Castiglion Fiorentino Vacations from $1,157

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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 Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,756, price is now $1,157 per person
$1,157
per person
Aug 4 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
7.6/10 Good! (1,011 reviews)
The hotel was conveniently located, and the service was good. Overall, it was a pleasant stay. However, I hope the hotel improves its Wi-Fi coverage, as the connection can become unstable when multiple guests are accessing the network.

Reviewed on Jun 5, 2026

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Save 100% on your flight
Price was $3,808, price is now $2,623 per person
$2,623
per person
Jul 29 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.6/10 Exceptional! (143 reviews)
What a nice place to stay and enjoying Tuscany region!! Lovely place and atmosphere!! We definitely love to come back and stay more time for next visit!!

Reviewed on Jun 13, 2026

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was $1,763, price is now $1,159 per person
$1,159
per person
Aug 4 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
7.6/10 Good! (1,025 reviews)
5 mins from train station. 2 min walk to Mercato Central, stores all around. Breakfast from 7-10am. They keep it clean and they offer variety. Very nice staff. 100% recommended. Just be prepared for a very small shower :-)

Reviewed on Jun 16, 2026

Hotel Duomo Firenze

Hotel Duomo Firenze

3 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $2,647, price is now $1,742 per person
$1,742
per person
Sep 6 - Sep 12
found 17 hours ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.2/10 Wonderful! (1,003 reviews)
Wonderful front desk staff! Could not be more conveniently located and view was beautiful. Room was fine - but a bit noisy because it was on same floor as front desk and breakfast area.

Reviewed on Jun 14, 2026

Hotel Annabella Roof Terrace

Hotel Annabella Roof Terrace

3 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $2,310, price is now $1,569 per person
$1,569
per person
Sep 6 - Sep 12
found 17 hours ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
8.6/10 Excellent! (139 reviews)
Xavi was the best. Outstanding customer service. Exceptional .

Reviewed on Jun 11, 2026

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Stay near popular Castiglion Fiorentino attractions

Cassero Tower

9.4/5 (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.
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Castiglion Fiorentino Hotel Deals

Spacious Tuscan Villa with Large Pool near Castiglion Fiorentino.

Spacious Tuscan Villa with Large Pool near Castiglion Fiorentino.

Castiglion Fiorentino
9.8/10 Exceptional! (40 reviews)
"This villa has breathtaking views and a gorgeous peaceful pool area. We were travelling as a family with our adult children and their partners. We were 7 in total and there was plenty of room for us both outside and in. The kitchen is very well equipped with modern appliances and plentiful dishware. ..."

Reviewed on Jun 14, 2026

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Spacious Tuscan Villa with Large Pool near 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
$642 nightly
The price is $715 total per night from Jun 24 to Jun 25
$715 total
Jun 24 - Jun 25
Total with taxes and fees
9.8/10 Exceptional! (237 reviews)
"The Villa is not only one of the most beautiful places on earth but also comfortable warm and inviting. The accommodations are gorgeous and the food is magnificent! The staff is a dream~ so kind and personable. I highly recommend as it will be a trip of a lifetime !!!!"

Reviewed on Jun 9, 2026

Villa di Piazzano - Small Luxury Hotel of the World
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
$410 nightly
The price is $458 total per night from Jun 22 to Jun 23
$458 total
Jun 22 - Jun 23
Total with taxes and fees
9.6/10 Exceptional! (145 reviews)
"What a nice place to stay and enjoying Tuscany region!! Lovely place and atmosphere!! We definitely love to come back and stay more time for next visit!!"

Reviewed on Jun 13, 2026

Precise Tale Poggio Alla Sala
See all 6,615 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 $1,157 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.