Castiglion Fiorentino Vacations from $1,250

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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 $1,844, price is now $1,250 per person
$1,250
per person
Oct 6 - Oct 10
found 3 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
Very centrally located. We enjoyed our stay and would recommend it. Only issue was you could smell the drains in room 203. They tried to get rid of the smell but couldn’t. Avoid this room and you will be fine.

Reviewed on Jul 15, 2026

L'Andana

L'Andana

5 out of 5
Price was $2,886, price is now $2,046 per person
$2,046
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Florence (FLR)
9.4/10 Exceptional! (91 reviews)
Breathtaking views of the Tuscan countryside, as well as incredibly attentive staff.

Reviewed on Jun 9, 2026

Grand Hotel Cavour

Grand Hotel Cavour

4 out of 5
Historic Centre of Florence
Price was $2,266, price is now $1,610 per person
$1,610
per person
Aug 31 - Sep 4
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.2/10 Wonderful! (1,000 reviews)
Excellent room. Excellent breakfast. Excellent staff. Loved everything about the hotel. And what a bar and view, highly recommended.

Reviewed on Jul 17, 2026

Residenza Florentia

Residenza Florentia

1 out of 5
Historic Centre of Florence
Price was $1,776, price is now $1,275 per person
$1,275
per person
Sep 28 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
8.4/10 Very Good! (53 reviews)
Staff was helpful, the property was not very well maintained.

Reviewed on Jun 1, 2026

Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

5 out of 5
Price was $2,939, price is now $2,110 per person
$2,110
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Florence (FLR)
9.4/10 Exceptional! (207 reviews)
Borgo refers to something like little village and that’s what this property is. A cluster of beautiful stone buildings and gravel drives surrounded by acres of olive and lavender. Beautifully appointed common and areas in rooms. Excellent restaurant with elevated cuisine. Beautiful pool. Distance skyline view of Sienna, Really no negatives. Would definitely come back.

Reviewed on Jul 15, 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.
See properties

What to do in Castiglion Fiorentino

Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

$29
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

$46
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
$545 nightly
The price is $607 total per night from Aug 15 to Aug 16
$607 total
Aug 15 - Aug 16
Total with taxes and fees
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
$618 nightly
The price is $689 total per night from Jul 25 to Jul 26
$689 total
Jul 25 - Jul 26
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
A Point Arezzo Park Hotel

A Point Arezzo Park Hotel

4 out of 5
Loc. Battifolle, 36/T Arezzo AR
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $107 total per night from Aug 5 to Aug 6
$107 total
Aug 5 - Aug 6
Total with taxes and fees
7.6/10 Good! (165 reviews)
"Well, having travelled extensively for the past 13 years, this Hotel must be the coldest I have ever stayed in. It was December, but there was no heating on in the lobby area or the dining area so everyone had to wear coats or thick jumpers while eating their meals. The showers were not particularly ..."

Reviewed on Dec 3, 2025

A Point Arezzo Park Hotel
See all 6,623 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 $1,250 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.