Hotels in Castiglion Fiorentino

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Where to stay in Castiglion Fiorentino?

A neatly made bed with a quilted white cover, a grey headboard, and two pillows.

A modern interior with a stone wall, a wooden bench, and a glass door leading to a dark room.

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

An outdoor event with people seated at tables, surrounded by stone buildings and greenery.

1. San Michele al Castello

Castiglion Fiorentino

$114

$130 total

includes taxes & fees

Oct 19 - Oct 20

A modern hotel lobby with a reception desk, seating area, and a large plant.

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.

A hotel with a rooftop pool, a modern building with a sloped roof, and a view of the surrounding town.

2. Hotel Park

Castiglion Fiorentino

$106

$121 total

includes taxes & fees

Oct 20 - Oct 21

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

Castiglion Fiorentino

$87

$123 total

includes taxes & fees

Oct 8 - Oct 9

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 bedroom with a bed, a bedside table with a lamp, a dresser, and a mirror.

4. San Michele al Borgo

Castiglion Fiorentino

$141

$159 total

includes taxes & fees

Oct 19 - Oct 20

A tranquil sunset over a calm body of water with a gazebo structure in the foreground.

A cozy bedroom with a large bed, two armchairs, a small table with a teapot, and a window with a view of trees.

A large building with a tiled roof, surrounded by grapevines and a hay bale in a field.

An aerial view of a rural property with multiple buildings, a swimming pool, and surrounding agricultural fields.

5. Cortona Resort - Le Terre Dei Cavalieri

Cortona

$150

$170 total

includes taxes & fees

Oct 8 - Oct 9

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

Arezzo

$95

$112 total

includes taxes & fees

Oct 14 - Oct 15

A rustic outdoor dining area with stone walls, a table, and wicker chairs.

A bedroom with a large bed, wooden ceiling beams, a window with a view of greenery, and a small table with a bowl.

A stone building with a large arched doorway, surrounded by greenery and a hillside in the background.

A swimming pool with lounge chairs and umbrellas, surrounded by a brick pathway and greenery.

7. Relais Villa Baldelli

Cortona

$117

$138 total

includes taxes & fees

Oct 8 - Oct 9

A stone building with outdoor seating and a fountain.

A stone building with a tiled roof, a small window, and a metal fence.

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.

A stone building with multiple windows and a courtyard.

8. Villa Borgo San Pietro

Cortona

$125

$147 total

includes taxes & fees

Oct 15 - Oct 16

A person in a white robe standing by a window with a view of mountains.

A bedside table with a vase of flowers, a book, and a drawer.

A couple dining at a table with a scenic view of mountains and a lake.

A poolside area with lounge chairs and umbrellas, overlooking a scenic landscape.

9. Locanda agli Amici

Cortona

$97

$116 total

includes taxes & fees

Oct 13 - Oct 14

A view of a historic building with a green dome through a window, with candles and rolled towels on the windowsill.

A historic stone building with a sign reading "Hotel Italia."

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.

A lobby with a reception desk, a fireplace, and a large arched doorway leading outside.

10. Hotel Italia

Cortona Old Town

$113

$127 total

includes taxes & fees

Nov 4 - Nov 5

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 bedroom with a wooden headboard, two beds with pink and white bedding, a bedside table with a lamp, a small table with a bottle and glasses, and a window with a view of buildings.

11. B&B San Francesco

Cortona Old Town

$81

$111 total

includes taxes & fees

Oct 18 - Oct 19

A couple in a hot tub with a cityscape view through large windows.

A room with a large window, a vase of red flowers, and a white umbrella outside.

A hotel entrance with an arched doorway, a sign with the name 'Albergo I Michele', and a potted plant to the right.

A balcony with terracotta pots of flowers, a view of a rural landscape, and a stone building with a tiled roof.

12. Hotel San Michele

Cortona Old Town

$135

$157 total

includes taxes & fees

Oct 8 - Oct 9

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.

An outdoor dining area with tables and chairs, a garden with a lawn and potted plants, and a building with multiple windows and balconies.

A table set for a tea service with a tiered tray of pastries, a teapot, and various cups and saucers.

13. Hotel Villa Marsili

Cortona Old Town

$218

$249 total

includes taxes & fees

Oct 10 - Oct 11

A dining area with a table and chairs, large windows with curtains, and a view of a landscape.

A balcony with two lounge chairs, a small table with a drink, and a scenic view.

A hotel room with a large bed, a bedside table with a lamp, a mirror, and a framed picture on the wall.

A reception area with a wooden console table, two wall clocks, and a staircase leading to an upper level.

14. Hotel San Luca

Cortona Old Town

$81

$98 total

includes taxes & fees

Oct 28 - Oct 29

A stone building with a rustic charm, featuring a welcoming entrance and a small outdoor seating area.

A restaurant with a long communal table, wooden chairs, stone walls, and various kitchen utensils displayed on the walls.

A swimming pool with a stone wall and potted plants, surrounded by greenery and a clear sky.

A bedroom with a bed, a table with lemons, a window with curtains, and a radiator.

15. Locanda del Molino

Cortona

$77

$93 total

includes taxes & fees

Oct 27 - Oct 28

A gazebo with a glass enclosure, surrounded by potted plants and wicker furniture, overlooking a scenic landscape.

A spacious, well-lit restaurant with large windows, wooden tables, and potted plants.

A stone building with a red awning, potted plants, and a staircase leading to the entrance.

A person standing at the entrance of a building with a stone staircase leading up to a door.

16. Il Falconiere - Relais e Chateaux

Cortona

$385

$429 total

includes taxes & fees

Nov 2 - Nov 3

A building with multiple floors, a staircase leading to the entrance, and a small garden area with a palm tree and bushes.

A spacious room with a fireplace, multiple seating areas, and large windows allowing natural light.

A multi-story building with a rooftop terrace featuring outdoor seating and umbrellas.

A balcony with potted plants and a view of the sea.

17. Villa Santa Margherita

Cortona Old Town

$108

$141 total

includes taxes & fees

Oct 31 - Nov 1

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.

18. Monastero di Cortona Hotel & Spa

Cortona Old Town

$247

$281 total

includes taxes & fees

Oct 25 - Oct 26

A stone building with multiple windows and a central entrance.

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.

A terrace with a sofa and cushions, overlooking a cityscape and mountains.

19. Fondaco del Moro

Civitella in Val di Chiana

$69

$76 total

includes taxes & fees

Oct 9 - Oct 10

20. Agriturismo Parco Fiorito

Tuoro sul Trasimeno

$111

$169 total

includes taxes & fees

Oct 22 - Oct 23

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Go beyond your typical stay in Castiglion Fiorentino

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Apart hotel

Villa

Pool

Spa

Hot tub

Family friendly

Farm

Our prices for hotels in Castiglion Fiorentino are cheapest in September

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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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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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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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.

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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

Monastero di Cortona Hotel & Spa

10/10 Excellent

"Beautiful experience. Would recommend again and again."

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 !!!"

Relais Villa Grazianella - UNA Esperienze

10/10 Excellent

"I highly recommend this place Nice place with high trained staff Very clean rooms"

Nuovo Etruria Resort

10/10 Excellent

"Beautiful pool with view. Friendly staff members. Town is walkable but there is also a bus stop nearby that does the uphill drive to the top of town. Maybe not the most suitable for those who have proper mobility concerns for getting into town, but for everyone else the location is great"

Casanova - Panoramic Rooms and Suites

8/10 Good

"Great location and lovely pool. Rooms were large but the place is definitely dated. Breakfast was decent with a lot of options. Parking wasn’t all that great but nevertheless on the property itself"

Relais Cloister Pienza

10/10 Excellent

"Just a fantastic place in the most beautiful setting. Medieval historical ambiance with a modern vibe. Pool area - perfect. Breakfast - perfect. Dinner - perfect. Views - incredible! Location - the best in town!"

Palazzo Brandano

10/10 Excellent

"Bello lugar, bella vista panoramica. Hay que trasladarse para comer a pueblos vecinos próximos."

Hotel Villa Ricci

10/10 Excellent

"Personal, muy amable y educado, muy cálida, recepción, lindo hotel. Lo aconsejo para quienes quieran visitar la toscana y sobretodo Montepulciano."

Hotel Corsignano

10/10 Excellent

"Everything was perfect the staff the hotel."

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 25 apartments or 89 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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Book Hotels in Castiglion Fiorentino on it.hotels.com

Hotels in Castiglion Fiorentino

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Where to stay in Castiglion Fiorentino?

1. San Michele al Castello

2. Hotel Park

3. Bed & Breakfast Viziottavo

4. San Michele al Borgo

5. Cortona Resort - Le Terre Dei Cavalieri

6. La Cantina Relais - Fattoria Il Cipresso

7. Relais Villa Baldelli

8. Villa Borgo San Pietro

9. Locanda agli Amici

10. Hotel Italia

11. B&B San Francesco

12. Hotel San Michele

13. Hotel Villa Marsili

14. Hotel San Luca

15. Locanda del Molino

16. Il Falconiere - Relais e Chateaux

17. Villa Santa Margherita

18. Monastero di Cortona Hotel & Spa

19. Fondaco del Moro

20. Agriturismo Parco Fiorito

Go beyond your typical stay in Castiglion Fiorentino

Price trends for hotels in Castiglion Fiorentino

Typical weather for Castiglion Fiorentino

Top landmarks in Castiglion Fiorentino

Tennis Club Castiglionese

Vasari Loggia

Cassero Tower

Archaeological Museum

Agricola Buccelletti Winery

Learn more about Castiglion Fiorentino

Check out reviews of Castiglion Fiorentino hotels guests love

Monastero di Cortona Hotel & Spa

Villa di Piazzano - Small Luxury Hotel of the World

Relais Villa Grazianella - UNA Esperienze

Nuovo Etruria Resort

Casanova - Panoramic Rooms and Suites

Relais Cloister Pienza

Palazzo Brandano

Hotel Villa Ricci

Hotel Corsignano

Frequently asked questions

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