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Hotels in Castiglion Fiorentino

October 2026
5
November 2026

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This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

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 modern design, featuring a prominent green sign, multiple balconies, and well-maintained landscaping.
A modern bar area with a counter, bar stools, and a seating area with chairs.

1. Hotel Park

Hotel Park
Castiglion Fiorentino
$106
$121 total
includes taxes & fees
Oct 7 - Oct 8
Hotel Park
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.

2. San Michele al Castello

San Michele al Castello
Castiglion Fiorentino
$114
$130 total
includes taxes & fees
Oct 6 - Oct 7
San Michele al Castello
A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.
A couple in a hot tub with a bottle of champagne and a flower vase.
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.

3. San Michele al Borgo

San Michele al Borgo
Castiglion Fiorentino
$141
$160 total
includes taxes & fees
Oct 6 - Oct 7
San Michele al Borgo
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 multi-story building with green shutters, a balcony, and a sign with a musical note.

4. Bed & Breakfast Viziottavo

Bed & Breakfast Viziottavo
Castiglion Fiorentino
$87
$123 total
includes taxes & fees
Oct 8 - Oct 9
Bed & Breakfast Viziottavo
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 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.

5. Cortona Resort - Le Terre Dei Cavalieri

Cortona Resort - Le Terre Dei Cavalieri
Cortona
$150
$171 total
includes taxes & fees
Oct 6 - Oct 7
Cortona Resort - Le Terre Dei Cavalieri
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 skylight with a view of a tree and a distant building.
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
$96
$112 total
includes taxes & fees
Oct 14 - Oct 15
La Cantina Relais - Fattoria Il Cipresso
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.

7. Villa Borgo San Pietro

Villa Borgo San Pietro
Cortona
$113
$133 total
includes taxes & fees
Oct 6 - Oct 7
Villa Borgo San Pietro
A rustic outdoor dining area with stone walls, a table, and wicker chairs.
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.
A bedroom with a large bed, wooden ceiling beams, a window with a view of greenery, and a small table with a bowl.

8. Relais Villa Baldelli

Relais Villa Baldelli
Cortona
$127
$148 total
includes taxes & fees
Oct 7 - Oct 8
Relais Villa Baldelli
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.

9. B&B San Francesco

B&B San Francesco
Cortona Old Town
$81
$111 total
includes taxes & fees
Oct 6 - Oct 7
B&B San Francesco
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 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 poolside area with lounge chairs and umbrellas, overlooking a scenic landscape.

10. Locanda agli Amici

Locanda agli Amici
Cortona
$97
$116 total
includes taxes & fees
Oct 11 - Oct 12
Locanda agli Amici
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.
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 table set for a tea service with a tiered tray of pastries, a teapot, and various cups and saucers.

11. Hotel Villa Marsili

Hotel Villa Marsili
Cortona Old Town
$199
$228 total
includes taxes & fees
Oct 10 - Oct 11
Hotel Villa Marsili
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 historic stone building with a sign reading "Hotel Italia."
A lobby with a reception desk, a fireplace, and a large arched doorway leading outside.

12. Hotel Italia

Hotel Italia
Cortona Old Town
$113
$127 total
includes taxes & fees
Nov 4 - Nov 5
Hotel Italia
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.

13. Hotel San Luca

Hotel San Luca
Cortona Old Town
$81
$98 total
includes taxes & fees
Oct 28 - Oct 29
Hotel San Luca
A stone building with a rustic charm, featuring a welcoming entrance and a small outdoor seating area.
A swimming pool with a stone wall and potted plants, surrounded by greenery and a clear sky.
A restaurant with a long communal table, wooden chairs, stone walls, and various kitchen utensils displayed on the walls.
A bedroom with a bed, a table with lemons, a window with curtains, and a radiator.

14. Locanda del Molino

Locanda del Molino
Cortona
$77
$94 total
includes taxes & fees
Oct 27 - Oct 28
Locanda del Molino
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 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.

15. Hotel San Michele

Hotel San Michele
Cortona Old Town
$142
$161 total
includes taxes & fees
Nov 2 - Nov 3
Hotel San Michele
A building with multiple floors, a staircase leading to the entrance, and a small garden area with a palm tree and bushes.
A buffet table with various food items, including cookies, pastries, and dairy products, with labels indicating gluten-free options.
A balcony with potted plants and a view of the sea.
A multi-story building with a rooftop terrace featuring outdoor seating and umbrellas.

16. Villa Santa Margherita

Villa Santa Margherita
Cortona Old Town
$108
$141 total
includes taxes & fees
Oct 31 - Nov 1
Villa Santa Margherita
A terrace with sun loungers, stone walls, and potted plants.
A pool area with lounge chairs, a hot tub, and a view of 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.

17. Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa
Cortona Old Town
$248
$282 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 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.

18. Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux
Cortona
$385
$428 total
includes taxes & fees
Nov 2 - Nov 3
Il Falconiere - Relais e Chateaux
Restaurant
Front of property
Room
Reception

19. Agriturismo Parco Fiorito

Agriturismo Parco Fiorito
Tuoro sul Trasimeno
$111
$169 total
includes taxes & fees
Oct 22 - Oct 23
Agriturismo Parco Fiorito
A stone building with multiple windows and a central entrance.
A narrow stone pathway leading to a stone archway, surrounded by lush greenery and a stone wall.
A hotel room with a bed, a yellow armchair, a stone wall, and a window with a lamp.
A terrace with a sofa and cushions, overlooking a cityscape and mountains.

20. Fondaco del Moro

Fondaco del Moro
Civitella in Val di Chiana
$69
$76 total
includes taxes & fees
Oct 6 - Oct 7
Fondaco del Moro
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Go beyond your typical stay in Castiglion Fiorentino

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Pet friendly
Pet friendly
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Hot tub
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Apart hotel
Apart hotel
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Cottage
Cottage
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

October

High 19°C / low 10°C. Sunny most days.
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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.
See properties

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

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 multi-story building with green shutters, a balcony, and a sign with a musical note.

Bed & Breakfast Viziottavo

Bed & Breakfast Viziottavo
Castiglion Fiorentino

10/10 Exceptional

United States
Anonymous traveler
Bed & Breakfast Viziottavo
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.

San Michele al Castello

San Michele al Castello
Castiglion Fiorentino

10/10 Exceptional

United States
Jeff
San Michele al Castello
A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.
A couple in a hot tub with a bottle of champagne and a flower vase.
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.

San Michele al Borgo

San Michele al Borgo
Castiglion Fiorentino

10/10 Exceptional

United States
Vern
San Michele al Borgo
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 modern design, featuring a prominent green sign, multiple balconies, and well-maintained landscaping.
A modern bar area with a counter, bar stools, and a seating area with chairs.

Hotel Park

Hotel Park
Castiglion Fiorentino

10/10 Exceptional

United States
Jean
Hotel Park
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 skylight with a view of a tree and a distant building.
A long dining table set with plates, glasses, and floral centerpieces, surrounded by chairs.

La Cantina Relais - Fattoria Il Cipresso

La Cantina Relais - Fattoria Il Cipresso
Arezzo

10/10 Exceptional

United States
Steve
La Cantina Relais - Fattoria Il Cipresso
A building with multiple floors, a staircase leading to the entrance, and a small garden area with a palm tree and bushes.
A buffet table with various food items, including cookies, pastries, and dairy products, with labels indicating gluten-free options.
A balcony with potted plants and a view of the sea.
A multi-story building with a rooftop terrace featuring outdoor seating and umbrellas.

Villa Santa Margherita

Villa Santa Margherita
Cortona Old Town

10/10 Exceptional

United States
George F
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.
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 table set for a tea service with a tiered tray of pastries, a teapot, and various cups and saucers.

Hotel Villa Marsili

Hotel Villa Marsili
Cortona Old Town

10/10 Exceptional

United States
Kim
Hotel Villa Marsili
A terrace with sun loungers, stone walls, and potted plants.
A pool area with lounge chairs, a hot tub, and a view of 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.

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa
Cortona Old Town

10/10 Exceptional

United States
Eric
Monastero di Cortona Hotel & Spa
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 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.

Cortona Resort - Le Terre Dei Cavalieri

Cortona Resort - Le Terre Dei Cavalieri
Cortona

10/10 Exceptional

United States
Mario
Cortona Resort - Le Terre Dei Cavalieri
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 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 poolside area with lounge chairs and umbrellas, overlooking a scenic landscape.

Locanda agli Amici

Locanda agli Amici
Cortona

10/10 Exceptional

United States
Evangeliste
Locanda agli Amici
A table set with a bottle of wine, two wine glasses, and a vase with flowers.
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.
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.

Poggio Paradiso Resort & Spa

Poggio Paradiso Resort & Spa
Torrita di Siena

10/10 Exceptional

United States
Paul
Poggio Paradiso Resort & Spa
A room with a piano, stone walls, a wooden cabinet, and a bench.
A wooden console table with a mirror above it, a vase with flowers, and a basket of fruit.
A bedroom with a bed, a nightstand, a potted plant, and a window with a view.
A narrow stairway with a small window overlooking a courtyard with a brick building and a wooden ceiling.

Antico Granaione

Antico Granaione
Rapolano Terme

10/10 Exceptional

United States
Irene
Antico Granaione
A stone building with outdoor seating and a pool in the background.
A stone house with a paved driveway and a lawn, surrounded by trees and a white car parked in front.
A dining table set with various foods, including meats, cheeses, and fruits.
A swimming pool with a breakfast tray of fruits and juice, surrounded by trees and a clear sky.

B&B Country House Poggio del Drago

B&B Country House Poggio del Drago
Civitella in Val di Chiana

10/10 Exceptional

United States
Kristen
B&B Country House Poggio del Drago
A view from a window overlooking a green landscape with trees and distant hills.
A modern hotel lobby with orange walls, wooden ceiling, and a central seating area with sofas and tables.
A buffet table with various food items and a wall-mounted rack with kitchen utensils.
A bar area with three stools, a counter with bottles, and a decorative wall with a 'BAR' sign.

Albergo Villa Gaia

Albergo Villa Gaia
Chianciano Terme

10/10 Exceptional

United States
weixing
Albergo Villa Gaia
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.

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World
Cortona

10/10 Exceptional

United States
Anonymous traveler
Villa di Piazzano - Small Luxury Hotel of the World
A cozy wooden cabin room with a bed, pillows, a TV, and a view of the outdoors.
A buffet with various food items and a mirror reflecting the room's architecture.
A stone-walled room with a stone bench, a bathtub with a pink light, and a window with a view.
A modern indoor pool area with wooden benches, a hot tub, and large windows offering views of the surrounding greenery.

I Capricci di Merion Resort & Spa

I Capricci di Merion Resort & Spa
Tuoro sul Trasimeno

10/10 Exceptional

United States
Israel
I Capricci di Merion Resort & Spa
An aerial view of a vineyard estate with rows of grapevines, a swimming pool, and a red building.
An outdoor dining area with string lights, tables set for a meal, and a natural backdrop.
A traditional room with a fireplace, wooden furniture, and a large mirror.
A window with a view of a green landscape, a table with a teapot, cups, and a tray of snacks.

Podere La Rocca

Podere La Rocca
Montepulciano

10/10 Exceptional

United States
B
Podere La Rocca
A hot tub with two glasses of white wine and a plate of strawberries and roses.
A richly decorated room with ornate wallpaper, a chandelier, and classic furniture.
A breakfast setup with a variety of pastries, a bottle of champagne, and glasses on a table in a room with a bed and decorative wall sconces.
A room with ornate ceiling, a chandelier, a sofa, chairs, a table, and a patterned rug.

Residenza Dei Ricci Relais

Residenza Dei Ricci Relais
Chiusi

10/10 Exceptional

United States
Tim
Residenza Dei Ricci Relais
A pool surrounded by lavender and yellow flowers, with a stone wall and a building in the background.
A large estate with a central building, expansive fields, and a well-maintained garden.
An outdoor patio with a table set for dining, surrounded by brick pillars and a view of a garden.
A grand staircase with ornate balustrades, a high ceiling with decorative moldings, and a large painting on the wall.

Podere San Giuseppe

Podere San Giuseppe
Castiglione del Lago

10/10 Exceptional

United States
Timothy
Podere San Giuseppe

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.