Castiglion Fiorentino Vacations from $1,147

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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 $1,695, price is now $1,147 per person
$1,147
per person
Oct 16 - Oct 20
found 6 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,004 reviews)

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Save 100% on your flight
Price was $4,953, price is now $3,137 per person
$3,137
per person
Sep 14 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (154 reviews)
Magical location, pools, staff, property.

Reviewed on Jul 19, 2026

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Price was $2,132, price is now $1,458 per person
$1,458
per person
Oct 4 - Oct 9
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
8.6/10 Excellent! (494 reviews)

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

4 out of 5
Historic Centre of Florence
Price was $2,329, price is now $1,663 per person
$1,663
per person
Oct 4 - Oct 9
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9/10 Wonderful! (1,004 reviews)
Very convenient to explore everything around Florence

Reviewed on Jul 31, 2026

Hotel Palazzo del Capitano Wellness & Relais - Luxury Borgo Capitano Collection

Hotel Palazzo del Capitano Wellness & Relais - Luxury Borgo Capitano Collection

4 out of 5
Save 100% on your flight
Price was $3,169, price is now $2,269 per person
$2,269
per person
Sep 14 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.2/10 Wonderful! (233 reviews)
THE AMAZING LOCATION THE VIEWS OF THE MOUNTAINS AND VALLEYS AND AMAZING POOL (WE DID NOT GET TO USE IT BECAUSE DUE TO THE TEMPERATURE BEING IN THE 60'S) THE RESTAURANT WHICH IS THE NEXT TO THE HOTEL WAS GREAT !!!

Reviewed on Oct 29, 2025

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Stay near popular Castiglion Fiorentino attractions

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.
See properties

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
Cellar Tour & Wine Tasting

Cellar Tour & Wine Tasting

$57
per adult
Cellar Tour & Wine Tasting
Arezzo: Val di Chiana Wine Tasting Experience

Arezzo: Val di Chiana Wine Tasting Experience

$45
per adult
Arezzo: Val di Chiana Wine Tasting Experience
See all activities in Castiglion Fiorentino

Castiglion Fiorentino Hotel Deals

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
$530 nightly
The price is $590 total per night from Aug 4 to Aug 5
$590 total
Aug 4 - Aug 5
Total with taxes and fees
9.6/10 Exceptional! (155 reviews)
"Magical location, pools, staff, property."

Reviewed on Jul 19, 2026

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
$627 nightly
The price is $699 total per night from Aug 30 to Aug 31
$699 total
Aug 30 - Aug 31
Total with taxes and fees
9.8/10 Exceptional! (241 reviews)
"Very clean and very quiet"

Reviewed on Jul 15, 2026

Villa di Piazzano - Small Luxury Hotel of the World
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
$292 nightly
The price is $331 total per night from Aug 16 to Aug 17
$331 total
Aug 16 - Aug 17
Total with taxes and fees
10/10 Exceptional! (300 reviews)
"Beautiful oasis in a beautiful town"

Reviewed on Jul 25, 2026

Monastero di Cortona Hotel & Spa
See all 6,637 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 $1,147 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.