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

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Check availability on Castiglion Fiorentino Luxury Hotels

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

Our top choices for Castiglion Fiorentino luxury hotels

An outdoor event with people seated at tables, surrounded by stone buildings and greenery.
A stone building with a grassy courtyard, a staircase, and a small garden area.
A couple in a bathtub with candles, suggesting a romantic setting.
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
S$162
includes taxes & fees
19 Oct - 20 Oct
San Michele al Castello
A restaurant with glass walls, tables set with white tablecloths, and chairs.
A skylight with a view of a tree and a distant building.
A building with arched windows and a well-maintained garden with trimmed bushes and a large flower pot.
A greenhouse-style dining area with tables and chairs, surrounded by greenery and string lights.

2. La Cantina Relais - Fattoria Il Cipresso

La Cantina Relais - Fattoria Il Cipresso
Arezzo
S$146
includes taxes & fees
12 Oct - 13 Oct
La Cantina Relais - Fattoria Il Cipresso
Pool
Outdoor spa tub
Exterior
Reception

3. iConic Wellness Resort

iConic Wellness Resort
Arezzo
S$113
includes taxes & fees
25 Oct - 26 Oct
iConic Wellness Resort
A terrace with sun loungers, stone walls, and potted plants.
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.
A narrow hallway with a stone wall and a clock.

4. 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.
S$390
includes taxes & fees
25 Oct - 26 Oct
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 spacious, well-lit restaurant with large windows, wooden tables, and potted plants.

5. 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.
S$547
includes taxes & fees
2 Nov - 3 Nov
Il Falconiere - Relais e Chateaux
A stone building with multiple windows and a central entrance.
A hotel room with a bed, a yellow armchair, a stone wall, and a window with a lamp.
A dining area with a table set for two, white chairs, and a stone-patterned floor.
A narrow stone pathway leading to a stone archway, surrounded by lush greenery and a stone wall.

6. Fondaco del Moro

Fondaco del Moro
Civitella in Val di Chiana
S$97
includes taxes & fees
11 Oct - 12 Oct
Fondaco del Moro
A large, rectangular swimming pool surrounded by a well-maintained lawn, with a house and garden in the background.
A traditional villa with a garden, outdoor seating, and a clear blue sky.
A sauna, a glass-enclosed shower, and a bathtub with a modern design.
A well-maintained lawn with a brick house and a flag, surrounded by trees and a clear sky.

7. Casa Bellavista

Casa Bellavista
Cortona
S$257
includes taxes & fees
18 Oct - 19 Oct
Casa Bellavista
An upper floor view of a courtyard with stone walls, arched doorways, and seating areas with potted plants.
A bedroom with a bed, two bedside tables, a nightstand, a door with a sign, and a wall-mounted light fixture.
A bar area with shelves of liquor bottles, a cash register, and a decorative plant.
A breakfast buffet with various food items and beverages.

8. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
S$203
includes taxes & fees
2 Nov - 3 Nov
B&B Piccolo Hotel
An outdoor seating area with a pergola, a fire pit, and a flower arrangement.
A cozy living room with a brick ceiling, a white sofa, a coffee table, and a leather armchair.
A long dining table set for a formal meal under an umbrella, with chairs on both sides and candles on the table.
An aerial view of a rectangular swimming pool with multiple white umbrellas and lounge chairs around it.

9. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
S$369
includes taxes & fees
11 Oct - 12 Oct
Fontelunga Hotel & Villas
A table set with a bottle of wine, two wine glasses, and a vase with flowers.
A living room with a sofa, armchair, and a wooden cabinet.
An open door leading to a balcony with a stone wall and a view of a landscaped garden.
A hotel room with a bed, a sofa, a chair, a small table with a lamp, and a window with a view of a green landscape.

10. Poggio Paradiso Resort & Spa

Poggio Paradiso Resort & Spa
Torrita di Siena
S$303
includes taxes & fees
3 Nov - 4 Nov
Poggio Paradiso Resort & Spa
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 3 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 panorรกmicas , 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 holiday?
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 option 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 travellers looking for an elegant place to stay. Another upscale option for your stay 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 temperature of 22ยฐC, while the coldest months are January and February, with an average of 6ยฐC. Average annual precipitation for Castiglion Fiorentino is 901 mm.
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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