Castiglion Fiorentino Holidays

Photo by Sophia Field

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Top Flight + Hotel Deals in Castiglion Fiorentino

Price found within the past 48 hours. Click for updated prices.
Hotel Miceli - Civico 50

Hotel Miceli - Civico 50

3 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
18 Oct - 22 Oct
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
8.8/10 Excellent! (185 reviews)
There was no staff on-site when we arrived, but we had been in touch with the hotel via WhatsApp all day, and they were super helpful and friendly! Entering the building was very easy, but the 3-person elevator was just a little squished. The room was as expected - the only downside was that the shower was only cold water (after running it for a few minutes) and the sink in the bathroom was only hot water! The room was warm when we entered, but we turned the air conditioning up and it was perfect by the time we arrived back for bed. All-in-all, it was a good stay overnight!

Reviewed on 22 Jun 2025

LHP River Club

LHP River Club

5 out of 5
Santa Croce
Save 100% on your flight
per person
18 Oct - 22 Oct
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
No reviews
The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
18 Oct - 22 Oct
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
9.6/10 Exceptional! (462 reviews)
Hands down the best place we have stayed. They accommodated to go breakfasts for our tours, arranged taxis, made cappuccino when we were heading out the door. Wonderful experience

Reviewed on 6 Jun 2025

Hotel Lombardia

Hotel Lombardia

3 out of 5
Historic Centre of Florence
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per person
18 Oct - 22 Oct
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
8.2/10 Very Good! (246 reviews)
Needs a elevator for baggage

Reviewed on 22 Jul 2025

Villa Olmi Firenze

Villa Olmi Firenze

4 out of 5
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per person
18 Oct - 22 Oct
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
9.4/10 Exceptional! (723 reviews)
Beautiful property & amazing staff

Reviewed on 8 Jul 2025

Top hotels in Castiglion Fiorentino

Farmhouse in the hills with panoramic view and swimming pool

Farmhouse in the hills with panoramic view and swimming pool

Ristonchia
9.4/10 Exceptional! (66 reviews)
Family vacation
"Was wonderful and beautiful."

Reviewed on 30 Nov 2024

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Farmhouse in the hills with panoramic view and swimming pool
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Poggio alla Sala 10, Montepulciano, SI
Fully refundableReserve now, pay when you stay
The price is €458 per night from 26 Aug to 27 Aug
€458
26 Aug - 27 Aug
includes taxes & fees
9.4/10 Exceptional! (103 reviews)
"The staff were incredibly kind and helpful. I got a flat tire the day I was leaving the hotel and the staff went above and beyond to help me get the tire fixed so I could be on my way. The hotel is beautiful and the food was excellent. I also requested a more private room and the staff changed the ..."

Reviewed on 19 Jul 2025

Precise Tale Poggio Alla Sala
Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

5 out of 5
Localita Piazzano, C.P. 6, Cortona, AR
Fully refundableReserve now, pay when you stay
The price is €558 per night from 16 Aug to 17 Aug
€558
16 Aug - 17 Aug
includes taxes & fees
9.6/10 Exceptional! (215 reviews)
"Would definitely come back! The Italian garden at the property is beautiful."

Reviewed on 9 Jul 2025

Villa di Piazzano - Small Luxury Hotel of the World
See all 6,816 properties in Castiglion Fiorentino
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.

Popular places to visit

Tennis Club Castiglionese

You can take time to visit Tennis Club Castiglionese during your travels to Castiglion Fiorentino. You can enjoy the wineries while in the area.

Tennis Club Castiglionese

What to do in Castiglion Fiorentino

Wine Tasting: a SYRAH that makes you fall in love

Wine Tasting: a SYRAH that makes you fall in love

€30
per adult
Wine Tasting: a SYRAH that makes you fall in love
Montepulciano: Wine Tour and tasting

Montepulciano: Wine Tour and tasting

€52
per adult
100% of travellers recommend
Montepulciano: Wine Tour and tasting
A Classic Tuscan Winery with Lunch in Montepulciano

A Classic Tuscan Winery with Lunch in Montepulciano

€90
per adult
A Classic Tuscan Winery with Lunch in Montepulciano
See all activities in Castiglion Fiorentino

Frequently asked questions

How much does a Castiglion Fiorentino holiday package cost?
Offering great value package deals from €378 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.