Castiglion Fiorentino Vacations from $965

Book a Hotel + Flight or Car together to unlock savings

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

Historic Centre of Florence
$965
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
Clean room, convenient location. has AC and lift. Breakfast was ok. Would stay again

Reviewed on Aug 12, 2026

Eden Rock Resort

Eden Rock Resort

Save 100% on your flight
$1,808
per person
Sep 22 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.8/10 Exceptional! (109 reviews)
This was a beautiful property about 10 mins away from Florence. You get the beauty of Tuscany without having to go too far. The hotel only has 12 rooms and everyone knows you by name. We traveled with 2 kids and the rooms were very spacious. Staff are wonderful, Onsite restaurant was great. Views were breathtaking. We didn't have a car, and the hotel was able to help us with cabs easily. Service was excellent and we would highly recommend this hotel!

Reviewed on Jul 18, 2026

Aurum Firenze

Aurum Firenze

Historic Centre of Florence
$1,394
per person
Sep 14 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
7.4/10 Good! (1,008 reviews)
Room very small, no chairs inside, ants everywhere, including the breakfast area. Quadruple room has a double bed and a single bed, apparently this was the biggest room in the hotel. We book for 4 people ( 2 adults and 2 children 12 and 16 and they had to squeeze in a single bed.

Reviewed on Aug 12, 2026

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence
Save 100% on your flight
$1,991
per person
Oct 7 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9/10 Wonderful! (1,006 reviews)
We had a wonderful stay at La Scaletta in Florence! The hotel was extremely clean, and the staff was always friendly, welcoming, and very helpful throughout our stay. The location is fantastic, just steps from the Ponte Vecchio, with so many great shops, restaurants, and beautiful sights within easy walking distance. One of the things we loved most was the combination of history and modern comfort. Staying in such a beautiful historic building, surrounded by gorgeous frescoes and architectural details, made the experience feel very special, while the rooms still had a fresh, modern vibe. The terrace bar was another highlight and a wonderful place to relax and enjoy Florence. Beautiful hotel, excellent location, and great service. We would definitely recommend La Scaletta and would happily stay here again!

Reviewed on Aug 12, 2026

Grand Hotel Cavour

Grand Hotel Cavour

Historic Centre of Florence
$1,461
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.2/10 Wonderful! (1,001 reviews)
Fantastic location, lovely rooftop terrace - my only comment would be that the rooms need somewhere to sit down.

Reviewed on Aug 13, 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

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

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

Agricola Buccelletti Winery

10.0/10 (2 reviews)
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.
See properties

Archaeological Museum

9.6/10 (5 reviews)
You can browse the exhibits at Archaeological Museum, a museum with a storied past, during your trip to Castiglion Fiorentino. You can enjoy the wineries while in the area.
See properties

Vasari Loggia

10.0/10 (2 reviews)
You can find out about the history of Castiglion Fiorentino with a trip to Vasari Loggia. You can enjoy the wineries while in the area.
See properties

Municipal Art Gallery

10.0/10 (1 review)
You can study the exhibits at Municipal Art Gallery, a museum with a storied past, 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

$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

Via Poggio alla Sala 10 Montepulciano SI
Fully refundableReserve now, pay when you stay
$527 nightly
$587 total
Aug 18 - Aug 19
Total with taxes and fees
9.6/10 Exceptional! (159 reviews)
"Precise Tale Poggio Alla Sala is a beautiful, peaceful property in a stunning and remote location near Montepulciano. The rooms and entire establishment were exceptionally clean and well maintained. The staff were friendly and welcoming, and the property is especially family- and kid-friendly, making ..."

Reviewed on Aug 12, 2026

Precise Tale Poggio Alla Sala
Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

Localita Piazzano, C.P. 6 Cortona AR
$637 nightly
$710 total
Aug 17 - Aug 18
Total with taxes and fees
Villa di Piazzano - Small Luxury Hotel of the World
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
$294 nightly
$333 total
Aug 30 - Aug 31
Total with taxes and fees
Monastero di Cortona Hotel & Spa
See all 6,494 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

Frequently asked questions

How much does a Castiglion Fiorentino vacation package cost?
Offering great value package deals from $965 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.