
Castiglion Fiorentino Vacations from $681
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Castiglion Fiorentino Vacation
There's no better way to travel than with one of our vacation packages to Castiglion Fiorentino. The rich history and spectacular views are just two of the convincing reasons to visit this captivating city. If sightseeing is on the agenda during your trip to Castiglion Fiorentino, stop by top attractions like Villa Bramasole, Piazza della Repubblica and Cathedral of Cortona. Whoever you're taking time off with and whatever you want to spend, your ultimate Castiglion Fiorentino vacation is just clicks away with Expedia.
The Latest Castiglion Fiorentino vacation packages

Aurum Uffizi
Reviewed on Nov 11, 2025

The Moon Boutique Hotel & Spa
Reviewed on Nov 9, 2025

Hotel Duomo Firenze
Reviewed on Nov 11, 2025


25hours Hotel Florence Piazza San Paolino
Reviewed on Nov 3, 2025
Discover the most popular places to visit in Castiglion Fiorentino
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.
Agricola Buccelletti Winery
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.
Cassero Tower
Find out about the history of Castiglion Fiorentino when you spend time at Cassero Tower. You can enjoy the wineries while in the area.
What to do in Castiglion Fiorentino

Montepulciano Wine Tasting in the Tuscan Countryside

Oil museum and oil mill in Tuscany: tour and tasting

Montepulciano: Wine Tour and tasting
Castiglion Fiorentino Hotel Deals

Farmhouse in the hills with panoramic view and swimming pool
Was wonderful and beautiful.
Reviewed on Nov 30, 2024

Hotel Relais II Chiostro di Pienza
The room was beautiful and very clean. Breakfast staff was very kind.
Reviewed on Oct 29, 2025

Hotel Continentale
We had a last-minute stay there due to the train strike, and it was a great evening after all… The hotel was right there in the main Square plus near the train station. The staff was lovely and they have the most beautiful rooftop patio and bar. you have to check out.
Reviewed on Oct 17, 2025
Find the Best Castiglion Fiorentino Vacation Packages
Castiglion Fiorentino Essential Information
Language | Italian |
|---|---|
Currency | Euros |
Local Welcome | Ciao |
Local Goodbye | Ciao |
Population | 8,300 |
Max Temp Winter | 45ºF |
Max Temp Summer | 80ºF |
Top Sights | Cathedral of Saints Peter and Donato, Signorelli Theatre and Cathedral of Cortona |
More vacations you might like
Frequently asked questions
Explore a world of travel with Expedia
- Pievuccia Hotels
- Hotels near Agricola Buccelletti Winery
- Gay friendly Hotels in Rigutino
- Rigutino Hotels
- San Pietro a Cegliolo Hotels
- Apartments in Sodo
- Town Houses in Sodo
- Hotels near Eremo Le Celle
- Hotels near Signorelli Theatre
- Cortona Hotels
- Villas in Cortona
- Apartments in Cortona
- Hotel Wedding Venues Hotels in Cortona
- Gay friendly Hotels in Cortona
- Winery Hotels in Cortona
- Farmstay in Cortona
- B&B in Cortona
- Resorts & Hotels with Spas in Cortona
- Ski Hotels in Cortona
- Hotels with Restaurants in Cortona
- 5 Star Hotels in Cortona
- Hotels with a View in Cortona
- Historic Hotels in Cortona
- Luxury Hotels in Cortona
- Relais & Chateaux Hotels in Cortona
- Extended Stay Hotels in Cortona
- Beach Hotels in Cortona
- Hotels with a Pool in Cortona
- Casino Hotels in Cortona
- Hotels & Resorts for Couples in Cortona
- Town Houses in Cortona
- Honeymoon Resorts & in Cortona
- Hotels with Tennis Courts in Cortona
- Cheap Hotels in Cortona
- Golf Hotels in Cortona
- 4 Star Hotels in Cortona
- Hotels with Free Parking in Cortona
- Hotels with Childcare in Cortona
- Family Hotels in Cortona
- 3 Star Hotels in Cortona
- Villas in Cesa
- Cesa Hotels
- Historic Hotels in Cortona Old Town
- Hotels near Cortona Old Town
- Hotels with Free Parking in Cortona Old Town
- Beach Hotels in Cortona Old Town
- Hotels with Restaurants in Cortona Old Town
- Hotels with Balconies in Cortona Old Town
- Hotels with Fireplaces in Cortona Old Town
- Municipal Art Gallery
- Cassero Tower
- Tennis Club Castiglionese
- Visit Poggiolo
- Casa del Re Vacations
- La Strada-Santa Cristina Vacations
- Agricola Buccelletti Winery
- Visit La Strada-Santa Cristina
- Visit Castroncello
- Visit Rigutino
- Il Borgo Vacations
- Visit San Pietro a Cegliolo
- Visit Polvano
- Visit Sodo
- Eremo Le Celle
- Santa Maria Nuova
- Signorelli Theatre
- Museum of the Etruscan Academy
- Casali Palace
- Palazzo Comunale
- Piazza della Repubblica
- Cortona Vacations
- Santa Margherita Basilica
- Visit Cortona
- Where to stay in Cortona
- Fortress of Girifalco
- Villa Bramasole
- Visit Montagnano
- Visit Cesa
- Visit Cortona Old Town
- Car rentals near Sodo
- Car rentals near Cortona
- Sixt Rental Cars in Cortona
- Hertz Rental Cars in Cortona
- Van Car Rentals in Cortona
- Europcar Rental Cars in Cortona
- Avis Rental Cars in Cortona
- Enterprise Rental Cars in Cortona
- Budget Rental Cars in Cortona
- Luxury Car Rentals in Cortona
- Greenmotion Rental Cars in Cortona
- National Car Rental Rental Cars in Cortona
- Convertible Car Rentals in Cortona
- Car rentals near Santa Margherita Basilica
- Car rentals near Cortona Old Town



















