Castiglion Fiorentino Holiday Rentals, Tuscany: Private House Rentals

A historic town with a prominent church tower, surrounded by rolling hills and vineyards.

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Our top choices for Castiglion Fiorentino hotels

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

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

A couple in a bathtub with candles, suggesting a romantic setting.

A stone building with a grassy courtyard, a staircase, and a small garden area.

1. San Michele al Castello

Castiglion Fiorentino

Alejandro

2.924.965 ₫

3.333.249 ₫ total

includes taxes & fees

28 Oct - 29 Oct

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 hotel with a modern design, featuring a prominent green sign, multiple balconies, and well-maintained landscaping.

2. Hotel Park

Castiglion Fiorentino

Karen

2.723.651 ₫

3.111.804 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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.

3. San Michele al Borgo

Castiglion Fiorentino

Vern

3.631.535 ₫

4.110.476 ₫ total

includes taxes & fees

28 Oct - 29 Oct

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

A bedroom with a dark-colored bed, wooden ceiling beams, a white bedside table, and a wall-mounted light fixture.

4. Bed & Breakfast Viziottavo

Castiglion Fiorentino

luigi

2.236.815 ₫

3.155.225 ₫ total

includes taxes & fees

24 Nov - 25 Nov

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 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.

5. La Cantina Relais - Fattoria Il Cipresso

Arezzo

erik

2.555.627 ₫

2.984.871 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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 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.

6. Il Falconiere - Relais e Chateaux

Cortona

Qingwen

9.485.411 ₫

10.549.740 ₫ total

includes taxes & fees

15 Nov - 16 Nov

A terrace with sun loungers, stone walls, and potted plants.

A spacious lobby with a high ceiling, a grand chandelier, and a staircase leading to an upper level.

A narrow hallway with a stone wall and a clock.

A historic town with traditional architecture, a central courtyard with a swimming pool, and a view of distant mountains.

7. Monastero di Cortona Hotel & Spa

Cortona Old Town

MICHELLE

7.030.113 ₫

7.848.912 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

8. Hotel San Luca

Cortona Old Town

Frances

2.318.186 ₫

2.665.996 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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 nighttime swimming pool with a clear reflection, surrounded by trees and lounge chairs.

An outdoor dining area with tables set for breakfast, including pastries, fruit, and beverages.

9. Hotel Le Capanne

Arezzo

Ronilynn

2.731.324 ₫

3.178.139 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

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.

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

10. Hotel San Michele

Cortona Old Town

Asha

3.106.218 ₫

3.532.628 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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 hallway with a decorative archway leading to a door, a row of plants on the left, and a wall-mounted lamp on the right.

A rooftop terrace with outdoor seating, a pergola, and a view of hills.

11. Il Gentiluomo Hotel & SPA

Arezzo

Luis Mauricio

1.871.030 ₫

2.231.815 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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 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.

12. Hotel Italia

Cortona Old Town

Fernando

2.924.965 ₫

3.289.829 ₫ total

includes taxes & fees

23 Nov - 24 Nov

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a stone building in the background.

An outdoor dining area with tables set for a meal, surrounded by greenery and trees.

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.

13. Villa di Piazzano - Small Luxury Hotel of the World

Cortona

lynda

17.598.469 ₫

19.589.892 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A spacious breakfast room with a modern design, featuring a herringbone floor pattern, comfortable seating, and a staircase leading to other areas.

A modern hotel room with a desk, chair, and a bed.

A bar area with a wooden counter, seating, and large windows.

A modern bathroom with a bench, a shower with a handheld showerhead, and a window.

14. Hotel Minerva

Arezzo

Fabienne

2.526.285 ₫

2.952.595 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A building with a stone pathway leading to an arched entrance, flanked by potted plants and lit by ground lights.

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

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.

15. Hotel Villa Marsili

Cortona Old Town

fares

5.968.348 ₫

6.680.971 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A balcony with a table set for breakfast, overlooking a cityscape with historic buildings and a river.

A lobby with a reception desk, a staircase, a bar area, and a seating area with a potted plant.

A room with a white tufted sofa set, a marble coffee table, and a stained glass window.

A hotel with a classic architectural style, featuring a ground floor with a large entrance and a visible restaurant sign.

16. Hotel Continentale

Arezzo Centro Storico

Thanh

2.964.841 ₫

3.551.306 ₫ total

includes taxes & fees

26 Oct - 27 Oct

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

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.

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

17. Locanda agli Amici

Cortona

David

2.611.737 ₫

2.988.699 ₫ total

includes taxes & fees

3 Nov - 4 Nov

A historic town with a prominent church, a square with outdoor seating, and a swimming pool.

A hotel room with a bed, two bedside lamps, a window with curtains, and framed pictures on the wall.

A room with a herringbone floor, a bed, a sofa, a desk, and a view through a window.

A terrace with a table set for breakfast, overlooking a scenic landscape.

18. Relais Cloister Pienza

Pienza

Karen

3.315.881 ₫

3.821.151 ₫ total

includes taxes & fees

29 Oct - 30 Oct

19. Agriturismo Parco Fiorito

Tuoro sul Trasimeno

Anonymous traveller

2.921.835 ₫

4.418.214 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A grand banquet hall with ornate ceiling, long tables set for a formal event, and elaborate floral centerpieces.

A large pool with a curved edge, surrounded by a courtyard with a building featuring arched windows and columns.

A historic stone building with arched doorways and a courtyard at twilight.

A long banquet table with gold candelabras, white flowers, and gold tableware.

20. Relais La Corte dei Papi

Cortona

Frithjof

8.376.612 ₫

9.330.061 ₫ total

includes taxes & fees

10 Nov - 11 Nov

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Stay near popular Castiglion Fiorentino attractions

Tennis Club Castiglionese

Catch an event at Tennis Club Castiglionese during your trip to Castiglion Fiorentino. You can enjoy the wineries while in the area.

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Cassero Tower

9.4/10 (6 reviews)

Find out about the history of Castiglion Fiorentino when you take a trip to Cassero Tower. You can enjoy the wineries while in the area.

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Agricola Buccelletti Winery

10.0/10 (2 reviews)

You can enjoy a tasting or tour at Agricola Buccelletti Winery during your travels to La Strada-Santa Cristina. Discover the area's countryside and wineries.

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Archaeological Museum

9.6/10 (5 reviews)

You can browse the exhibits at Archaeological Museum, a museum with a storied past, during your travels to Castiglion Fiorentino. You can enjoy the wineries while in the area.

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Vasari Loggia

10.0/10 (2 reviews)

You can find out about the history of Castiglion Fiorentino with a trip to Vasari Loggia. You can enjoy the wineries while in the area.

See properties

Learn more about Castiglion Fiorentino

Climb the medieval walls of this hilltop town for sweeping views across Tuscany's Val di Chiana countryside. Explore the Etruscan Archaeological Museum inside Palazzo Casali, then enjoy aperitivo with locals in Piazza del Municipio.

See all hotels in Castiglion Fiorentino

Top Castiglion Fiorentino Hotel Reviews

Hotel Corsignano

8/10 Good

"Room was clean and staff was courteous and attentive"

Hotel San Gregorio

10/10 Excellent

"Beautiful property with wonderful staff and food. Highly recommend."

Nuovo Etruria Resort

8/10 Good

"When we arrived the gate to the hotel was locked. Called the hotel and then a person drove up and helped us to check in. He was very nice. The hotel is very old, but a decent place to stay for a night."

Relais Villa Grazianella - UNA Esperienze

10/10 Excellent

"Absolutely beautiful! Astonishing views! If you are looking for peace and quiet with great service this is the place."

Monastero di Cortona Hotel & Spa

10/10 Excellent

"Amazing service and care. Especially Sara, Mathilda, Fredrico and Allesandro. The manager was so helpful as well. A must stay!"

Hotel Villa Ricci

10/10 Excellent

"It's a lovely hotel, but it is the staff that make it truly special. Attentive and cheerful, I felt well looked after from the moment I walked in. Wonderful stay, I'll definitely be back."

Hotel Minerva

8/10 Good

"Very good restaurant. Mattresses could be more comfortable and rooms are not soundproofed, but we would come back because it is a good hotel, excellent breakfast and big rooms."

Hotel Continentale

10/10 Excellent

"The location of this hotel is excellent!"

Hotel Panoramic Montepulciano

8/10 Good

"Ok."

More cheap stays in Castiglion Fiorentino

Hotel Chenno

Via Don Lorenzo Boschi 29 Subbiano AR

1.184.222 ₫

1.389.456 ₫ total

25 Oct - 26 Oct

includes taxes & fees

Hotel La Terrazza di Montepulciano

Via Pié al Sasso 16 Montepulciano SI

2.894.701 ₫

3.299.959 ₫ total

25 Oct - 26 Oct

includes taxes & fees

9.4/10 Exceptional! (218 reviews)

Locanda Granducato

località paccianese 48 Chiusi SI

3.540.746 ₫

3.952.714 ₫ total

26 Oct - 27 Oct

includes taxes & fees

7/10 Good! (2 reviews)

La Locanda di Casalmustia

Piazza della Pieve 3 Trequanda SI

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8.6/10 Excellent! (44 reviews)

Tenuta La Pieve Casale Presciano

Via di Migliari Pergine Valdarno AR

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Tenuta La Pieve Casale La Valle

Via Giovanni XXII Pergine Valdarno AR

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Hotels in Castiglion Fiorentino with star rating

Frequently asked questions

What's the seasonal weather like in Castiglion Fiorentino?

The hottest months are usually August and July, with an average temperature of 22°C, while the coldest months are January and February, with an average of 6°C. Average annual precipitation for Castiglion Fiorentino is 901 mm.

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Book Hotels in Castiglion Fiorentino on Expedia.it

Find hotels in Castiglion Fiorentino from 1.389.456 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Castiglion Fiorentino

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Castiglion Fiorentino hotels

1. San Michele al Castello

2. Hotel Park

3. San Michele al Borgo

4. Bed & Breakfast Viziottavo

5. La Cantina Relais - Fattoria Il Cipresso

6. Il Falconiere - Relais e Chateaux

7. Monastero di Cortona Hotel & Spa

8. Hotel San Luca

9. Hotel Le Capanne

10. Hotel San Michele

11. Il Gentiluomo Hotel & SPA

12. Hotel Italia

13. Villa di Piazzano - Small Luxury Hotel of the World

14. Hotel Minerva

15. Hotel Villa Marsili

16. Hotel Continentale

17. Locanda agli Amici

18. Relais Cloister Pienza

19. Agriturismo Parco Fiorito

20. Relais La Corte dei Papi

Stay near popular Castiglion Fiorentino attractions

Tennis Club Castiglionese

Cassero Tower

Agricola Buccelletti Winery

Archaeological Museum

Vasari Loggia

Learn more about Castiglion Fiorentino

Top Castiglion Fiorentino Hotel Reviews

Hotel Corsignano

Hotel San Gregorio

Nuovo Etruria Resort

Relais Villa Grazianella - UNA Esperienze

Monastero di Cortona Hotel & Spa

Hotel Villa Ricci

Hotel Minerva

Hotel Continentale

Hotel Panoramic Montepulciano

More cheap stays in Castiglion Fiorentino

Hotel Chenno

Hotel La Terrazza di Montepulciano

Locanda Granducato

La Locanda di Casalmustia

Tenuta La Pieve Casale Presciano

Tenuta La Pieve Casale La Valle

Hotels in Castiglion Fiorentino with star rating

Frequently asked questions

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