Castiglion Fiorentino Vacation Packages

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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.

Top Castiglion Fiorentino Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Maxim Axial

Maxim Axial

3 out of 5
Duomo
per person
Jul. 12 - Jul. 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
8.4/10 Very Good! (1,002 reviews)
Clean , friendly staff , located in the center of city so very convenient to go around city lot of food options available around

Reviewed on Apr. 27, 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Santa Maria Novella
Save 100% on your flight
per person
Jul. 12 - Jul. 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.6/10 Exceptional! (436 reviews)
Wonderful stay. Staff very warm and friendly. Celebrating daughter's birthday, they offered a bottle of prosecco but we can't handle our booze in such quantity so we got some lovely juice drinks. The rooms are spotless, bedding and linens top quality, location is very quiet. Breakfast was excellent with a very large selection of items. We did not have room for the hot selections but they looked delicious. Wish we could have stayed more than one night, will certainly be our top choice for our next stay. Location is very walkable to the main train station and to the city center, but set back enough that you have a quiet neighborhood feel.

Reviewed on Apr. 26, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Santa Croce
per person
Jun. 27 - Jul. 1
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
7.8/10 Good! (1,006 reviews)
Pleasant stay, clean, convenient, lovely staffs and always helpful but could be helpful if we have kettle for coffee or tea in the rooms or even in the dining room. Otherwise we love stay there. No complaints at all.

Reviewed on Apr. 30, 2025

Hotel Duomo Firenze

Hotel Duomo Firenze

3 out of 5
Duomo
per person
Jun. 2 - Jun. 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9/10 Wonderful! (972 reviews)
The staff was great and so helpful. The location was perfect. Everything walkable from hotel. Great experience staying by Duomo.

Reviewed on Apr. 28, 2025

Glance Hotel In Florence

Glance Hotel In Florence

4 out of 5
San Lorenzo
per person
Jun. 5 - Jun. 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.4/10 Exceptional! (1,001 reviews)
Very good breakfast included with the room. Very nice shower and room was clean and comfortable. The hotel is walkable to all the major tourist areas. Take food available very close to the hotel. Walkable to the train station.

Reviewed on Apr. 30, 2025

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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! (65 reviews)
Family vacation
"Was wonderful and beautiful."

Reviewed on Nov. 30, 2024

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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
The price is CA $551 per night from May 25 to May 26
CA $551
CA $615 total
includes taxes & fees
May 25 - May 26
"This is a beautiful location and the facilities are stunning. Really everything is picture perfect and you are only 20 minutes from Montepulciano and 30 minutes from Pienza. Both are amazing to explore and offer excellent dining options. The concierge recommended Tuscan Sweet Dreams to take us to ..."

Reviewed on Apr. 8, 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
The price is CA $873 per night from May 3 to May 4
CA $873
CA $973 total
includes taxes & fees
May 3 - May 4
9.6/10 Exceptional! (202 reviews)
"The Villa di Piazzano is stunning down to the smallest detail. The staff is attentive, pleasant and helpful. The food and wine at the onsite restaurant was some of the best we had on our 23-day trip across Italy. One of our favorite stays for sure!"

Reviewed on Oct. 29, 2024

Villa di Piazzano - Small Luxury Hotel of the World
See all 6,671 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.

All Inclusive Vacations

All Inclusive Vacations

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Frequently asked questions

How much does a Castiglion Fiorentino vacation package cost?
Offering great value package deals from CA $1,498 on Expedia, you’ll be thrilled with how little a vacation to Castiglion Fiorentino costs! Expedia’s packages make travel planning easier and save you more.
What are the cheapest months to go to Castiglion Fiorentino?
To score cheap Castiglion Fiorentino vacation packages, plan your trip outside of busy periods like public holidays and major festivals. You’ll typically find lower prices and better availability in the off-season or when it’s less busy.
How many days is enough for Castiglion Fiorentino?
With about 3 days, you’ll have enough time to experience popular neighbourhoods like Cortona Old Town and Sodo during your Castiglion Fiorentino vacation. Make sure to also add Eremo Le Celle and Belvedere to your sightseeing list. Looking for more adventures? Consider venturing outside of Castiglion Fiorentino on tours and day trips.
Is it worth booking a vacation package to Castiglion Fiorentino?
Whether you’re looking to explore top attractions like Cassero Tower and Municipal Art Gallery on your Castiglion Fiorentino vacation, or coming for its excellent nightlife, views and walking trails, there’s something for everyone here. With so many things to see and do, you’ll soon find out why so many families think Castiglion Fiorentino is a good vacation destination.
How to find the best Castiglion Fiorentino package deals?
Use Expedia’s filters to help you find some tempting Castiglion Fiorentino package deals. When you begin your search, simply set your maximum budget and then order the results by “Price: low to high.” If you’re looking to save, plan your trip for midweek, or browse for Castiglion Fiorentino package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it’s usually best to book your vacation package as soon as possible.
Is it cheaper to book a Castiglion Fiorentino vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You’ll usually snag a better deal than booking each component individually. And you’ll still have the flexibility to create a personalized Castiglion Fiorentino vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Castiglion Fiorentino?
If you’re considering a spur-of-the-moment Castiglion Fiorentino vacation, check out our last-minute deals that can be booked up to one week before you take off. Don’t want to leave things to the last minute? You can find amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to Castiglion Fiorentino?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Castiglion Fiorentino.
  2. Calculate your budget: Ensure you have enough money to pay for everything from meals and transportation to flights and activities. Your hotel will likely be the biggest expense during your trip to Castiglion Fiorentino.
  3. Decide your trip length: Think about how long you’d like to spend discovering Castiglion Fiorentino. Plan your itinerary so you can get to all the experiences and attractions you’re interested in without rushing.
  4. Combine your airfare and accommodations: Once you’ve settled on your dates and duration, lock in the perfect Castiglion Fiorentino vacation package for you.

What to do in Castiglion Fiorentino

Montepulciano: Wine Tour and tasting

Montepulciano: Wine Tour and tasting

CA $82
per adult
100% of travellers recommend
Montepulciano: Wine Tour and tasting
Foiano della Chiana

Walk in the heart of Foiano della Chiana and its surroundings

CA $61
per adult
Walk in the heart of Foiano della Chiana and its surroundings
The Villa

Cellar Tour & Wine Tasting

CA $79
per adult
Cellar Tour & Wine Tasting
See all activities in Castiglion Fiorentino
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.