Hotels logo

Hotels in Castiglion Fiorentino

October 2026
7
November 2026

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

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

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

San Michele al Castello
Castiglion Fiorentino
$114
$130 total
includes taxes & fees
Oct 19 - Oct 20
San Michele al Castello
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

Hotel Park
Castiglion Fiorentino
$106
$121 total
includes taxes & fees
Oct 20 - Oct 21
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
$87
$123 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 spa area with a reception desk, a chair, and a wall with a logo.
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
$141
$159 total
includes taxes & fees
Oct 19 - Oct 20
San Michele al Borgo
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 Resort - Le Terre Dei Cavalieri
Cortona
$150
$170 total
includes taxes & fees
Oct 8 - Oct 9
Cortona Resort - Le Terre Dei Cavalieri
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
$95
$112 total
includes taxes & fees
Oct 14 - Oct 15
La Cantina Relais - Fattoria Il Cipresso
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

Relais Villa Baldelli
Cortona
$117
$138 total
includes taxes & fees
Oct 8 - Oct 9
Relais Villa Baldelli
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

Villa Borgo San Pietro
Cortona
$125
$147 total
includes taxes & fees
Oct 15 - Oct 16
Villa Borgo San Pietro
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

Locanda agli Amici
Cortona
$97
$116 total
includes taxes & fees
Oct 13 - Oct 14
Locanda agli Amici
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

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

B&B San Francesco
Cortona Old Town
$81
$111 total
includes taxes & fees
Oct 18 - Oct 19
B&B San Francesco
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

Hotel San Michele
Cortona Old Town
$135
$157 total
includes taxes & fees
Oct 8 - Oct 9
Hotel San Michele
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

Hotel Villa Marsili
Cortona Old Town
$218
$249 total
includes taxes & fees
Oct 10 - Oct 11
Hotel Villa Marsili
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

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 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

Locanda del Molino
Cortona
$77
$93 total
includes taxes & fees
Oct 27 - Oct 28
Locanda del Molino
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

Il Falconiere - Relais e Chateaux
Cortona
$385
$429 total
includes taxes & fees
Nov 2 - Nov 3
Il Falconiere - Relais e Chateaux
A building with multiple floors, a staircase leading to the entrance, and a small garden area with a palm tree and bushes.
A rooftop terrace with outdoor furniture, a large umbrella, and a view of the landscape.
A patio with wicker furniture and a large umbrella, overlooking a building with multiple windows and a staircase.
A hotel room with three beds, a television, a mirror, and a bedside table with a lamp.

17. 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 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

Monastero di Cortona Hotel & Spa
Cortona Old Town
$247
$281 total
includes taxes & fees
Oct 25 - Oct 26
Monastero di Cortona Hotel & Spa
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

Fondaco del Moro
Civitella in Val di Chiana
$69
$76 total
includes taxes & fees
Oct 9 - Oct 10
Fondaco del Moro
Restaurant
Exterior
Room
Front of property

20. Agriturismo Parco Fiorito

Agriturismo Parco Fiorito
Tuoro sul Trasimeno
$111
$169 total
includes taxes & fees
Oct 22 - Oct 23
Agriturismo Parco Fiorito
View all properties

Go beyond your typical stay in Castiglion Fiorentino

pet friendly image
Pet friendly
Pet friendly
Pool image
Pool
Pool
hot tub image
Hot tub
Hot tub
spa image
Spa
Spa
apart-hotel image
Apart hotel
Apart hotel
Apartment image
Apart­ment
Apart­ment
Family friendly image
Family friendly
Family friendly
Condo image
Condo
Condo
villa image
Villa
Villa
Cottage image
Cottage
Cottage
Resort image
Resort
Resort
farm image
Farm
Farm
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.
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.
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.
See properties

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.
See properties

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.
See properties

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.
See properties

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 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

10/10 Exceptional

United States
Anonymous traveler
Bed & Breakfast Viziottavo
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.

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 breakfast setting with a fireplace, a table with plates, glasses, and a croissant.
A spa area with a reception desk, a chair, and a wall with a logo.
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 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.

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 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.

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 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.

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 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.

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 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.

Villa Santa Margherita

Villa Santa Margherita
Cortona Old Town

10/10 Exceptional

United States
George F
Villa Santa Margherita
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.

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 room with a bed, a pink suit, a handbag, and yellow shoes.
A corridor with a large arched doorway, a white door labeled "202", and a sofa with a geometric pattern.
A room with a glass floor, stone walls, and a door in the center.
A pathway flanked by lush greenery and palm trees, leading to a building with large glass windows.

SUGAR ROOMS Residenza d' Epoca

SUGAR ROOMS Residenza d' Epoca
Arezzo Centro Storico

10/10 Exceptional

United States
Sharon
SUGAR ROOMS Residenza d' Epoca
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.

Locanda agli Amici

Locanda agli Amici
Cortona

10/10 Exceptional

United States
Evangeliste
Locanda agli Amici
A room with a piano, stone walls, a wooden cabinet, and a bench.
A bedroom with a bed, a nightstand, a potted plant, and a window with a view.
A dining area with a yellow table, white chairs, and a kitchen in the background.
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 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 hallway with a checkered floor, arched windows, and a chandelier.
A buffet with various food items, a vase of flowers, and a mirror reflecting the room.

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 modern indoor pool area with wooden benches, a hot tub, and large windows offering views of the surrounding greenery.
A gravel pathway flanked by neatly trimmed hedges leading to a gate.
A buffet with various food items and a mirror reflecting the room's architecture.

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
A large estate with multiple buildings, a well-maintained garden, and a vineyard in the background.
A dining area with a brick archway, tables set for dining, and a fireplace.
An outdoor patio with brick arches, wicker furniture, and hanging lanterns.
A pool with a view of a hillside.

Lupaia

Lupaia
Torrita di Siena

10/10 Exceptional

United States
KC Traveler
Lupaia
A view from a window overlooking a green landscape with trees and distant hills.
A buffet table with various food items and a wall-mounted rack with kitchen utensils.
A modern hotel lobby with orange walls, wooden ceiling, and a central seating area with sofas and tables.
A modern living room with a white sofa, orange cushions, a wooden coffee table, and a bookshelf with decorative items and books.

Albergo Villa Gaia

Albergo Villa Gaia
Chianciano Terme

10/10 Exceptional

United States
weixing
Albergo Villa Gaia
An aerial view of a vineyard estate with rows of grapevines, a swimming pool, and a red building.
A window with a view of a green landscape, a table with a teapot, cups, and a tray of snacks.
An outdoor dining area with string lights, tables set for a meal, and a natural backdrop.
A bedroom with a large bed, wooden headboard, a chandelier, a nightstand, and a red rug.

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 garden pathway leading to a building with a yellow facade and arched windows.
A room with ornate ceiling, a chandelier, a sofa, chairs, a table, and a patterned rug.
A richly decorated room with ornate wallpaper, a chandelier, and classic furniture.

Residenza Dei Ricci Relais

Residenza Dei Ricci Relais
Chiusi

10/10 Exceptional

United States
Tim
Residenza Dei Ricci Relais

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.