Castiglion Fiorentino Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 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
Top Flight + Hotel Deals in Castiglion Fiorentino
Price found within the past 48 hours. Click for updated prices.
Glance Hotel In Florence
Historic Centre of Florence
€702
per person
22 Dec - 27 Dec
found 21 hours ago
Return direct flight included
Athens (ATH) to Florence (FLR)
9.4/10 Exceptional! (1,001 reviews)
Florence is a walkable city for most (uneven surfaces) making this a great location. It’s a 7 - 10 minute walk (depending on luggage) from the train station.
Great rooftop pool with great views and service. The Club sandwich is among the best we have ever had. Sunset in the pool was amazing too.
Breakfast was exceptional with great selection and great coffee !
Reviewed on 28 Sept 2026
Plaza Hotel Lucchesi
Historic Centre of Florence
€741
per person
22 Dec - 27 Dec
found 21 hours ago
Return direct flight included
Athens (ATH) to Florence (FLR)
9.4/10 Exceptional! (1,003 reviews)
The hotel’s location is excellent—away from the chaos but still close to the main Florence attractions. We were able to walk almost everywhere, which was very convenient.
The staff was friendly and accommodating, and the rooftop bar, restaurant, and pool were wonderful. The property is very well located and offers some great amenities.
The room was okay, The bathroom, in particular, is poorly designed. It is quite small, yet has a large sink, toilet, and bathtub, leaving very little space to move around. After a shower, there is barely enough room to dry yourself without the towel falling into either the toilet or the sink.
Overall, the location, staff, and rooftop facilities are definite highlights.
Reviewed on 8 Oct 2026
Top hotels in Castiglion Fiorentino
Spacious Tuscan Villa with Large Pool near Castiglion Fiorentino.
Castiglion Fiorentino
9.8/10 Exceptional! (45 reviews)
"La Fenice was wonderful. The property is amazing and in a great location for what we wanted to see in the Tuscan region. The hosts are very accommodating and made our stay special. Looking forward myself to revisiting on my next trip to Tuscany."
Reviewed on 7 Oct 2026
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
€677
12 Oct - 13 Oct
includes taxes & fees
9.8/10 Exceptional! (253 reviews)
"Stunning property; a real representation of Tuscany with the long driveway of tall trees; staff was amazing; food was excellent; gardens, picturesque! We would highly recommend! Overall amazing !!!"
Reviewed on 5 Oct 2026
Precise Tale Poggio Alla Sala
Via Di Poggio Alla Sala, 10 Montepulciano SI
9.6/10 Exceptional! (181 reviews)
"Great, peaceful place to stay. Gorgeous property with pools and spa. Could use another food option but otherwise excellent."
Reviewed on 7 Oct 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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.
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.
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.
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.
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.
What to do in Castiglion Fiorentino
Private Tasting of Organic Wines in the Cellar in Mugliano
€30
per adult
Oil museum and oil mill in Tuscany: tour and tasting
€20
per adult
Frequently asked questions
How much does a Castiglion Fiorentino holiday package cost?
Offering great value package deals from €702 on Expedia, you'll be surprised at how little a holiday to Castiglion Fiorentino costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Castiglion Fiorentino?
To score cheap Castiglion Fiorentino holiday packages, plan your trip outside of peak periods like public holidays and major events. You'll typically find better availability and lower prices in the off-season or when it's less busy.
How many days is enough for Castiglion Fiorentino?
Dedicate at least 3 days for your Castiglion Fiorentino holiday in order to enjoy everything that makes this place special. Explore key areas, including Cortona Old Town and Sodo. Then head to the major sights such as Archaeological Museum and Vasari Loggia. With a clever itinerary, you'll be kept busy with room for some downtime too. Want to venture outside of Castiglion Fiorentino? Consider squeezing in an excursion or two.
Is it worth booking a holiday package to Castiglion Fiorentino?
Well known for its nightlife, views and walking trails, a Castiglion Fiorentino holiday is a hit with all kinds of visitors. Be sure to visit top sights like Cassero Tower and Municipal Art Gallery, and consider renting a car for day trips to explore even more.
How to find the best Castiglion Fiorentino package deals?
Use Expedia's filter tool to help you find some great Castiglion Fiorentino package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Castiglion Fiorentino package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your holiday package well in advance.
Is it cheaper to book a Castiglion Fiorentino holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component separately. And you'll still have the freedom to create a personalised Castiglion Fiorentino holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday package to Castiglion Fiorentino?
If you've got your Castiglion Fiorentino travel dates locked in, book as soon as you can to bag some incredible deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for impromptu escapes.
How to plan a trip to Castiglion Fiorentino?
- Choose when to travel: Check your diary and get your bags packed. Your favourite time of year and the available activities will also help you decide when to holiday in Castiglion Fiorentino.
- Work out your budget: Ensure you have enough money to cover everything from food and transportation to activities and flights. Your accommodation will likely be the biggest expense during your trip to Castiglion Fiorentino.
- Work out your trip length: Think about how much time you want to spend discovering Castiglion Fiorentino. Plan your itinerary so you can get to all the activities and attractions you're interested in without rushing.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a customised Castiglion Fiorentino holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
