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

Historic Hotels & Resorts in Castiglion Fiorentino from AU$143

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Castiglion Fiorentino Historic Hotels

Tonight
25 Sept - 26 Sept
Tomorrow
26 Sept - 27 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

Our top choices for Castiglion Fiorentino historic hotels

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 standing at the entrance of a building with a stone staircase leading up to a door.
A person in a swimming pool with a view of trees and mountains through a window.

1. Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux
Cortona
United States
Qingwen
AU$685
includes taxes & fees
26 Oct - 27 Oct
Il Falconiere - Relais e Chateaux
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 bathroom with a bathtub, a table with a vase of flowers, and a view of the countryside through a window.

2. Hotel San Michele

Hotel San Michele
Cortona Old Town
United States
Tala
AU$254
includes taxes & fees
8 Oct - 9 Oct
Hotel San Michele
A hotel room with a wooden ceiling, a large bed with a blue headboard, a TV, a jacuzzi, and a bottle of champagne.
A hotel entrance with a wooden door, a potted plant, a wall-mounted light fixture, and a brass doorbell.
A dining area with green upholstered chairs, a checkered floor, and a view of the outdoors through large windows.
A hotel entrance with a stone facade, a sign for room number 23, and two potted plants with red ribbons.

3. Graziella Patio Hotel

Graziella Patio Hotel
Arezzo Centro Storico
United States
James
AU$292
includes taxes & fees
1 Oct - 2 Oct
Graziella Patio Hotel
A staircase with two lit lanterns on the wall.
A dining area with a wooden table, chairs, and a mirror. There is a clock on the wall and a window with a view.
A balcony with a potted plant and a metal railing.
A cozy living room with a mirrored wall, a sofa with a red heart pillow, a lamp, and a clock on the wall.

4. Cortona Shabby Chic House<br>(Independent & balcony)

Cortona Shabby Chic House<br>(Independent & balcony)
Cortona Old Town
United States
Erin
Cortona Shabby Chic House<br>(Independent & balcony)
A view from a window overlooking a courtyard with stone buildings and a tower.
A kitchen with white cabinets, a stove, and a chandelier.
A bedroom with a bed, two chairs, a table, a lamp, and a clock.
A spacious living area with a dining table, white chairs, a sofa, and a chandelier.

5. La Finestra sul Teatro

La Finestra sul Teatro
Cortona Old Town
United States
Michelle H.
AU$309
includes taxes & fees
29 Sept - 30 Sept
La Finestra sul Teatro
A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.
A historic stone building with a tower, surrounded by a well-maintained garden with flowering plants.
A banquet hall with round tables set for a formal event, featuring a stone fireplace and large windows.
A cozy room with a fireplace, wooden beams, a ladder, and a table with a bowl of fruit.

6. Castello di Gargonza

Castello di Gargonza
Monte San Savino
Canada
Iain
AU$375
includes taxes & fees
28 Sept - 29 Sept
Castello di Gargonza
A balcony with a clear view of a distant landscape, a stone building, and a glass of orange juice.
A kitchen with a gas stove, a kettle, and a table with a plant and candles.
A building with a tiled roof and a bell tower.
A room with a view of a balcony, a white chair, a flower vase, and a towel with flowers.

7. Cortonas Rooftop Nest

Cortonas Rooftop Nest
Cortona Old Town
United States
Robin F.
Cortonas Rooftop Nest
An arched doorway leading to a building with a wooden door and a staircase.
A cozy living room with a fireplace, comfortable seating, and a decorative mirror.
A rustic room with a stone floor, wooden beams, a fireplace, and shelves with various items.
A balcony with a view of a town, including a church tower and distant mountains.

8. Residenza Fabroni

Residenza Fabroni
Montepulciano
United States
Nicholas
AU$143
includes taxes & fees
5 Oct - 6 Oct
Residenza Fabroni
A stone building with a balcony, surrounded by lush greenery and flowering plants.
A cozy room with a wooden bench, a colorful rug, and a view of greenery through an arched window.
A stone house with a sloped roof, a wooden porch, and a garden with various plants and flowers.
An outdoor seating area with two wooden chairs and a potted plant with red flowers.

9. Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
Canada
Paul Q.
AU$253
includes taxes & fees
7 Oct - 8 Oct
Il Poggio dell'Eremita

10. Agriturismo Rocca di Pierle

Agriturismo Rocca di Pierle
Mercatale
AU$298
includes taxes & fees
26 Sept - 27 Sept
Agriturismo Rocca di Pierle
View all properties

Top Castiglion Fiorentino Hotel Reviews

Hotel Corsignano

Hotel Corsignano

10/10 Excellent
"Everything was perfect the staff the hotel."
steve 1-night trip
Posted 10 hours ago
Hotel Corsignano
Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent
"Stunning little hotel with the most beautiful setting, gardens and pool. The room was exceptionally appointed clean. The best part of the stay was the restaurant. The best meals we had on our entire trip. Definitely recommend hiring e-bikes and riding up to Cortona!"
Beren 2-night trip
Posted 5 days ago
Villa di Piazzano - Small Luxury Hotel of the World
Hotel Panoramic Montepulciano

Hotel Panoramic Montepulciano

10/10 Excellent
"buenas vistas panorámicas , es un hotel demasiado tranquilo , pero es muy bonito"
Enzo 2-night trip
Posted 5 days ago
Hotel Panoramic Montepulciano
Hotel San Gregorio

Hotel San Gregorio

8/10 Good
"Quaint but modern hotel walking distance to all - good breakfast and service in hotel restaurant. Spacious rooms with air conditioning (which gets turned off when staff cleans room - call desk to turn back on), safe, and bathroom with tub- but no shower curtain- took a while to learn how to negotiate using the shower handle. Pool area is restful. Enjoyed our stay"
JANET 3-night trip
Posted 7 days ago
Hotel San Gregorio
Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

10/10 Excellent
"We loved this hotel. We were lucky to have a two bedroom apartment. It’s not connected to the hotel, so be prepared to drive 10 minutes each way. The prepared breakfast was wonderful and the staff was always very pleasant."
Eva 2-night trip
Posted 8 days ago
Relais Villa Grazianella - UNA Esperienze
Agriturismo La Sovana

Agriturismo La Sovana

10/10 Excellent
"We absolutely loved our stay at La Sovana! The grounds are impeccably manicured and maintained! The pool was lovely after a long day of sight seeing and we had an incredible time enjoying the dinner one evening. The stay were incredible throughout our stay and so helpful and kind. The owner was on site quite a bit and I think that added to the charm. He introduced himself at the dinner and danced with some guests. It gave it a beautiful family run feel and you could tell he took a lot of pride in his hotel. My husband and I loved the complimentary breakfast buffet. It gave us a great start to the our day of sight seeing in the area. Would return in a heartbeat!"
Raina 3-night trip
Posted 11 days ago
Agriturismo La Sovana
Il Gentiluomo Hotel & SPA

Il Gentiluomo Hotel & SPA

10/10 Excellent
"Everything was OK. Clean room, helpfull staff. Excellent breakfast."
Grzegorz 1-night trip
Posted 12 days ago
Il Gentiluomo Hotel & SPA
Boutique Villa Liberty - Depandance Hotel - Borgo Capitano Collection - Albergo diffuso

Boutique Villa Liberty - Depandance Hotel - Borgo Capitano Collection - Albergo diffuso

10/10 Excellent
"Beautiful and sparkling clean property. Excellent location in walking distance from lovely shops and restaurants. Wonderful staff and the best breakfast of all the properties we have visited!"
Alessio 1-night trip
Posted 1 month ago
Boutique Villa Liberty - Depandance Hotel - Borgo Capitano Collection - Albergo diffuso
Hotel Villa Ricci

Hotel Villa Ricci

10/10 Excellent
"The staff was so incredibly friendly and accommodating. They were ready with recommendations, patient with our lack of Italian knowledge, and always smiling when we entered. The spa is so lovely and relaxing, and reasonably priced. Breakfast spread is lovely and served fairly late into the morning. Walkable to multiple delicious restaurants nearby. We would definitely recommend this hotel if you’re visiting Tuscany."
Amber 2-night trip
Posted 2 months ago
Hotel Villa Ricci

Frequently asked questions

What should I expect on my historical trip to Castiglion Fiorentino?
A visit to the historical sites in Castiglion Fiorentino is likely first on your sightseeing itinerary. You can also explore all there is to see and do including the wineries and churches.
What's the best accommodation in Castiglion Fiorentino to learn about local history?
Beautiful villa in Tuscany with park and panoramic swimming pool! is one of the top choices for history buffs.
How many historical hotels are located in Castiglion Fiorentino?
Castiglion Fiorentino is home to 291 hotels and other accommodation options bookable on Expedia though you won't find many designated historic hotels.
What are the most important historical sites and other places in Castiglion Fiorentino?
Landmarks like Vasari Loggia and Cassero Tower in Castiglion Fiorentino might be worth a visit. A couple of additional sights to add to your itinerary are Val di Chiana and Tennis Club Castiglionese.
What is a historic hotel like in Castiglion Fiorentino?
By booking a historic hotel, guests can spend a night or two someplace that has a national historic designation. A stately home, palace or even a lodge, old police station or skyscraper can be turned into a historic hotel provided that it's a place of special interest. Traditional architecture and period features can be admired within the guestrooms or public spaces of such hotels in Castiglion Fiorentino, giving a sense of history.
What is the difference between a historic hotel and a heritage hotel?
"Heritage hotel" is more common in Asia and Europe, while "historic hotel" is more common in the U.S. overall though the terms are similar. The architecture and actual building of a historic hotel is generally the most important aspect. For a heritage hotel, often it's the cultural value along with how it inspired the community.
Do historic hotels in Castiglion Fiorentino have modern facilities?
Hotels have the safety features and modern conveniences you might expect, while every effort is made to preserve historic facades and treasured traditions. WiFi, heating and air conditioning, updated bathroom facilities, and the usual amenities found at a contemporary hotel should be available at a historic hotel. Rest assured that when you choose a historic hotel in Castiglion Fiorentino, you won't be staying at a place that is rundown or uncomfortable.

Explore a world of travel with Expedia