.
P16,915
P19,172 total
includes taxes & fees
Oct 25 - Oct 26
Monastero di Cortona Hotel & Spa
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a stone building in the background.
A large estate with a swimming pool, surrounded by lush greenery and hills.
A buffet with various food items, a vase of flowers, and a mirror reflecting the room.
A hallway with a checkered floor, arched windows, and a chandelier.

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

Villa di Piazzano - Small Luxury Hotel of the World
Cortona
  • Historic Tuscan luxury with a poolside bar, boutique elegance, and stunning garden views.
P39,877
P44,430 total
includes taxes & fees
Oct 15 - Oct 16
Villa di Piazzano - Small Luxury Hotel of the World
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 modern bathroom with a large freestanding bathtub, a glass shower enclosure, and ornate mirrors.
A large pool with a curved edge, surrounded by a courtyard with a building featuring arched windows and columns.

5. Relais La Corte dei Papi

Relais La Corte dei Papi
Cortona
  • Tuscan retreat with full-service spa offers poolside dining, luxurious pampering, and champagne service in a rural setting.
P22,415
P24,939 total
includes taxes & fees
Nov 4 - Nov 5
Relais La Corte dei Papi
A restaurant with glass walls, tables set with white tablecloths, and chairs.
A greenhouse-style dining area with tables and chairs, surrounded by greenery and string lights.
A building with arched windows and a well-maintained garden with trimmed bushes and a large flower pot.
A long dining table set with plates, glasses, and floral centerpieces, surrounded by chairs.

6. La Cantina Relais - Fattoria Il Cipresso

La Cantina Relais - Fattoria Il Cipresso
Arezzo
P6,355
P7,414 total
includes taxes & fees
Oct 12 - Oct 13
La Cantina Relais - Fattoria Il Cipresso
An outdoor seating area with a pergola, a fire pit, and a flower arrangement.
A building with a symmetrical facade, multiple windows with shutters, and a gravel pathway leading to the entrance.
An aerial view of a rectangular swimming pool with multiple white umbrellas and lounge chairs around it.
A cozy living room with a brick ceiling, a white sofa, a coffee table, and a leather armchair.

7. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
P17,717
P19,770 total
includes taxes & fees
Oct 10 - Oct 11
Fontelunga Hotel & Villas
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 spacious interior with a high arched ceiling, large windows, and a central seating area with chairs and tables.
A large estate with multiple buildings, a swimming pool, and expansive green fields.

8. Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala
Montepulciano
  • Tuscan spa escape delivers rural tranquility and luxurious wellness at this Montepulciano retreat.
P34,941
P38,859 total
includes taxes & fees
Oct 11 - Oct 12
Precise Tale Poggio Alla Sala
A swimming pool with lounge chairs and a person in a patterned dress.
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.
A stone staircase with candles and a sign reading "CANTINA".

9. Castel Monastero - The Leading Hotels of the World

Castel Monastero - The Leading Hotels of the World
Castelnuovo Berardenga
  • Tuscan countryside retreat offers five-star luxury with full-service spa and two pools.
P35,618
P39,886 total
includes taxes & fees
Nov 4 - Nov 5
Castel Monastero - The Leading Hotels of the World
A spacious living room with a leather sofa, a wooden coffee table, and a view through large arched windows.
A dining table with two wine glasses, a vase with flowers, and a cheese board.
A large building with a pool, surrounded by greenery and trees.
A living room with a fireplace, a sofa, a coffee table, and a view of a bedroom through an arched doorway.

10. Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze
Montepulciano
P13,530
P15,166 total
includes taxes & fees
Nov 5 - Nov 6
Relais Villa Grazianella - UNA Esperienze
View all properties

Top Castiglion Fiorentino Hotel Reviews

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent
"Stunning property; a real representation of Tuscany with the long driveway of tall trees; staff was amazing; food was excellent; gardens, picturesque! We would highly recommend! Overall amazing !!!"
lynda 3-night trip
Posted 2 days ago
Villa di Piazzano - Small Luxury Hotel of the World
Hotel Corsignano

Hotel Corsignano

10/10 Excellent
"Everything was perfect the staff the hotel."
steve 1-night trip
Posted 13 days ago
Hotel Corsignano
Hotel Panoramic Montepulciano

Hotel Panoramic Montepulciano

10/10 Excellent
"buenas vistas panorámicas , es un hotel demasiado tranquilo , pero es muy bonito"
Enzo 2-night trip
Posted 3 weeks ago
Hotel Panoramic Montepulciano

Frequently asked questions

Are you looking for a luxury hotel for your Castiglion Fiorentino vacation?
Castiglion Fiorentino has some interesting things to see and do including Val di Chiana and Tennis Club Castiglionese, so you might want to take in the local sights during your visit.
What's the best luxury accommodation in Castiglion Fiorentino?
San Michele al Castello is a luxury B&B with a full-service spa and a rooftop terrace, and it's a popular choice for Expedia travelers looking for an elegant place to stay. Another upscale choice for your vacation is Villa Senaia.
When can I expect good weather in Castiglion Fiorentino?
Planning for the weather is an important factor for making your trip to Castiglion Fiorentino a success, especially when you're splurging. The hottest months are usually August and July with an average temp of 71°F, while the coldest months are January and February with an average of 42°F. Average annual precipitation for Castiglion Fiorentino is 35 inches.
What's there to see and do in Castiglion Fiorentino?
Enjoy Castiglion Fiorentino and visit Val di Chiana, Tennis Club Castiglionese, and Vasari Loggia. If you have a bit of extra time while you're in the area, you might want to check out Archaeological Museum and Cassero Tower.
How can I get around Castiglion Fiorentino?
It's easier to get around town comfortably when you know your options. If you want to explore the larger area, hop on a train at Castiglion Fiorentino Station.

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