Castiglion Fiorentino Vacations from ￥314,864
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The Latest Castiglion Fiorentino Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Villa Castiglione
￥319,512
per person
Oct 16 - Oct 23
just found
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
8.6/10 Excellent! (276 reviews)
Absolutely wonderful stay, newly refurbished pool, gorgeous airy room, staff were incredibly helpful and informative, great food- but the location!!! Wow wow wow!!! Fantastic value for money and feels like you’re in the heart of tuscany but in easy reach of Florence with a car.
Reviewed on Jul 15, 2026
Villa Neroli
Coverciano
￥375,273
per person
Oct 16 - Oct 23
just found
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
9.6/10 Exceptional! (659 reviews)
This is overall a great property in every respect. Highly recommended.
The only advice to other visitors is to plan for their lunch and dinner if they want more variety. The hotel restaurant is great and we dined there several times. But there are not many other good choices within walking distance from the hotel.
Reviewed on Sep 10, 2026
Find the Best Castiglion Fiorentino Vacation Packages
Castiglion Fiorentino Hotel Deals
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
￥108,325
￥120,583 total
Sep 30 - Oct 1
includes taxes & fees
9.8/10 Exceptional! (248 reviews)
"Feels overpriced. Not much things to do but just chill. View is less"
Reviewed on Sep 13, 2026
Nuovo Etruria Resort
Via di S. Martino snc Montepulciano SI
Fully refundable
￥17,802
￥20,295 total
Sep 22 - Sep 23
includes taxes & fees
9.2/10 Wonderful! (128 reviews)
"Great hotel near the town."
Reviewed on Sep 9, 2026
Precise Tale Poggio Alla Sala
Via Di Poggio Alla Sala, 10 Montepulciano SI
Fully refundableReserve now, pay when you stay
￥78,795
￥87,743 total
Sep 30 - Oct 1
includes taxes & fees
9.6/10 Exceptional! (167 reviews)
"Incredible stay in a beautiful location. The staff were amazing and the hospitality was top tier. We will most definitely be back. The recommendations given were brilliant and the room was stunning along with the rest of the hotel. We didn’t dine in the restaurant but our breakfast each morning was ..."
Reviewed on Sep 5, 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 spend time at Cassero Tower. You can enjoy the wineries while in the area.
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.
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.
Archaeological Museum
9.6/10 (5 reviews)
You can browse the exhibits at Archaeological Museum, a museum with a storied past, during your trip to Castiglion Fiorentino. You can enjoy the wineries while in the area.
What to do in Castiglion Fiorentino
Montepulciano Wine Tasting in the Tuscan Countryside
￥4,618
per adult
Oil museum and oil mill in Tuscany: tour and tasting
￥3,709
per adult
Frequently asked questions
How much does a Castiglion Fiorentino vacation package cost?
Offering great value package deals from ￥314,864 on Expedia, you'll be surprised at how little a vacation 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 vacation 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 vacation 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 vacation package to Castiglion Fiorentino?
Well known for its nightlife, views and walking trails, a Castiglion Fiorentino vacation 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 vacation package well in advance.
Is it cheaper to book a Castiglion Fiorentino vacation as a package?
Expedia vacation 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 personalized Castiglion Fiorentino vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation 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 favorite time of year and the available activities will also help you decide when to vacation in Castiglion Fiorentino.
- Work out your budget: Ensure you have enough money to cover everything from food and transportation to activities and flights. Your accommodations 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 customized Castiglion Fiorentino vacation package.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
