Hotels in Castiglion Fiorentino

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Tonight
Sep 27 - Sep 28
Tomorrow
Sep 28 - Sep 29
Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11

Where to stay in Castiglion Fiorentino?

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 cozy room with a bed, candles, a bottle of wine, and fresh fruits.

1. San Michele al Castello

San Michele al Castello
Castiglion Fiorentino
$115
$131 total
includes taxes & fees
Sep 30 - Oct 1
San Michele al Castello
A modern hotel lobby with a reception desk, seating area, and a large plant.
A modern library with leather sofas, bookshelves, and a large window.
A modern bar area with a counter, bar stools, and a seating area with chairs.
A hotel with a modern design, featuring a prominent green sign, multiple balconies, and well-maintained landscaping.

2. Hotel Park

Hotel Park
Castiglion Fiorentino
$107
$122 total
includes taxes & fees
Oct 1 - Oct 2
Hotel Park
A breakfast buffet with various food items and beverages.
A multi-story building with green shutters, a balcony, and a sign with a musical note.
A breakfast setting with a waffle, a glass pitcher of orange juice, and a tray of pastries.
A bedroom with a dark-colored bed, wooden ceiling beams, a white bedside table, and a wall-mounted light fixture.

3. Bed & Breakfast Viziottavo

Bed & Breakfast Viziottavo
Castiglion Fiorentino
$88
$124 total
includes taxes & fees
Oct 8 - Oct 9
Bed & Breakfast Viziottavo
A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.
A breakfast setting with a fireplace, a table with plates, glasses, and a croissant.
A couple in a hot tub with a bottle of champagne and a flower vase.
A bedroom with a bed, a bedside table with a lamp, a dresser, and a mirror.

4. San Michele al Borgo

San Michele al Borgo
Castiglion Fiorentino
$143
$162 total
includes taxes & fees
Sep 29 - Sep 30
San Michele al Borgo
A stone building with a courtyard, outdoor seating, and a view of the landscape.
A garden with a stone pathway, a wooden barrel, and a view of the countryside.
A wine cellar with wooden barrels, shelves of wine bottles, and a brick archway.
A stone building with a pool and outdoor seating area, surrounded by trees and a view of the countryside.

5. Villa Schiatti

Villa Schiatti
Castiglion Fiorentino
$158
$178 total
includes taxes & fees
Sep 28 - Sep 29
Villa Schiatti
A restaurant with glass walls, tables set with white tablecloths, and chairs.
A building with arched windows and a well-maintained garden with trimmed bushes and a large flower pot.
A skylight with a view of a tree and a distant building.
A greenhouse-style dining area with tables and chairs, surrounded by greenery and string lights.

6. La Cantina Relais - Fattoria Il Cipresso

La Cantina Relais - Fattoria Il Cipresso
Arezzo
$101
$117 total
includes taxes & fees
Oct 12 - Oct 13
La Cantina Relais - Fattoria Il Cipresso
A large, two-story building with a symmetrical facade, a central entrance, and evenly spaced windows.
A restaurant interior with tables set for dining, a kitchen area, and a wine display.
A hotel lobby with a brick archway, a reception desk, and potted plants.
A nighttime swimming pool with a clear reflection, surrounded by trees and lounge chairs.

7. Hotel Le Capanne

Hotel Le Capanne
Arezzo
$117
$135 total
includes taxes & fees
Oct 12 - Oct 13
Hotel Le Capanne
A stone building with outdoor seating and a fountain.
A stone building with multiple windows and a courtyard.
A bedroom with a bed, a dining table, and a TV. There is a balcony with a view of greenery.
A rectangular swimming pool with clear blue water, surrounded by white lounge chairs and umbrellas, set against a backdrop of trees and a clear sky.

8. Villa Borgo San Pietro

Villa Borgo San Pietro
Cortona
$117
$137 total
includes taxes & fees
Oct 5 - Oct 6
Villa Borgo San Pietro
A tranquil sunset over a calm body of water with a gazebo structure in the foreground.
A building with a rustic facade, a door with shutters, and a small outdoor seating area under a vine-covered archway.
A large building with a tiled roof, surrounded by grapevines and a hay bale in a field.
A cozy bedroom with a large bed, two armchairs, a small table with a teapot, and a window with a view of trees.

9. Cortona Resort - Le Terre Dei Cavalieri

Cortona Resort - Le Terre Dei Cavalieri
Cortona
$132
$151 total
includes taxes & fees
Sep 28 - Sep 29
Cortona Resort - Le Terre Dei Cavalieri
A rustic outdoor dining area with stone walls, a table, and wicker chairs.
A stone pathway leading through an arched stone structure, surrounded by greenery and a lamp post.
A bedroom with a large bed, wooden ceiling beams, a window with a view of greenery, and a small table with a bowl.
A swimming pool with lounge chairs and umbrellas, surrounded by a brick pathway and greenery.

10. Relais Villa Baldelli

Relais Villa Baldelli
Cortona
$128
$150 total
includes taxes & fees
Sep 28 - Sep 29
Relais Villa Baldelli
A modern interior with a decorative wall, a bed with pillows, and a small table with a lamp.
A modern hotel lobby with a large mirror, potted plants, and a spacious seating area.
A rooftop terrace with outdoor seating, a pergola, and a view of hills.
A spa area with a circular hot tub surrounded by mosaic tiles, a stone bench, and a small table with a bowl and a candle.

11. Il Gentiluomo Hotel & SPA

Il Gentiluomo Hotel & SPA
Arezzo
$74
$88 total
includes taxes & fees
Oct 1 - Oct 2
Il Gentiluomo Hotel & SPA
A dining area with a table and chairs, large windows with curtains, and a view of a landscape.
A hotel room with a large bed, a bedside table with a lamp, a mirror, and a framed picture on the wall.
A balcony with two lounge chairs, a small table with a drink, and a scenic view.
A window view of a town with buildings, trees, and parked cars.

12. Hotel San Luca

Hotel San Luca
Cortona Old Town
$79
$96 total
includes taxes & fees
Oct 21 - Oct 22
Hotel San Luca
A gazebo with a glass enclosure, surrounded by potted plants and wicker furniture, overlooking a scenic landscape.
A person standing at the entrance of a building with a stone staircase leading up to a door.
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.

13. Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux
Cortona
$424
$475 total
includes taxes & fees
Oct 27 - Oct 28
Il Falconiere - Relais e Chateaux
A view of a historic building with a green dome through a window, with candles and rolled towels on the windowsill.
A restaurant with outdoor seating overlooking a historic town and the sea.
A lobby with a reception desk, a fireplace, and a large arched doorway leading outside.
A bedroom with a stone wall, a bed with a headboard, a desk with a computer, a chair, a window with a view, and a ceiling with exposed beams.

14. Hotel Italia

Hotel Italia
Cortona Old Town
$132
$151 total
includes taxes & fees
Oct 27 - Oct 28
Hotel Italia
A stone building with multiple windows and a central entrance.
A terrace with a sofa and cushions, overlooking a cityscape and mountains.
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.

15. Fondaco del Moro

Fondaco del Moro
Civitella in Val di Chiana
$70
$77 total
includes taxes & fees
Sep 29 - Sep 30
Fondaco del Moro
A building with a stone pathway leading to an arched entrance, flanked by potted plants and lit by ground lights.
A spacious living room with a yellow sofa, a wooden coffee table, and a floral rug. There are two armchairs and a dining table with chairs. The room has a large window with curtains, a mirror, and wall-mounted lights.
A hotel room with a fireplace, two armchairs, a bed, and a dresser.
A table set for a tea service with a tiered tray of pastries, a teapot, and various cups and saucers.

16. Hotel Villa Marsili

Hotel Villa Marsili
Cortona Old Town
$201
$231 total
includes taxes & fees
Oct 10 - Oct 11
Hotel Villa Marsili
A terrace with sun loungers, stone walls, and potted plants.
A narrow hallway with a stone wall and a clock.
A spacious lobby with a high ceiling, a grand chandelier, and a staircase leading to an upper level.
A historic town with traditional architecture, a central courtyard with a swimming pool, and a view of distant mountains.

17. Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa
Cortona Old Town
$251
$285 total
includes taxes & fees
Oct 25 - Oct 26
Monastero di Cortona Hotel & Spa
A person in a white robe standing by a window with a view of mountains.
A poolside area with lounge chairs and umbrellas, overlooking a scenic landscape.
A bedside table with a vase of flowers, a book, and a drawer.
A person seated at a table with a glass of white wine, in a room with tables and chairs, and a plant in the background.

18. Locanda agli Amici

Locanda agli Amici
Cortona
$100
$119 total
includes taxes & fees
Oct 25 - Oct 26
Locanda agli Amici
A courtyard with stone buildings, a gravel path, and potted plants.
A view through a window of a courtyard with a stone building, a clock tower, and a garden with a geometric flower bed.
A wooden staircase with a handrail on both sides, leading to an upper floor.
A cobblestone street with terracotta planters and a sign indicating the location of the Chiesa di San Francesco.

19. B&B San Francesco

B&B San Francesco
Cortona Old Town
$82
$112 total
includes taxes & fees
Sep 28 - Sep 29
B&B San Francesco
A building with multiple floors, a staircase leading to the entrance, and a small garden area with a palm tree and bushes.
A multi-story building with a rooftop terrace featuring outdoor seating and umbrellas.
A spacious room with a fireplace, multiple seating areas, and large windows allowing natural light.
A buffet table with various food items, including cookies, pastries, and dairy products, with labels indicating gluten-free options.

20. Villa Santa Margherita

Villa Santa Margherita
Cortona Old Town
$117
$134 total
includes taxes & fees
Sep 28 - Sep 29
Villa Santa Margherita
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A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.
A breakfast setting with a fireplace, a table with plates, glasses, and a croissant.
A couple in a hot tub with a bottle of champagne and a flower vase.
A bedroom with a bed, a bedside table with a lamp, a dresser, and a mirror.

San Michele al Borgo

San Michele al Borgo
Castiglion Fiorentino
$136
per night
$308 total
includes taxes & fees
San Michele al Borgo

Agriturismo Borgo Santa Lucia, Villa Mimosa

Agriturismo Borgo Santa Lucia, Villa Mimosa
Castiglion Fiorentino
$251
per night
$733 total
includes taxes & fees
Sign in for extra savings
Agriturismo Borgo Santa Lucia, Villa Mimosa
A swimming pool with a stone border, surrounded by a grassy area with lounge chairs and umbrellas.
A rustic building with a brick facade, a stone wall, and a small arched entrance.
A bedroom with a wooden ceiling, a large bed with a patterned bedspread, a chandelier, a bedside table with a lamp, a mirror, and a standing fan.
A patio with two brick arches, a table, and chairs. There are flower boxes with plants and flowers on the arches.

Villa Cecilia

Villa Cecilia
Castiglion Fiorentino
Villa Cecilia
An outdoor dining table set with plates, glasses, and cutlery, surrounded by chairs and plants.
A stone building with red shutters and a central door, surrounded by potted plants.
A bedroom with a wooden bed, two bedside lamps, a nightstand, a chair, a window with curtains, and a door.
A bathroom with a pedestal sink, a toilet, a bidet, and a shower enclosure.

Galleria DI Brolio

Galleria DI Brolio
Castiglion Fiorentino
Galleria DI Brolio
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and trees.
A two-story building with a garden in front.
A bedroom with a wooden headboard, two bedside tables with lamps, a bed with a patterned bedspread, a radiator, and a window with blinds.
A dining area with a table set for two, featuring wine bottles, glasses, and a candle.

Villa Degli Olivi

Villa Degli Olivi
Castiglion Fiorentino
Villa Degli Olivi

Check out pet-friendly hotels in Castiglion Fiorentino

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 cozy room with a bed, candles, a bottle of wine, and fresh fruits.

San Michele al Castello

San Michele al Castello
Castiglion Fiorentino
$115
$131 total
includes taxes & fees
Sep 30 - Oct 1
San Michele al Castello
A breakfast buffet with various food items and beverages.
A multi-story building with green shutters, a balcony, and a sign with a musical note.
A breakfast setting with a waffle, a glass pitcher of orange juice, and a tray of pastries.
A bedroom with a dark-colored bed, wooden ceiling beams, a white bedside table, and a wall-mounted light fixture.

Bed & Breakfast Viziottavo

Bed & Breakfast Viziottavo
Castiglion Fiorentino
$88
$124 total
includes taxes & fees
Oct 8 - Oct 9
Bed & Breakfast Viziottavo
A modern hotel lobby with a reception desk, seating area, and a large plant.
A modern library with leather sofas, bookshelves, and a large window.
A modern bar area with a counter, bar stools, and a seating area with chairs.
A hotel with a modern design, featuring a prominent green sign, multiple balconies, and well-maintained landscaping.

Hotel Park

Hotel Park
Castiglion Fiorentino
$107
$122 total
includes taxes & fees
Oct 1 - Oct 2
Hotel Park
A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.
A breakfast setting with a fireplace, a table with plates, glasses, and a croissant.
A couple in a hot tub with a bottle of champagne and a flower vase.
A bedroom with a bed, a bedside table with a lamp, a dresser, and a mirror.

San Michele al Borgo

San Michele al Borgo
Castiglion Fiorentino
$143
$162 total
includes taxes & fees
Sep 29 - Sep 30
San Michele al Borgo
A stone building with a courtyard, outdoor seating, and a view of the landscape.
A garden with a stone pathway, a wooden barrel, and a view of the countryside.
A wine cellar with wooden barrels, shelves of wine bottles, and a brick archway.
A stone building with a pool and outdoor seating area, surrounded by trees and a view of the countryside.

Villa Schiatti

Villa Schiatti
Castiglion Fiorentino
$158
$178 total
includes taxes & fees
Sep 28 - Sep 29
Villa Schiatti
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.
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Our prices for hotels in Castiglion Fiorentino are cheapest in September
Price trends for hotels in Castiglion Fiorentino
Pricing is based on two traveler single night rates
View properties in September
Typical weather for Castiglion Fiorentino
September
High 24°C / low 14°C. Sunny most days.
View properties in September
24°
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19°
10°
13°
6°
9°
2°
7°
1°
9°
2°
13°
4°
17°
7°
21°
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26°
15°
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18°
Monthly weather averages (˚C)

Top landmarks in Castiglion Fiorentino

Tennis Club Castiglionese

Tennis Club Castiglionese is in the heart of Castiglion Fiorentino, so why not stop by during your stay.
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Cassero Tower

9.4/10 (6 reviews)
If you're planning a bit of sightseeing during your trip, head to Cassero Tower— just one of the monuments in central Castiglion Fiorentino.
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Vasari Loggia

10.0/10 (2 reviews)
If you're planning a bit of sightseeing during your trip, head to Vasari Loggia— just one of the monuments in central Castiglion Fiorentino.
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Archaeological Museum

9.6/10 (5 reviews)
If museums are on your list of things to see, then you might want to head to Archaeological Museum, located in the heart of Castiglion Fiorentino.If you want to experience more of the culture Castiglion Fiorentino has to offer, head to Tennis Club Castiglionese and Cassero Tower.
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Agricola Buccelletti Winery

10.0/10 (2 reviews)
Travelers might want a tour of Agricola Buccelletti Winery, just one of the places to visit in the heart of La Strada-Santa Cristina.
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Learn more about Castiglion Fiorentino

Castiglion Fiorentino is well-known for its attractions such as Val di Chiana and Tennis Club Castiglionese.

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

Check out reviews of Castiglion Fiorentino hotels guests love

Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

10/10 Excellent
"In addition to the property being absolutely beautiful, the"
Michele 3-night trip
Posted 6 hours ago
Relais Villa Grazianella - UNA Esperienze
Villa Tiberini Wine Relais

Villa Tiberini Wine Relais

10/10 Excellent
"This place was spectacular. Luca and Nunzia became like family. Their staff was always helpful. The property is gorgeous!!! We also did the wine tasting lunch and that was one of pur favorite activities of a 5 week trip."
Kristine 7-night trip
Posted 8 hours ago
Villa Tiberini Wine Relais
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 1 day ago
Precise Tale Poggio Alla Sala
Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites

10/10 Excellent
"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 again. A short walk into San Quirico d'Orcia with several good restaurants and a COOP store for drinks and groceries."
Zoltan 5-night trip
Posted 2 days ago
Casanova - Panoramic Rooms and Suites
Hotel Corsignano

Hotel Corsignano

10/10 Excellent
"Everything was perfect the staff the hotel."
steve 1-night trip
Posted 2 days ago
Hotel Corsignano
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Service was top notch and Claudio at the bar made the best cocktails"
Alexander 2-night trip
Posted 5 days ago
Monastero di Cortona Hotel & Spa
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 6 days ago
Villa di Piazzano - Small Luxury Hotel of the World
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 7 days ago
Hotel Panoramic Montepulciano
Hotel San Gregorio

Hotel San Gregorio

8/10 Good
"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 using the shower handle. Pool area is restful. Enjoyed our stay"
JANET 3-night trip
Posted 9 days ago
Hotel San Gregorio

Frequently asked questions

What accommodations do travelers recommend in Castiglion Fiorentino?
Guests like Villa di Piazzano - Small Luxury Hotel of the World, Hotel Continentale and Monastero di Cortona Hotel & Spa.
Where can I find free parking with my stay in Castiglion Fiorentino?
These hotels offer the perk of free parking: San Michele al Castello, Bed & Breakfast Viziottavo and Villa Senaia.
Can I book a refundable accommodation in Castiglion Fiorentino?
If you want the flexibility to change your travel plans to Castiglion Fiorentino, most accommodations offer refundable* rates you can book. You can see these properties by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Castiglion Fiorentino if I want a vacation home instead of a hotel?
If you want to find a good alternative to a hotel, look over our selection of 85 vacation homes. You can also book one of 26 apartments or 88 villas.
What will the weather in Castiglion Fiorentino be like during my vacation?
August and July are typically the warmest months in Castiglion Fiorentino when the average temp is 71°F. January and February are the coldest months when the average temperature is 42°F. November and October are the months with the most rain.
Why should I book my Castiglion Fiorentino hotel with Hotels.com?
There are lots of reasons to book your Castiglion Fiorentino trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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