Hotels in Castiglion Fiorentino

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Check prices for these dates

Tonight
Oct 16 - Oct 17
Tomorrow
Oct 17 - Oct 18
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Where to stay in Castiglion Fiorentino?

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 hotel with a rooftop pool, a modern building with a sloped roof, and a view of the surrounding town.
A modern bar area with a counter, bar stools, and a seating area with chairs.

1. Hotel Park

Hotel Park
Castiglion Fiorentino
$105
$120 total
includes taxes & fees
Oct 27 - Oct 28
Hotel Park
An outdoor gathering with people around tables, a grassy area, and buildings in the background.
A cozy room with a bed, candles, a bottle of wine, and fresh fruits.
A modern interior with a stone wall, a wooden bench, and a glass door leading to a dark room.
A couple in a bathtub with candles, suggesting a romantic setting.

2. San Michele al Castello

San Michele al Castello
Castiglion Fiorentino
$113
$129 total
includes taxes & fees
Oct 28 - Oct 29
San Michele al Castello
A breakfast buffet with various food items and beverages.
A breakfast setting with a waffle, a glass pitcher of orange juice, and a tray of pastries.
A staircase with a wooden handrail and metal balusters, decorated with a floral arrangement at the bottom.
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
$87
$122 total
includes taxes & fees
Nov 13 - Nov 14
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 bedroom with a bed, a bedside table with a lamp, a dresser, and a mirror.
A spa area with a reception desk, a chair, and a wall with a logo.

4. San Michele al Borgo

San Michele al Borgo
Castiglion Fiorentino
$140
$159 total
includes taxes & fees
Oct 28 - Oct 29
San Michele al Borgo
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 swimming pool with lounge chairs and umbrellas, surrounded by a brick pathway and greenery.
A bedroom with a large bed, wooden ceiling beams, a window with a view of greenery, and a small table with a bowl.

5. Relais Villa Baldelli

Relais Villa Baldelli
Cortona
$117
$137 total
includes taxes & fees
Oct 17 - Oct 18
Relais Villa Baldelli
A tranquil sunset over a calm body of water with a gazebo structure in the foreground.
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.
An aerial view of a rural property with multiple buildings, a swimming pool, and surrounding agricultural fields.

6. Cortona Resort - Le Terre Dei Cavalieri

Cortona Resort - Le Terre Dei Cavalieri
Cortona
$195
$220 total
includes taxes & fees
Oct 17 - Oct 18
Cortona Resort - Le Terre Dei Cavalieri
A restaurant with glass walls, tables set with white tablecloths, and chairs.
A long dining table set with plates, glasses, and floral centerpieces, surrounded by chairs.
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.

7. La Cantina Relais - Fattoria Il Cipresso

La Cantina Relais - Fattoria Il Cipresso
Arezzo
$96
$113 total
includes taxes & fees
Oct 19 - Oct 20
La Cantina Relais - Fattoria Il Cipresso
A stone building with outdoor seating and a fountain.
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.
A stone building with a tiled roof, a small window, and a metal fence.

8. Villa Borgo San Pietro

Villa Borgo San Pietro
Cortona
$129
$151 total
includes taxes & fees
Oct 17 - Oct 18
Villa Borgo San Pietro
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 person seated at a table with a glass of white wine, in a room with tables and chairs, and a plant in the background.
A couple dining at a table with a scenic view of mountains and a lake.

9. Locanda agli Amici

Locanda agli Amici
Cortona
$98
$116 total
includes taxes & fees
Oct 18 - Oct 19
Locanda agli Amici
A large, two-story building with a symmetrical facade, a central entrance, and evenly spaced windows.
An outdoor dining area with tables set for breakfast, including pastries, fruit, and beverages.
A nighttime swimming pool with a clear reflection, surrounded by trees and lounge chairs.
A hotel lobby with a brick archway, a reception desk, and potted plants.

10. Hotel Le Capanne

Hotel Le Capanne
Arezzo
$105
$123 total
includes taxes & fees
Oct 25 - Oct 26
Hotel Le Capanne
A view of a historic building with a green dome through a window, with candles and rolled towels on the windowsill.
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.
A historic stone building with a sign reading "Hotel Italia."

11. Hotel Italia

Hotel Italia
Cortona Old Town
$111
$125 total
includes taxes & fees
Nov 4 - Nov 5
Hotel Italia
A couple in a hot tub with a cityscape view through large windows.
A balcony with terracotta pots of flowers, a view of a rural landscape, and a stone building with a tiled roof.
A hotel entrance with an arched doorway, a sign with the name 'Albergo I Michele', and a potted plant to the right.
A room with a large window, a vase of red flowers, and a white umbrella outside.

12. Hotel San Michele

Hotel San Michele
Cortona Old Town
$120
$136 total
includes taxes & fees
Nov 5 - Nov 6
Hotel San Michele
A courtyard with stone buildings, a gravel path, and potted plants.
A cobblestone street with terracotta planters and a sign indicating the location of the Chiesa di San Francesco.
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.
A wooden staircase with a handrail on both sides, leading to an upper floor.

13. B&B San Francesco

B&B San Francesco
Cortona Old Town
$80
$107 total
includes taxes & fees
Nov 4 - Nov 5
B&B San Francesco
A stone building with a rustic charm, featuring a welcoming entrance and a small outdoor seating area.
A cozy living room with a fireplace, a sofa, a dining table, and various decorative items.
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.

14. Locanda del Molino

Locanda del Molino
Cortona
$76
$93 total
includes taxes & fees
Oct 28 - Oct 29
Locanda del Molino
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.

15. Villa Santa Margherita

Villa Santa Margherita
Cortona Old Town
$107
$140 total
includes taxes & fees
Oct 31 - Nov 1
Villa Santa Margherita
A building with a stone pathway leading to an arched entrance, flanked by potted plants and lit by ground lights.
A hotel room with a fireplace, two armchairs, a bed, and a dresser.
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 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.

16. Hotel Villa Marsili

Hotel Villa Marsili
Cortona Old Town
$231
$259 total
includes taxes & fees
Nov 2 - Nov 3
Hotel Villa Marsili
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 reception area with a wooden console table, two wall clocks, and a staircase leading to an upper level.
A balcony with two lounge chairs, a small table with a drink, and a scenic view.

17. Hotel San Luca

Hotel San Luca
Cortona Old Town
$79
$96 total
includes taxes & fees
Oct 26 - Oct 27
Hotel San Luca
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 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.

18. Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa
Cortona Old Town
$244
$277 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 person in a swimming pool with a view of trees and mountains through a window.
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.

19. Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux
Cortona
$367
$409 total
includes taxes & fees
Nov 15 - Nov 16
Il Falconiere - Relais e Chateaux
Restaurant
Room
Front of property
Reception

20. Agriturismo Parco Fiorito

Agriturismo Parco Fiorito
Tuoro sul Trasimeno
$111
$168 total
includes taxes & fees
Oct 22 - Oct 23
Agriturismo Parco Fiorito
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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 October
Typical weather for Castiglion Fiorentino
October
High 19°C / low 10°C. Sunny most days.
View properties in October
19°
10°
13°
6°
9°
2°
7°
1°
9°
2°
13°
4°
17°
7°
21°
10°
26°
15°
30°
18°
30°
18°
24°
14°
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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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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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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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

Hotel San Gregorio

Hotel San Gregorio

10/10 Excellent
"Get"
Taisa 1-night trip
Posted 10 hours ago
Hotel San Gregorio
Hotel Villa Ricci

Hotel Villa Ricci

8/10 Good
"Bien situe Bon déjeuner"
Marc 2-night trip
Posted 3 days ago
Hotel Villa Ricci
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Frederico went above and beyond to transfer us to our villa and Giulio was a fantastic bartender"
lise 1-night trip
Posted 3 days ago
Monastero di Cortona Hotel & Spa
Hotel Continentale

Hotel Continentale

10/10 Excellent
"The location of this hotel is excellent!"
Thanh 2-night trip
Posted 4 days ago
Hotel Continentale
Il Gentiluomo Hotel & SPA

Il Gentiluomo Hotel & SPA

10/10 Excellent
"It was perfect….the outside was a little run down but the inside was perfect. They had just moved and not cleaned up so that did not help the appearance."
terri 3-night trip
Posted 5 days ago
Il Gentiluomo Hotel & SPA
Palazzo Brandano

Palazzo Brandano

10/10 Excellent
"Large rooms, helpful staff, delicious breakfast at a very reasonable price. There’s no water by the hotel, as seen in the picture. It’s located on a very old walled town… quite quaint."
Peter 4-night trip
Posted 6 days ago
Palazzo Brandano
Hotel Panoramic Montepulciano

Hotel Panoramic Montepulciano

8/10 Good
"Ok."
Yuanjun 1-night trip
Posted 7 days ago
Hotel Panoramic Montepulciano
Casanova - Panoramic Rooms and Suites

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"
Sunil 4-night trip
Posted 13 days ago
Casanova - Panoramic Rooms and Suites
Relais Cloister Pienza

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!"
Karen 1-night trip
Posted 13 days ago
Relais Cloister Pienza

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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