Castiglion Fiorentino Vacations from $1,144

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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
Price was $1,806, price is now $1,144 per person
$1,144
per person
Sep 28 - Oct 3
found 13 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Florence (FLR)
7.4/10 Good! (1,008 reviews)
It was not entirely clean, the staff don't do much. Breakfast is from the day before. Air conditioning excellent.

Reviewed on Jul 3, 2026

Palace Hotel

Palace Hotel

4 out of 5
Save 100% on your flight
Price was $2,575, price is now $1,619 per person
$1,619
per person
Aug 21 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.2/10 Wonderful! (131 reviews)
Staff was very nice, breakfast spread was great. Our room unfortunately felt like a let down. It was smaller than expected, had a mildew scent, the toilet constantly ran, and the AC did not work very well.

Reviewed on Jul 2, 2026

Park Hotel Villa Ariston

Park Hotel Villa Ariston

4 out of 5
Save 100% on your flight
Price was $2,722, price is now $1,757 per person
$1,757
per person
Aug 21 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
8.8/10 Excellent! (133 reviews)

Il Rivalta - Place of Charme

Il Rivalta - Place of Charme

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $4,393, price is now $2,846 per person
$2,846
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (549 reviews)
The room was spotless, and the service was outstanding! The breakfast offered a great variety, and the staff was friendly!

Reviewed on Jul 6, 2026

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Save 100% on your flight
Price was $2,814, price is now $1,843 per person
$1,843
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.6/10 Exceptional! (147 reviews)
It’s a beautiful property, but be aware that it is secluded and that the restaurant menu is quite limited and after a couple of days, we were happy to go elsewhere. The waiting staff was attentive and nice, front desk not as much (maybe the la guard barrier?)

Reviewed on Jun 19, 2026

Don't see what you're looking for?
See all available trips from Columbus to Castiglion Fiorentino
View all trips

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
$434 nightly
The price is $484 total per night from Aug 3 to Aug 4
$484 total
Aug 3 - Aug 4
Total with taxes and fees
9.6/10 Exceptional! (148 reviews)
"It’s a beautiful property, but be aware that it is secluded and that the restaurant menu is quite limited and after a couple of days, we were happy to go elsewhere. The waiting staff was attentive and nice, front desk not as much (maybe the la guard barrier?)"

Reviewed on Jun 19, 2026

Precise Tale Poggio Alla Sala
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
$92 nightly
The price is $109 total per night from Jul 9 to Jul 10
$109 total
Jul 9 - Jul 10
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
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 11 to Jul 12
$689 total
Jul 11 - Jul 12
Total with taxes and fees
9.8/10 Exceptional! (238 reviews)
"Staff was so friendly and the property is beautiful"

Reviewed on Jun 28, 2026

Villa di Piazzano - Small Luxury Hotel of the World
See all 6,613 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Castiglion Fiorentino vacation package cost?
Offering great value package deals from $1,144 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.