Castiglion Fiorentino Vacations from $760

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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
Save 100% on your flight
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
If one is not there for a fancy hotel room, but for sightseeing, this is a great, clean, bare bones room. It is close to the train station. We were on the 5th floor and had a great view! Breakfast was also on the 5th floor. Close proximity to all the museums and Duomo, 20 minute walk or less to everything. We walked everywhere!

Reviewed on Jun 21, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
Great place to stay, so close to all attractions. Fantastic staff and service. A happy traveller.

Reviewed on Jun 25, 2025

Hotel Bencista

Hotel Bencista

3 out of 5
Save 100% on your flight
per person
Aug 1 - Aug 7
found 19 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
7.2/10 Good! (11 reviews)
Grand Hotel Cavour

Grand Hotel Cavour

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.2/10 Wonderful! (1,003 reviews)
Fantastic people and best view in Florence at night. Breakfast the best in Florence. Would go back in a heart beat

Reviewed on Jun 25, 2025

Palazzo Firenze by Baglioni Hotels & Resorts

Palazzo Firenze by Baglioni Hotels & Resorts

5 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (225 reviews)
It was a beautiful property. For the price the quality of the breakfast could have been better, and we asked for a bag to be mailed and they wouldn’t do it because it was a Sunday. We had hoped to not have to bring it on the train again. Overall, however, the staff was great and the property is beautiful and conveniently located.

Reviewed on May 25, 2025

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Discover the most popular places to visit in Castiglion Fiorentino

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

Agricola Buccelletti Winery

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.

Agricola Buccelletti Winery

Cassero Tower

Find out about the history of Castiglion Fiorentino when you spend time at Cassero Tower. You can enjoy the wineries while in the area.

Cassero Tower

What to do in Castiglion Fiorentino

Montepulciano: Wine Tour and tasting

Montepulciano: Wine Tour and tasting

$60
per adult
100% of travellers recommend
Montepulciano: Wine Tour and tasting
For your personal cooking class in Tuscany

Amazing four courses cooking class in Tuscany

$305
per adult
Amazing four courses cooking class in Tuscany
Hand made Guitar Spaghetti

Private Cooking Class in Tuscany | Hand Made Pasta

$190
per adult
Private Cooking Class in Tuscany | Hand Made Pasta
See all activities in Castiglion Fiorentino

Castiglion Fiorentino Hotel Deals

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 Nov 30, 2024

Get rates
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
$482 nightly
The price is $537 total per night from Jun 30 to Jul 1
$537 total
Jun 30 - Jul 1
Total includes taxes and fees
9.2/10 Wonderful! (94 reviews)
"This place is absolutely stunning and tranquil, with many amenities to enjoy. The spa area is fantastic, and the room was spotless. The staff provided excellent service, and breakfast was simply amazing. I wish I had stayed longer. If I return to Tuscany someday, I would definitely choose to stay ..."

Reviewed on Jun 21, 2025

Precise Tale Poggio Alla Sala
Nuovo Etruria Resort
Nuovo Etruria Resort
Via di S. Martino snc, Montepulciano, SI
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $119 total per night from Jul 10 to Jul 11
$119 total
Jul 10 - Jul 11
Total includes taxes and fees
9/10 Wonderful! (13 reviews)
"The room was very clean. The view from the room is stunning! It is very quiet and relaxing. The resort is facing Montepulciano! The staff is very nice and friendly. I highly recommend it."

Reviewed on Jun 14, 2025

Nuovo Etruria Resort
See all 6,779 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 $760 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.