Castiglion Fiorentino Vacations from $902

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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
Save 100% on your flight
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,001 reviews)
An outstanding location, property is very clean..

Reviewed on Jul 15, 2025

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Oct 1 - Oct 7
found 18 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,012 reviews)
The staff is very friendly.

Reviewed on Jul 11, 2025

Grand Hotel Cavour

Grand Hotel Cavour

4 out of 5
Historic Centre of Florence
per person
Sep 21 - Sep 27
found 18 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.2/10 Wonderful! (1,003 reviews)
A wonderful hotel in an excellent location, right in the historic heart of Florence. The rooftop bar is stunning, and the staff were friendly and helpful.

Reviewed on Jul 12, 2025

Via Roma 33 Tuscany Boutique Hotel & Spa - Adults Only

Via Roma 33 Tuscany Boutique Hotel & Spa - Adults Only

4 out of 5
per person
Sep 8 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Florence (FLR)
9.8/10 Exceptional! (26 reviews)
Overall a lovely stay. The staff is very welcoming and accommodating. Rooms are very clean. Pool too cold to swim in even though they said that it was heated. Wirlpool/hot-tub was on the cool side too. Couldn’t get sauna to work properly -however, I should have asked. Restaurant food was very good.

Reviewed on May 12, 2025

Villa Campestri Olive Oil Resort

Villa Campestri Olive Oil Resort

4 out of 5
per person
Sep 8 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Florence (FLR)
9.4/10 Exceptional! (210 reviews)
The property is gorgeous, the staff was very attentive and all the requests were promptly addressed. The room was big and clean but they don’t have AC. During the day can get warm but overnight there were no issues. The food was delicious and the service was outstanding. Overall we highly recommend this property.

Reviewed on Jul 2, 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

Traditional Tuscan Cuisine Cooking Class, Castiglion Fiorentino near Cortona

Traditional Tuscan Cuisine Cooking Class, Castiglion Fiorentino near Cortona

$158
per adult
Traditional Tuscan Cuisine Cooking Class, Castiglion Fiorentino near Cortona
Montepulciano: Wine Tour and tasting

Montepulciano: Wine Tour and tasting

$61
per adult
100% of travellers recommend
Montepulciano: Wine Tour and tasting
WELCOME!

Private visit to the House of Grand Duke Leopold of Tuscany with invitation

$47
per adult
Private visit to the House of Grand Duke Leopold of Tuscany with invitation
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
$412 nightly
The price is $460 total per night from Aug 9 to Aug 10
$460 total
Aug 9 - Aug 10
Total includes taxes and fees
9.4/10 Exceptional! (99 reviews)
"beautiful property. Emanates "tuscany" amid garden and vineyards. Great villa with excellent and well chosen art. Very comfortable and quiet. Nice amenities. Would stay here again. Much appreciated it for its character and charm and of course service."

Reviewed on Jul 7, 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
$583 nightly
The price is $651 total per night from Jul 21 to Jul 22
$651 total
Jul 21 - Jul 22
Total includes taxes and fees
9.6/10 Exceptional! (212 reviews)
"Would definitely come back! The Italian garden at the property is beautiful."

Reviewed on Jul 9, 2025

Villa di Piazzano - Small Luxury Hotel of the World
See all 6,809 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 $902 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.