Castiglion Fiorentino Vacations from $1,015

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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

Price found within the past 48 hours. Click for updated prices.
Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was $1,483, price is now $1,015 per person
$1,015
per person
Jan 10 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
7.4/10 Good! (1,016 reviews)

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Price was $1,385, price is now $1,063 per person
$1,063
per person
Jan 10 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
8.6/10 Excellent! (508 reviews)

The Hoxton, Florence

The Hoxton, Florence

4 out of 5
Historic Centre of Florence
Price was $1,517, price is now $1,082 per person
$1,082
per person
Jan 18 - Jan 25
found 22 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.4/10 Exceptional! (370 reviews)
Staff lovely, chatty, smiley, helpful. Food good if a little limited evening choice if staying more than a few nights (but so many other retaurants around) Bathroom great hot water but decor could be sharper - bit tatty in couple of places. Superior room as the picture, comfy bed and pillows. Trouble with mosquitos which could have been living in the aircon vents (take a swatter and anti bite - may just be a bad year) Good quiet area away from centre but easily walkable, tram very close. It has a bright, welcoming and relaxed atmosphere.

Reviewed on Oct 28, 2026

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Price was $2,071, price is now $1,481 per person
$1,481
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.6/10 Exceptional! (612 reviews)
Everything was wonderful about our stay at The Moon Hotel and Spa. The room was beautiful and clean, the staff were friendly and helpful and it was a great location for sightseeing in Florence. We especially appreciated the very generous breakfast that was always served efficiently and with a smile. We would definitely stay again.

Reviewed on Oct 23, 2026

Hotel Duomo Firenze

Hotel Duomo Firenze

3 out of 5
Historic Centre of Florence
Price was $1,502, price is now $1,108 per person
$1,108
per person
Jan 18 - Jan 25
found 22 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.2/10 Wonderful! (1,003 reviews)
Great location, very clean and beautiful views. Staff was very kind and helpful

Reviewed on Oct 28, 2026

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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.
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What to do in Castiglion Fiorentino

Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

$28
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
Arezzo Gran Tour

Arezzo Gran Tour

$13
per adult
Arezzo Gran Tour
Montepulciano Wine Tasting with typical Tuscan Cold Cuts

Montepulciano Wine Tasting with typical Tuscan Cold Cuts

$51
per adult
Montepulciano Wine Tasting with typical Tuscan Cold Cuts
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Castiglion Fiorentino Hotel Deals

Tuscan Villa, Private Pool, extensive panoramic garden,nr Castiglion Fiorentino.

Tuscan Villa, Private Pool, extensive panoramic garden,nr 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 Oct 7, 2026

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Tuscan Villa, Private Pool, extensive panoramic garden,nr Castiglion Fiorentino.
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
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Villa di Piazzano - Small Luxury Hotel of the World
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Di Poggio Alla Sala, 10 Montepulciano SI
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Precise Tale Poggio Alla Sala
See all 6,495 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.

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

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Frequently asked questions

How much does a Castiglion Fiorentino vacation package cost?
Offering great value package deals from $1,015 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?
If you're hoping to book a cheap Castiglion Fiorentino vacation package, consider planning a trip in January, October and December. You'll typically find better prices on hotels and airfares during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Castiglion Fiorentino?
Castiglion Fiorentino vacations come in all shapes and sizes, but to get a real feel for this place, we'd say 3 days is a good ballpark. In this timeframe, you can fit in top sights like Archaeological Museum and Vasari Loggia along with hidden gems. Don't forget to explore neighborhoods such as Cortona Old Town and Sodo either. If you plan wisely, you can even schedule a day trip or two from Castiglion Fiorentino too.
Is it worth booking a vacation package to Castiglion Fiorentino?
Well known for its walking trails, festivals and culture, a Castiglion Fiorentino vacation offers something for everyone. Be sure to check out key sights like Cassero Tower and Municipal Art Gallery, and consider renting some wheels for day trips to experience 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?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Castiglion Fiorentino.
  2. Work out your budget: Make sure you have enough money to pay for everything from food and transportation to activities and airfares. Your hotel will probably be the biggest expense during your trip to Castiglion Fiorentino.
  3. Use Expedia's trip planning tool to discover Castiglion Fiorentino: Research every aspect of your trip to Castiglion Fiorentino with this handy planner. Invite family or friends to collaborate on a group trip, search for stays or things to do and make bookings.
  4. Determine how many days away: Start by compiling a list of the activities and attractions you want to get to in Castiglion Fiorentino. Then, estimate how long you'll need at each, along with any travel time.
  5. Bundle your accommodations and airfare: After you've nailed down your trip dates and duration, book the ideal Castiglion Fiorentino vacation package for you.
  6. Add on experiences and excursions: Take a look at our travel guide to find some incredible things to do in Castiglion Fiorentino. Book tickets or make reservations before you go to save time and skip the hassle of looking for activities once you arrive.

Does Expedia offer Book Now, Pay Later Castiglion Fiorentino vacation packages?
Jet off on your perfect trip to Castiglion Fiorentino with help from Expedia's Book Now, Pay Later vacations. No need to save up or hold off until the next payday — we've teamed up with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans mean you can spread the cost over 3, 6 or 12 months. With no late payment fees or extra charges, you can easily budget for your trip and snap up cheap deals before they sell out.

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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.